(1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one
ingenol
Conditions | Yield |
---|---|
With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 1.25h; | 76% |
Stage #1: (1aR,2S,5R,5aS,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-1,1,4,7,9-pentamethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one With selenium(IV) oxide; formic acid In 1,4-dioxane at 80℃; for 2h; Inert atmosphere; Stage #2: With sodium hydroxide In 1,4-dioxane; water for 0.5h; Inert atmosphere; | 76% |
With selenium(IV) oxide In 1,4-dioxane; formic acid at 80℃; for 2h; | 70% |
With selenium(IV) oxide; silica gel In tetrahydrofuran at 80℃; for 2h; | 40% |
ingenol monoacetate
ingenol
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 0 - 20℃; Temperature; Solvent; Inert atmosphere; | 74% |
ingenol 3,5,20-triacetate
ingenol
Conditions | Yield |
---|---|
With sodium methylate In methanol | 71% |
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
A
ingenol
Conditions | Yield |
---|---|
With perchloric acid In methanol for 1h; | A 66% B n/a |
ingenol-3,4:5,20-diacetonide
A
ingenol
B
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
Conditions | Yield |
---|---|
With perchloric acid In methanol for 0.75h; Further byproducts given; | A 31% B 3% C 18% |
C43H47N3O9
ingenol
Conditions | Yield |
---|---|
With sodium methylate In methanol |
ingenol 3-(2,4,6,8,10)-tetradecapentaenoate
ingenol
Conditions | Yield |
---|---|
With sodium methylate In methanol |
ingenol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.5h; |
ingenol
Conditions | Yield |
---|---|
With potassium hydroxide In methanol for 0.5h; Yield given; |
A
ingenol
Conditions | Yield |
---|---|
With sodium methylate In methanol for 0.666667h; Ambient temperature; Yield given. Yields of byproduct given; |
3,4-O-isopropylidene-20-deoxyingenol
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 2: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 21 steps 1.1: 98 percent / KH / tetrahydrofuran / Heating 2.1: 76 percent / Hoveyda-Grubbs catalyst / toluene / 30 h / Heating 3.1: aq. HCl / tetrahydrofuran / 3 h / Heating 4.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C 5.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 5.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 6.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 7.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 8.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 9.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 10.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 11.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 12.1: NaBH4 / methanol / 5 h / 20 °C 13.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 14.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 15.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 16.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 17.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 18.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 19.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 20.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 21.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C23H32O5
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 2: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 3: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 4: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 5: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 6: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 7: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C28H34O4
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 2: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 3: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 4: NaBH4 / methanol / 5 h / 20 °C 5: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 6: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 7: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 8: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 9: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 10: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 11: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 12: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 13: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 18 steps 1.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C 2.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 2.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 3.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 4.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 5.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 6.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 7.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 8.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 9.1: NaBH4 / methanol / 5 h / 20 °C 10.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 11.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 12.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 13.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 14.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 15.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 16.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 17.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 18.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C24H34O7S
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 2: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 3: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 4: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 5: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 6: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C28H36O3
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 16 steps 1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 2: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 3: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 4: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 5: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 6: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 7: NaBH4 / methanol / 5 h / 20 °C 8: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 9: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 10: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 11: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 12: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 13: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 14: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 15: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 16: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C28H38O4
