2-(3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl)-1,4-dimethoxy-3-methylnaphthalene
menaquinone-7
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In water; acetonitrile at 20℃; for 4.08333h; | 80% |
With ammonium cerium (IV) nitrate In acetonitrile at 20℃; for 4.08333h; | 80% |
With ammonium cerium (IV) nitrate In water; acetonitrile at 0℃; for 0.75h; | 72% |
With ammonium cerium (IV) nitrate In dichloromethane; water; acetonitrile at 0℃; for 0.75h; | 0.753 g |
C50H74O2
menaquinone-7
Conditions | Yield |
---|---|
With ammonium cerium (IV) nitrate In dichloromethane; water; acetonitrile at 0℃; for 0.25h; | 72% |
2-(chloromethyl)-3-methylnaphthalene-1,4-dione
trimethylaluminum
menaquinone-7
Conditions | Yield |
---|---|
Stage #1: C33H52; trimethylaluminum With zirconocene dichloride In toluene at 0℃; for 1h; Stage #2: 2-(chloromethyl)-3-methylnaphthalene-1,4-dione With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium In tetrahydrofuran; hexane at -20℃; for 1h; | 65% |
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 3.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 5.2: -78 - 20 °C 6.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 7.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 9.2: 4.5 h / 0 °C / Inert atmosphere 10.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 2.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 3.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 5.2: -78 - 20 °C 6.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 8.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 10.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 10.2: 5 h / 0 °C / Inert atmosphere 11.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 11 steps 1.1: selenium(IV) oxide; salicylic acid; tert.-butylhydroperoxide / dichloromethane / 14 h / 0 °C 1.2: 2 h 2.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.75 h / -45 - -40 °C 2.2: 2 h / 0 °C 3.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: sodium methylate / methanol / 4 h / 0 °C 5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 7.1: triphenylphosphine; bromine / dichloromethane / 0 °C 8.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 8.2: 12 h / Inert atmosphere 9.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 10.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 11.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme |
E,E,E-12-hydroxyfarnesyl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 3.2: -78 - 20 °C 4.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 5.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 7.2: 4.5 h / 0 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 3.2: -78 - 20 °C 4.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 6.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 8.2: 5 h / 0 °C / Inert atmosphere 9.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: methanesulfonyl chloride; triethylamine / tetrahydrofuran / 0.75 h / -45 - -40 °C 1.2: 2 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium methylate / methanol / 4 h / 0 °C 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: triphenylphosphine; bromine / dichloromethane / 0 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme |
(2E,6E,10E)-3,7,11-trimethyl-12-(phenylsulfonyl)-dodeca-2,6,10-trien-1-yl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 5.2: 4.5 h / 0 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 6.2: 5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
farnesyl bromide
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 5.2: 4.5 h / 0 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 6.2: 5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1.5 h / -78 °C 2.2: -78 - 0 °C 3.1: sodium methylate / methanol / 2 h / 20 °C / pH 12 4.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 7.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 1.2: -78 - 20 °C 2.1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12 3.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: pyridine / N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide / 1.5 h / -78 °C 2.2: 5 h / -78 °C 3.1: sodium methylate; methanol / 2 h / 20 °C 4.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 5.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 7.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
C38H56O4S
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 2.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 4.2: 4.5 h / 0 °C / Inert atmosphere 5.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 3.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 5.2: 5 h / 0 °C / Inert atmosphere 6.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium hydroxide / methanol / 1 h / 20 °C / pH 12 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 3: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-12-(phenylsulfonyl)tetracosa-2,6,10,14,18,22-hexaen-1-ol
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 3.2: 4.5 h / 0 °C / Inert atmosphere 4.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 2.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 4.2: 5 h / 0 °C / Inert atmosphere 5.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 4: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 5: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere 2: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 4: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 5: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
(2E,6E,10E)-12-bromo-3,7,11-trimethyl-2,6,10-dodecatrienyl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 2.2: -78 - 20 °C 3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 6.2: 4.5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 2.2: -78 - 20 °C 3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 4.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 5.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 7.2: 5 h / 0 °C / Inert atmosphere 8.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium methylate / methanol / 4 h / 0 °C 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: triphenylphosphine; bromine / dichloromethane / 0 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme |
