10-(2,3,4-trimethoxy-6-methylphenyl)decan-1-ol
Idebenone
Conditions | Yield |
---|---|
With ammonium peroxydisulfate; nitric acid In water; acetone at 50℃; for 2.16h; | 98% |
Multi-step reaction with 3 steps 1: iodine / 1 h / 25 °C 2: dihydrogen peroxide; toluene-4-sulfonic acid / acetic acid / 0.42 h / 75 °C 3: sodium carbonate / methanol; water / 20 h / 25 °C View Scheme |
6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol
Idebenone
Conditions | Yield |
---|---|
In methanol; water | 96.9% |
6-(10-hydroxydecyl)-2,3-dimethoxy-5-methylphenol
Idebenone
Conditions | Yield |
---|---|
With oxygen; salcomine In N,N-dimethyl-formamide for 72h; Ambient temperature; | 87% |
With potassium nitrososulfonate In sodium hydroxide for 1h; Ambient temperature; | 67% |
With oxygen; salcomine In N,N-dimethyl-formamide Quantum yield; Ambient temperature; reaction time, additive; |
2,3-dimethoxy-6-methyl-5-benzyloxydecyl-p-benzoquinone
Idebenone
Conditions | Yield |
---|---|
Stage #1: 2,3-dimethoxy-6-methyl-5-benzyloxydecyl-p-benzoquinone With palladium 10% on activated carbon; hydrogen In methanol at 23℃; for 24h; Stage #2: With palladium 10% on activated carbon; oxygen In methanol at 23℃; for 24h; | 82% |
2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone
Idebenone
Conditions | Yield |
---|---|
With sodium carbonate In methanol; water at 25℃; for 20h; | 80% |
With water; sodium carbonate In methanol at 0℃; for 36h; | 61% |
With hydrogenchloride; sodium chloride In methanol |
11-hydroxyundecanoic acid
2,3-Dimethoxy-5-methyl-1,4-benzoquinone
Idebenone
Conditions | Yield |
---|---|
With dihydrogen peroxide; oxygen In water; acetone at 75℃; Catalytic behavior; Reagent/catalyst; Temperature; | 80% |
With dipotassium peroxodisulfate; oxygen; silver nitrate In water; acetonitrile at 80℃; for 4h; Catalytic behavior; Reagent/catalyst; Solvent; | 80% |
With dipotassium peroxodisulfate; silver nitrate In water; acetonitrile at 80℃; for 4h; | 75% |
Stage #1: 11-hydroxyundecanoic acid; 2,3-Dimethoxy-5-methyl-1,4-benzoquinone With silver nitrate In water; acetonitrile Stage #2: With dipotassium peroxodisulfate In water; acetonitrile at 75℃; for 3h; Solvent; Reagent/catalyst; | 65% |
Idebenone
Conditions | Yield |
---|---|
Stage #1: C19H30O5 With dipotassium hydrogenphosphate; potassium hydroxylamine-N,N-disulphonate In N,N-dimethyl-formamide at 50℃; for 8h; Stage #2: With hydrogenchloride In ethanol; N,N-dimethyl-formamide at 50℃; for 8h; Stage #3: With lithium aluminium tetrahydride In N,N-dimethyl-formamide at 80℃; for 3h; | 63% |
2,3-dimethoxy-5-methyl-6-(9'-methoxycarbonylnonyl)-1,4-benzoquinone
Idebenone
Conditions | Yield |
---|---|
(i) LiAlH4, (ii) aq. FeCl3; Multistep reaction; |
Idebenone
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; iron(III) chloride 1.) diethyl ether, RT, 1 h, 2.) diethyl ether; Yield given. Multistep reaction; |
methyl 10-chloro-10-oxodecanoate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 71 percent / AlCl3 / CH2Cl2 / 24 h / Heating 2: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 3: 96 percent / Et3N; DMAP / CH2Cl2 / 7 h / 20 °C 4: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 5: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 6: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 7: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme |
sebacic acid mono methyl ester
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: thionyl chloride 2: 71 percent / AlCl3 / CH2Cl2 / 24 h / Heating 3: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 4: 96 percent / Et3N; DMAP / CH2Cl2 / 7 h / 20 °C 5: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 6: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 7: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 8: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme |
1-(2,3,4,5-tetramethoxy-6-methylphenyl)-1,10-decenediol
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 96 percent / Et3N; DMAP / CH2Cl2 / 7 h / 20 °C 2: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 3: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 4: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 5: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme |