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 17 steps 1.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 1.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 2.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 3.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 4.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 5.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 6.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 7.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 8.1: NaBH4 / methanol / 5 h / 20 °C 9.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 10.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 11.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 12.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 13.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 14.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 15.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 16.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 17.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C28H34O5
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 2: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 3: NaBH4 / methanol / 5 h / 20 °C 4: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 5: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 6: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 7: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 8: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 9: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 10: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 11: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 12: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C29H36O4S
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 2: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 3: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 4: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 5: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C28H36O4
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 15 steps 1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 2: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 3: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 4: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 5: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 6: NaBH4 / methanol / 5 h / 20 °C 7: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 8: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 9: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 10: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 11: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 12: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 13: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 14: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 15: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C28H34O4
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 2: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 3: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 4: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 5: NaBH4 / methanol / 5 h / 20 °C 6: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 7: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 8: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 9: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 10: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 11: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 12: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 13: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 14: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 4 h / Heating 2: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 3: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 4: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C29H36O6S
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 2: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 3: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C29H36O6S
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 2: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 3: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 4: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C30H40O5
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 19 steps 1.1: aq. HCl / tetrahydrofuran / 3 h / Heating 2.1: 1.9 g / NaBH4 / ethanol; tetrahydrofuran / 0.25 h / 0 °C 3.1: PPh3; imidazole; I2 / tetrahydrofuran / 3 h / 0 °C 3.2: 94 percent / t-BuOK / tetrahydrofuran; dimethylsulfoxide / 20 °C 4.1: 49 percent / SeO2; aq. AcOH; t-BuOOH / CH2Cl2; decane / 2 h / 20 °C 5.1: 74 percent / Dess-Martin periodinane / CH2Cl2 / 1.5 h / -40 - 10 °C 6.1: 74 percent / aq. RhCl3 / aq. ethanol / 0.58 h / 115 °C 7.1: 94 percent / P(OMe)3; O2; t-BuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.75 h / -40 °C 8.1: 73 percent / VO(acac)2; t-BuOOH / benzene; decane / 10 h / 20 °C 9.1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 10.1: NaBH4 / methanol / 5 h / 20 °C 11.1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 12.1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 13.1: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 14.1: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 15.1: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 16.1: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 17.1: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 18.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 19.1: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C28H34O6
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1: 72 percent / Et3N / CH2Cl2 / 1 h / -10 - -5 °C 2: NaBH4 / methanol / 5 h / 20 °C 3: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 4: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 5: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 6: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 7: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 8: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 9: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 10: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 11: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