(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-ol
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 3.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 3.2: 5 h / 0 °C / Inert atmosphere 4.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: triphenylphosphine; bromine / dichloromethane / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: triphenylphosphine; bromine / dichloromethane / 0 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
1-bromo-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 2.2: 5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 2: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 3: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
phenylsulfonyl hexaprenyl bromide
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 2.2: 4.5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
C62H82O6S2
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 1.2: 4.5 h / 0 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
C56H78O4S
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 1.2: 5 h / 0 °C / Inert atmosphere 2.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
(2E,6E,10E)-3,7,11-trimethyl-12-oxododeca-2,6,10-trien-1-yl acetate
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 4.2: -78 - 20 °C 5.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 7.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 9.2: 5 h / 0 °C / Inert atmosphere 10.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 4.2: -78 - 20 °C 5.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 6.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 7.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 8.2: 4.5 h / 0 °C / Inert atmosphere 9.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.5 h / -10 °C 2.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 3.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 4.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.5 h / -78 °C 4.2: -78 - 20 °C 5.1: sodium hydroxide / methanol; water / 1 h / 20 °C / pH 12 6.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 7.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 8.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 9.1: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme |
1,4-diethoxy-2-methyl-3-[(2E)-3-methyl-4-(phenylsulfonyl)-2-buten-1-yl]naphtalene
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 2.2: 4.5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 2.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 2.2: 5 h / 0 °C / Inert atmosphere 3.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 6.2: -78 - 20 °C 7.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 8.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 9.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 10.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 10.2: 4.5 h / 0 °C / Inert atmosphere 11.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: pyridine / 12 h / 0 - 20 °C / Inert atmosphere 2.1: salicylic acid; selenium(IV) oxide; tert.-butylhydroperoxide / water; dichloromethane / 24 h / 0 - 20 °C 3.1: sodium tetrahydroborate / methanol; tetrahydrofuran / 0.75 h / -10 °C 4.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C / Inert atmosphere 5.1: N,N-dimethyl-formamide / 18 h / 20 °C / Darkness 6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 6.2: -78 - 20 °C 7.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 8.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride; lithium triethylborohydride / tetrahydrofuran / 1.17 h / 0 °C / Inert atmosphere 9.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 10.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.83 h / -20 °C / Inert atmosphere; Cooling with acetone-dry ice 11.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / Inert atmosphere; Cooling with acetone-dry ice 11.2: 5 h / 0 °C / Inert atmosphere 12.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: phosphorus tribromide / tetrahydrofuran / 3 h / 0 °C 2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 2.67 h / -78 °C 2.2: -78 - 20 °C 3.1: sodium hydroxide; water / methanol / 1 h / 20 °C / pH 12 4.1: phosphorus tribromide / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere; Cooling with acetone-dry ice 5.1: sodium hexamethyldisilazane / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / -20 - 0 °C / Inert atmosphere; Cooling with acetone-dry ice 6.1: (1,2-bis(diphenylphosphino)ethane)palladium(II) chloride / tetrahydrofuran / 0.08 h / 0 °C / Cooling with acetone-dry ice; Inert atmosphere 6.2: 4.5 h / 0 °C / Inert atmosphere 7.1: ammonium cerium (IV) nitrate / water; dichloromethane; acetonitrile / 0.25 h / 0 °C View Scheme |
1,4-dimethoxy-2-methylnaphthalene
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2.25 h / 0 °C 2.3: 0.67 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 14 h / Inert atmosphere 4.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 5.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: iodine / chloroform / 6 h / 20 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 2.2: 2.25 h / 0 °C 2.3: 0.67 h / Reflux 3.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 3.2: 14 h / Inert atmosphere 4.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 5.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 6.1: iodine / chloroform / 6 h / 20 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: tin(IV) chloride / 1,2-dichloro-ethane / 20 - 80 °C 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 4 steps 1: tin(IV) chloride / 1,2-dichloro-ethane / 5 h / 80 °C 2: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 3: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 4: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
1,4-dimethoxynaphthalene-3-methyl-2-carboxaldehyde