methyl 10-(2,3,4,5-tetramethoxy-6-methylphenyl)-10-undecenoate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 92 percent / LiAlH4 / tetrahydrofuran / 1 h / 0 °C 2: 96 percent / Et3N; DMAP / CH2Cl2 / 7 h / 20 °C 3: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 4: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 5: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 6: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme |
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 2: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 3: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme |
10-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 2: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme |
10-methylcarbonyloxy-1-(2,3,4,5-tetramethoxy-6-methylphenyl)decylacetate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 49 percent / LiBr / dimethylformamide / 24 h / 120 °C 2: 99 percent / H2 / Pd/C / methanol / 1 h / 20 °C 3: 88 percent / CAN / acetonitrile; H2O / 0.25 h / 0 °C 4: 61 percent / Na2CO3; H2O / methanol / 36 h / 0 °C View Scheme |
methyl 10-(2'-hydroxy-3',4'-dimethoxy-6'-methylphenyl)decanoate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 2: 67 percent / ON(SO3K)2 / aq. NaOH / 1 h / Ambient temperature View Scheme |
methyl 9-(2'-hydroxy-3',4'-dimethoxy-6'-methylbenzoyl)nonanoate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) NaBH4, 2.) H2 / 2.) Pd/C 2: LiAlH4 / tetrahydrofuran; diethyl ether / 1 h / Ambient temperature 3: 67 percent / ON(SO3K)2 / aq. NaOH / 1 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 1: potassium dihydrogenphosphate; potassium nitrososulfonate 2: (i) LiAlH4, (ii) aq. FeCl3 View Scheme |
9-bromononan-1-ol
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 9 steps 2: 95 percent / dimethylsulfoxide / 15 h / 80 °C 3: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 4: PCl5 / CH2Cl2 / 2 h / 25 °C 5: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 6: 79 percent / NaOH / methanol / 2 h / Ambient temperature 7: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 8: NaOH / methanol / 24 h / 5 °C 9: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
9-bromononyl acetate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 8 steps 1: 95 percent / dimethylsulfoxide / 15 h / 80 °C 2: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 3: PCl5 / CH2Cl2 / 2 h / 25 °C 4: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 5: 79 percent / NaOH / methanol / 2 h / Ambient temperature 6: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 7: NaOH / methanol / 24 h / 5 °C 8: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
methyl 10-hydroxydecanoate
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 7 steps 1: 1.) NaOH / p-TsOH / 1.) MeOH, reflux, 3 h; 2.) 60 degC, 2 h 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
10-acetoxydecanoic acid
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 6 steps 1: PCl5 / CH2Cl2 / 2 h / 25 °C 2: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 3: 79 percent / NaOH / methanol / 2 h / Ambient temperature 4: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 5: NaOH / methanol / 24 h / 5 °C 6: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
10-acetoxydecanoyl chloride
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 5 steps 1: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 5 steps 1: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 5 steps 1: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 2: 79 percent / NaOH / methanol / 2 h / Ambient temperature 3: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 4: NaOH / methanol / 24 h / 5 °C 5: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 2 steps 1.1: aluminum (III) chloride / dichloromethane / 72 h / 4 °C 1.2: 8 h / 25 °C 2.1: dipotassium hydrogenphosphate; potassium hydroxylamine-N,N-disulphonate / N,N-dimethyl-formamide / 8 h / 50 °C 2.2: 8 h / 50 °C 2.3: 3 h / 80 °C View Scheme |
9-acetoxydecanenitrile
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 44 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: AlCl3 / 1,2-dichloro-ethane / 5 degC, 2 h; 20 degC, 70 h 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme | |
Multi-step reaction with 7 steps 1: 86 percent / NaOH, 3N HCl / ethanol / 19 h / Heating 2: PCl5 / CH2Cl2 / 2 h / 25 °C 3: 29 percent / AlCl3 / 1,2-dichloro-ethane / 72 h / 20 °C 4: 79 percent / NaOH / methanol / 2 h / Ambient temperature 5: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 6: NaOH / methanol / 24 h / 5 °C 7: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