C31H40O6
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 2: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 3: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 4: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 5: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 6: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 7: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 8: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
ingenol
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1: 39 mg / PPTS / CH2Cl2 / 0.5 h / Heating 2: 90 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2 / 18 h / 20 °C 3: 96 percent / Et3N / CH2Cl2 / 0.75 h / -78 °C 4: 76 percent / Li2CO3 / dimethylformamide / 5 h / 55 °C 5: 97 percent / (NH4)6Mo7O24; aq. H2O2 / aq. ethanol / 6 h / 20 °C 6: 47 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 5 h / Heating 7: 76 percent / Na2HPO4; Na(Hg) / methanol / 0.42 h / -20 - -10 °C 8: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 20 °C 9: 40 percent / SeO2/SiO2 / tetrahydrofuran / 2 h / 80 °C View Scheme |
Conditions | Yield |
---|---|
With pyridine Inert atmosphere; | 96% |
In pyridine for 24h; | 89% |
With dmap In pyridine for 16h; Etherification; | 86% |
Conditions | Yield |
---|---|
In pyridine | 95% |
With pyridine Ambient temperature; Yield given; |
ingenol
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 20℃; for 1.5h; | 95% |
In N,N-dimethyl-formamide for 0.75h; | 75% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 14h; Mitsunobu Displacement; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Solvent; Temperature; Reagent/catalyst; Mitsunobu Displacement; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
In pyridine | 90% |
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1.5h; | A 87% B 3.62% |
methanol
ingenol
Conditions | Yield |
---|---|
With perchloric acid at 20℃; for 16h; Addition; rearrangement; | 84% |
ingenol
acetone
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; for 1.5h; Product distribution / selectivity; | 81% |
With toluene-4-sulfonic acid for 0.133333h; | 80% |
With methanesulfonic acid In tetrahydrofuran at 45℃; | 80% |
ingenol
acetone
A
(6S,6aR,7aR,9R,9aS,12S,12aR,12bR)-12,12a-dihydroxy-2,2,7,7,9,11-hexamethyl-4,6,6a,7,7a,8,9,12,12a,12b-decahydro-6,9a-methanocyclopenta[9,10]cyclopropa[5,6]cyclodeca[1,2-d][1,3]dioxin-13-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 20℃; for 0.5h; Overall yield = 73 %; | A 73% B 4.5% |
Conditions | Yield |
---|---|
With PS-triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 2h; Substitution; | 67% |
ingenol
phenyl isocyanate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 2h; Acylation; | 51% |
In dichloromethane; N,N-dimethyl-formamide at 20℃; for 5.33h; | 45.4% |
Conditions | Yield |
---|---|
Stage #1: ingenol; methyl 2-(benzo[d]thiazol-2-ylsulfonyl)acetate With triphenylphosphine In benzene at 0℃; for 0.0833333h; Stage #2: With di-isopropyl azodicarboxylate In benzene at 0 - 20℃; for 12.5h; | 51% |
ingenol
di-tert-butylsilyl bis(trifluoromethanesulfonate)
ingenol-5,20-(di(tert-butyl)silylene) ether
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In N,N-dimethyl-formamide at 0 - 20℃; | 50% |
(Z)-2-methyl-2-butenoic anhydride
ingenol
ingenol 3,20-di-angelate
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 1h; | 48% |
ingenol
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide for 22h; | 47% |
ingenol
n-butyl isocyanide
Conditions | Yield |
---|---|
Stage #1: ingenol; n-butyl isocyanide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3.66h; Stage #2: With triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 18h; | 46% |
Conditions | Yield |
---|---|
With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at -18℃; for 72h; Acylation; | A 42% B 18% |
Conditions | Yield |
---|---|
With potassium carbonate In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; | A 42% B 19% |
ingenol
Conditions | Yield |
---|---|
Stage #1: ingenol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrabutylammomium bromide In dichloromethane at 20℃; for 0.0833333h; pH=8.6; Inert atmosphere; Stage #2: With N-chloro-succinimide In dichloromethane at 20℃; for 12h; pH=8.6; Reagent/catalyst; Solvent; pH-value; Inert atmosphere; | 35% |
ingenol
N-(4-chlorophenyl)-N-methylcarbamyl chloride
Conditions | Yield |
---|---|
Stage #1: ingenol; N-(4-chlorophenyl)-N-methylcarbamyl chloride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 48h; | 19.98% |
ingenol
2-chloro-5-(trifluoromethyl)pyrimidine
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 39.5h; | 5% |
ingenol
benzyl isothiocyanate
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; | 4.7% |
The Ingenol, with the CAS registry number 30220-46-3, is also known as AC1Q6DXY. This chemical's molecular formula is C20H28O5 and molecular weight is 348.43332. Its IUPAC name is called (1aR,2S,5R,5aR,6S,8aS,9R,10aR)-5,5a,6-trihydroxy-4-(hydroxymethyl)-1,1,7,9-tetramethyl-1a,2,5,5a,6,9,10,10a-octahydro-1H-2,8a-methanocyclopenta[a]cyclopropa[e][10]annulen-11-one.
Physical properties of Ingenol: (1)ACD/LogP: -1.01; (2)ACD/LogD (pH 5.5): 3; (3)ACD/LogD (pH 7.4): 3; (4)ACD/BCF (pH 5.5): 103; (5)ACD/BCF (pH 7.4): 103; (6)ACD/KOC (pH 5.5): 960; (7)ACD/KOC (pH 7.4): 960; (8)#H bond acceptors: 5; (9)#H bond donors: 4; (10)#Freely Rotating Bonds: 5; (11)Index of Refraction: 1.625; (12)Molar Refractivity: 91.992 cm3; (13)Molar Volume: 260.055 cm3; (14)Surface Tension: 62.369 dyne/cm; (15)Density: 1.34 g/cm3; (16)Flash Point: 284.654 °C; (17)Enthalpy of Vaporization: 91.764 kJ/mol; (18)Boiling Point: 523.785 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CC1CC2C(C2(C)C)C3C=C(C(C4(C1(C3=O)C=C(C4O)C)O)O)CO
(2)InChI: InChI=1S/C20H28O5/c1-9-7-19-10(2)5-13-14(18(13,3)4)12(17(19)24)6-11(8-21)16(23)20(19,25)15(9)22/h6-7,10,12-16,21-23,25H,5,8H2,1-4H3
(3)InChIKey: VEBVPUXQAPLADL-UHFFFAOYSA-N
About|Contact|Cas|Product Name|Molecular|Country|Encyclopedia
Message|New Cas|MSDS|Service|Advertisement|CAS DataBase|Article Data|Manufacturers | Chemical Catalog
©2008 LookChem.com,License: ICP
NO.:Zhejiang16009103
complaints:service@lookchem.com Desktop View