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2.25 h / 0 °C 1.3: 0.67 h / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 14 h / Inert atmosphere 3.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5.1: iodine / chloroform / 6 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 1.2: 2.25 h / 0 °C 1.3: 0.67 h / Reflux 2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 2.2: 14 h / Inert atmosphere 3.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 4.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 5.1: iodine / chloroform / 6 h / 20 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
(1,4-dimethoxy-3-methylnaphthalen-2-yl)acetaldehyde
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 14 h / Inert atmosphere 2.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4.1: iodine / chloroform / 6 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 14 h / Inert atmosphere 2.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 3.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 4.1: iodine / chloroform / 6 h / 20 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: iodine / chloroform / 6 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 12 h / Inert atmosphere 5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 7.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 2.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 3.1: iodine / chloroform / 6 h / 20 °C 4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 4.2: 12 h / Inert atmosphere 5.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 6.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 7.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 12 h / Inert atmosphere 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
(E)-4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-en-1-ol
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: iodine / chloroform / 6 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: iodine / chloroform / 6 h / 20 °C 3.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 3.2: 12 h / Inert atmosphere 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
4-(1,4-dimethoxy-3-methylnaphthalen-2-yl)-2-methylbut-2-enal
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 12 h / Inert atmosphere 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 1.2: Inert atmosphere 2.1: sodium methylate / methanol / 4 h / 0 °C 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: triphenylphosphine; bromine / dichloromethane / 0 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 2.1: sodium methylate / methanol / 4 h / 0 °C 3.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 4.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 5.1: triphenylphosphine; bromine / dichloromethane / 0 °C 6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 6.2: 12 h / Inert atmosphere 7.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 8.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 9.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: water; sodium dithionite / ethyl acetate; water / Inert atmosphere 2.1: potassium carbonate / acetone / 6 h / Reflux 3.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 4.2: 2.25 h / 0 °C 4.3: 0.67 h / Reflux 5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 14 h / Inert atmosphere 6.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 8.1: iodine / chloroform / 6 h / 20 °C 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 9.2: 12 h / Inert atmosphere 10.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 11.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 12.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 12 steps 1.1: water; sodium dithionite / ethyl acetate / Inert atmosphere 2.1: potassium carbonate / acetone / 6 h / Reflux 3.1: titanium tetrachloride / dichloromethane / 2.17 h / -45 - 0 °C / Inert atmosphere 4.1: potassium tert-butylate / tetrahydrofuran / 0.5 h / 0 °C 4.2: 2.25 h / 0 °C 4.3: 0.67 h / Reflux 5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 5.2: 14 h / Inert atmosphere 6.1: diisobutylaluminium hydride / tetrahydrofuran / 6 h / Inert atmosphere 7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 8.1: iodine / chloroform / 6 h / 20 °C 9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 9.2: 12 h / Inert atmosphere 10.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 11.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 12.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium dithionite / ethyl acetate; water / 0.33 h / 20 °C / Inert atmosphere 2: potassium carbonate / acetone / 6 h / Reflux 3: tin(IV) chloride / 1,2-dichloro-ethane / 20 - 80 °C 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile / 0.75 h / 0 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium dithionite / ethyl acetate; water / 0.33 h / 20 °C / Inert atmosphere 2: potassium carbonate / acetone / 6 h / Reflux 3: tin(IV) chloride / 1,2-dichloro-ethane / 5 h / 80 °C 4: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1 h / -20 °C 5: (1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II); lithium triethylborohydride / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere 6: ammonium cerium (IV) nitrate / water; acetonitrile; dichloromethane / 0.75 h / 0 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: sodium methylate / methanol / 4 h / 0 °C 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: triphenylphosphine; bromine / dichloromethane / 0 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: iodine / chloroform / 6 h / 20 °C 2.1: n-butyllithium / tetrahydrofuran / 0.67 h / -78 °C / Inert atmosphere 3.1: sodium methylate / methanol / 4 h / 0 °C 4.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 5.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 6.1: triphenylphosphine; bromine / dichloromethane / 0 °C 7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 7.2: 12 h / Inert atmosphere 8.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 9.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 10.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: sodium methylate / methanol / 4 h / 0 °C 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: triphenylphosphine; bromine / dichloromethane / 0 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / water; acetonitrile / 4.08 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: sodium methylate / methanol / 4 h / 0 °C 2.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 3.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 4.1: triphenylphosphine; bromine / dichloromethane / 0 °C 5.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 5.2: 12 h / Inert atmosphere 6.1: Dess-Martin periodane; water / dichloromethane; acetonitrile / 20 °C 7.1: hydrazine; potassium hydroxide / diethylene glycol / 4 h / 60 - 215 °C / Inert atmosphere; Reflux 8.1: ammonium cerium (IV) nitrate / acetonitrile / 4.08 h / 20 °C View Scheme |