6-(10-hydroxy-1-oxodecyl)-2,3-dimethoxy-5-methylphenol
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 2: NaOH / methanol / 24 h / 5 °C 3: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
6-(10-acetoxydecyl)-2,3-dimethoxy-5-methylphenol
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOH / methanol / 24 h / 5 °C 2: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
Acetic acid 10-(2-hydroxy-3,4-dimethoxy-6-methyl-phenyl)-10-oxo-decyl ester
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 79 percent / NaOH / methanol / 2 h / Ambient temperature 2: H2, 70percent HClO4 / 5percent Pd-C / 24 h / Ambient temperature 3: NaOH / methanol / 24 h / 5 °C 4: O2 / salcomine / dimethylformamide / Ambient temperature; reaction time, additive View Scheme |
9-ethoxycarbonylnonanoic acid chloride
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: (i) AlCl3, (ii) (hydrolysis) 2: hydrogenchloride 3: potassium dihydrogenphosphate; potassium nitrososulfonate 4: (i) LiAlH4, (ii) aq. FeCl3 View Scheme |
3,4,5-trimethoxytoluene
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: nitric acid; potassium bromide / acetic anhydride / 1.25 h / 20 °C 2.1: palladium diacetate; triethylamine; triphenylphosphine / 72 h / 120 °C / Inert atmosphere 2.2: 3 h / 25 °C 3.1: iodine / 1 h / 25 °C 4.1: dihydrogen peroxide; toluene-4-sulfonic acid / acetic acid / 0.42 h / 75 °C 5.1: sodium carbonate / methanol; water / 20 h / 25 °C View Scheme | |
Multi-step reaction with 4 steps 1: (i) AlCl3, (ii) (hydrolysis) 2: hydrogenchloride 3: potassium dihydrogenphosphate; potassium nitrososulfonate 4: (i) LiAlH4, (ii) aq. FeCl3 View Scheme |
9-(2-hydroxy-3,4-dimethoxy-6-methylbenzoyl)nonanoic acid
Idebenone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: hydrogenchloride 2: potassium dihydrogenphosphate; potassium nitrososulfonate 3: (i) LiAlH4, (ii) aq. FeCl3 View Scheme |
nonanoic acid
Idebenone
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux; | 100% |
Idebenone
[bromo(difluoro)methyl](trimethyl)silane
Conditions | Yield |
---|---|
With potassium hydrogen difluoride In dichloromethane; water at 20℃; for 10h; Reagent/catalyst; | 98% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux; | 97.4% |
Idebenone
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 4h; Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With novozym 435 In toluene at 20℃; for 48h; 4A molecular sieves; | 92% |
In ethyl acetate; toluene | 630 mg (92%) |
silica gel In ethyl acetate; toluene | 630 mg (92%) |
Idebenone
methanesulfonyl chloride
10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decyl methanesulfonate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; | 91% |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; | 91% |
With triethylamine In dichloromethane at 10 - 15℃; for 1.5 - 1.75h; |
Idebenone
acetic anhydride
2,3-dimethoxy-5-methyl-6-(10'-acetoxydecyl)-1,4-benzoquinone
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 15h; Ambient temperature; | 90.7% |
In pyridine | |
With pyridine |
1-decanoic acid
Idebenone
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux; | 90.2% |
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux; | 90.2% |
Conditions | Yield |
---|---|
With novozym 435 In toluene at 20℃; for 48h; 4A molecular sieves; | 87% |
Idebenone
Conditions | Yield |
---|---|
With 1,2-Diiodoethane; tetra-(n-butyl)ammonium iodide; Diphenylvinylphosphine In N,N-dimethyl-formamide; acetonitrile at 80℃; for 0.25h; Inert atmosphere; Sealed tube; | 86% |
Idebenone
10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decanal
Conditions | Yield |
---|---|
Stage #1: Idebenone With oxalyl dichloride; dimethyl sulfoxide In dichloromethane for 0.166667h; Stage #2: With triethylamine In dichloromethane for 1h; | 84% |
With oxalyl dichloride; triethylamine In dichloromethane; dimethyl sulfoxide at -78℃; for 1.5h; | 84% |
With sodium acetate; pyridinium chlorochromate In dichloromethane for 2.5h; Ambient temperature; | 38.7% |
With Dess-Martin periodane In dichloromethane at 0℃; for 4h; Inert atmosphere; |
Idebenone
10-(2,3-Dimethoxy-5-methyl-1,4-benzoquinon-6-yl)decanoic acid
Conditions | Yield |
---|---|
With Jones reagent In acetone | 83% |