menaquinone-7
propionic acid anhydride
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dipropionate
Conditions | Yield |
---|---|
With sodium acetate; zinc at 130℃; for 0.5h; | 66% |
With sodium acetate; zinc at 130℃; for 0.5h; | 66% |
menaquinone-7
benzoic acid anhydride
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyl-octacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl dibenzoate
Conditions | Yield |
---|---|
With sodium acetate; zinc at 140℃; for 1h; | 50% |
Stage #1: menaquinone-7; benzoic acid anhydride With sodium acetate; zinc at 140℃; for 1h; Stage #2: With diethylamine In tetrahydrofuran at 20℃; for 1h; | 50% |
menaquinone-7
4-(trifluoromethyl)benzoic anhydride
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalene-1,4-diyl bis(4-(trifluoromethyl)benzoate)
Conditions | Yield |
---|---|
With sodium acetate; zinc at 170℃; for 23h; | 11% |
Stage #1: menaquinone-7; 4-(trifluoromethyl)benzoic anhydride With sodium acetate; zinc at 170℃; for 23h; Stage #2: With diethylamine In tetrahydrofuran at 20℃; for 1h; | 11% |
menaquinone-7
acetic anhydride
1,4-diacetoxy-2-methyl-3-(3,7,11,15,19,23,27-heptamethyl-octacosaheptaen-(2t,6t,10t,14t,18t,22t,26)-yl)-naphthalene
Conditions | Yield |
---|---|
With sodium acetate; zinc | |
With sodium acetate; zinc |
menaquinone-7
3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-2-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C View Scheme |
menaquinone-7
4-((diethoxyphosphoryl)oxy)-2-((2E,6E, 10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme |
menaquinone-7
4-((diethoxyphosphoryl)oxy)-3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme |
menaquinone-7
4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
4-(((tert-butoxycarbonyl)-L-valyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl propionate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme |
menaquinone-7
4-((diethoxyphosphoryl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: triethylamine / dichloromethane / 20 h / 0 - 20 °C View Scheme |
menaquinone-7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
4-(((tert-butoxycarbonyl)glycyl)oxy)-2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-3-methylnaphthalen-1-yl propionate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl 3-((tert-butoxycarbonyl)amino)propanoate
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: dmap; dicyclohexyl-carbodiimide / dichloromethane / 20 h / 20 °C View Scheme |
menaquinone-7
4-((3-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-2-methyl-4-(propionyloxy)naphthalen-1-yl)oxy)-4-oxobutanoic acid
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C 3: dmap / dichloromethane / 3.5 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium acetate; zinc / 0.5 h / 130 °C 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C 3: dmap / dichloromethane / 3.5 h / 20 °C View Scheme |
menaquinone-7
2-((2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaen-1-yl)-4-hydroxy-3-methylnaphthalen-1-yl benzoate
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium acetate; zinc / 1 h / 140 °C 2: lithium hydroxide; water / tetrahydrofuran / 20 h / 50 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: sodium acetate; zinc / 1 h / 140 °C 1.2: 1 h / 20 °C 2.1: lithium hydroxide monohydrate; water / tetrahydrofuran / 20 h / 50 °C View Scheme |
Conditions | Yield |
---|---|
With sodium acetate; zinc for 0.5h; Inert atmosphere; Reflux; |
The CAS register number of Vitamin K2(35) is 2124-57-4. It also can be called 1,4-Naphthalenedione, 2-(3,7,11,15,19,23,27-heptamethyl-2,6,10,14,18,22,26-octacosahept-aenyl)-3-methyl-, (all-E)- and the Systematic name about this chemical is 2-[(2E,6E,10E,14E,18E,22E)-3,7,11,15,19,23,27-heptamethyloctacosa-2,6,10,14,18,22,26-heptaenyl]-3-methylnaphthalene-1,4-dione.
Physical properties about Vitamin K2(35) are: (1)ACD/LogP: 17.05; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 17.04; (4)ACD/LogD (pH 7.4): 17.04; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 20; (12)Polar Surface Area: 34.14Å2; (13)Index of Refraction: 1.532; (14)Molar Refractivity: 209.11 cm3; (15)Molar Volume: 674.7 cm3; (16)Surface Tension: 36 dyne/cm; (17)Density: 0.961 g/cm3; (18)Flash Point: 254.9 °C; (19)Enthalpy of Vaporization: 105.21 kJ/mol; (20)Boiling Point: 720.1 °C at 760 mmHg; (21)Vapour Pressure: 1.38E-20 mmHg at 25 °C.
You can still convert the following datas into molecular structure:
1.SMILES: O=C\2c1c(cccc1)C(=O)/C(=C/2C)C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C
2.InChI: InChI=1/C46H64O2/c1-34(2)18-12-19-35(3)20-13-21-36(4)22-14-23-37(5)24-15-25-38(6)26-16-27-39(7)28-17-29-40(8)32-33-42-41(9)45(47)43-30-10-11-31-44(43)46(42)48/h10-11,18,20,22,24,26,28,30-32H,12-17,19,21,23,25,27,29,33H2,1-9H3/b35-20+,36-22+,37-24+,38-26+,39-28+,40-32+
3.InChIKey: RAKQPZMEYJZGPI-LJWNYQGCBT
4.Std. InChI: InChI=1S/C46H64O2/c1-34(2)18-12-19-35(3)20-13-21-36(4)22-14-23-37(5)24-15-25-38(6)26-16-27-39(7)28-17-29-40(8)32-33-42-41(9)45(47)43-30-10-11-31-44(43)46(42)48/h10-11,18,20,22,24,26,28,30-32H,12-17,19,21,23,25,27,29,33H2,1-9H3/b35-20+,36-22+,37-24+,38-26+,39-28+,40-32+
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