With phosphate buffer; D-glucose; rat liver slices at 37℃; for 1h; incubation, pH=7.4; | |
With Jones reagent In acetone at 0℃; for 0.333333h; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; for 3h; Inert atmosphere; Cooling with ice; | 83% |
Idebenone
trolox
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In acetonitrile at 0 - 20℃; for 1.5h; Inert atmosphere; | 82% |
Idebenone
Conditions | Yield |
---|---|
With tetrabutylammonium tetra(tert-butyl alcohol) coordinate fluoride; N-tosyl-4-chlorobenzenesulfonimidoyl fluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 20℃; for 0.5h; Sealed tube; | 82% |
lauric acid
Idebenone
Conditions | Yield |
---|---|
With dicyclohexyl-carbodiimide In tetrahydrofuran for 24h; Reflux; | 81.1% |
Idebenone
trimethyl(pentafluoroethyl)silane
Conditions | Yield |
---|---|
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; lithium trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Inert atmosphere; | 80% |
di-tert-butyl dicarbonate
Idebenone
di-tert-butyl 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl-1,4-phenylene dicarbonate
Conditions | Yield |
---|---|
With triethylamine In tetrahydrofuran at 0 - 20℃; | 79% |
Conditions | Yield |
---|---|
With sulfuric acid In cyclohexane at 25 - 65℃; Reflux; | 78% |
Idebenone
Conditions | Yield |
---|---|
With lithium tetrafluoroborate In dichloromethane at 30℃; for 1h; | 77% |
Idebenone
tetramethylammonium trifluoromethylselenate(0)
Conditions | Yield |
---|---|
With calcium chloride In acetonitrile at 60℃; Temperature; Inert atmosphere; Sealed tube; Glovebox; | 77% |
Idebenone
10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dienyl)decyl nitrate
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; tetrabutylammonium nitrate In dichloromethane at -70℃; for 2h; | 75% |
With 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; tetrabutylammonium nitrate In dichloromethane at -70℃; for 2h; | 75% |
Multi-step reaction with 2 steps 1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C 2: tetrabutylammonium nitrate; sodium nitrate / acetic acid butyl ester; acetonitrile / 18 h / 80 °C View Scheme | |
Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 16 h / 0 - 20 °C 2: sodium nitrate; tetrabutylammonium nitrate / acetic acid butyl ester; acetonitrile / 18 h / 80 °C View Scheme |
Idebenone
(trifluoromethyl)trimethylsilane
Conditions | Yield |
---|---|
With potassium fluoride; 2-fluoropyridine; silver trifluoromethanesulfonate; Selectfluor In ethyl acetate at 20℃; for 12h; Glovebox; Inert atmosphere; | 64% |
The Molecular Structure of Idebenone (CAS NO.58186-27-9):
Empirical Formula: C19H30O5
Molecular Weight: 338.4385
IUPAC Name: 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
Appearance: Yellow-Orange Crystalline Solid
Nominal Mass: 338 Da
Average Mass: 338.4385 Da
Monoisotopic Mass: 338.209324 Da
Index of Refraction: 1.502
Molar Refractivity: 92.13 cm3
Molar Volume: 312 cm3
Surface Tension: 41 dyne/cm
Density: 1.08 g/cm3
Flash Point: 170.1 °C
Enthalpy of Vaporization: 88.13 kJ/mol
Boiling Point: 497.3 °C at 760 mmHg
Melting Point: 52-550 °C
Vapour Pressure: 5.67E-12 mmHg at 25°C
Storage temp: Room temp
Product Categories: Anthraquinones, Hydroquinones and Quinones;Cnbio;Intermediates & Fine Chemicals;Pharmaceuticals
InChI
InChI=1/C19H30O5/c1-14-15(12-10-8-6-4-5-7-9-11-13-20)17(22)19(24-3)18(23-2)16(14)21/h20H,4-13H2,1-3H3
Smiles
C1(=C(C(C(C)=C(C1=O)CCCCCCCCCCO)=O)OC)OC
On July 23, 2008, Health Canada issued a Notice of Compliance under the Notice of Compliance with Conditions (NOC/c) Policy to Santhera Pharmaceuticals (Switzerland) Ltd. for the drug product Catena. The product was authorized under the NOC/c Policy on the basis of the promising nature of the clinical evidence, and the need for a confirmatory study to verify its clinical benefit. Patients should be advised of the fact that the market authorization was issued with conditions.
Idebenone (CAS NO.58186-27-9) is a synthetic analogue of coenzyme Q10 used in Europe in the treatment of vascular and degenerative diseases of the central nervous system. It has been used in the treatment of Friedreich's ataxia and also in topical applications to treat wrinkles.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mammal (species unspecified) | LD50 | unreported | > 1gm/kg (1000mg/kg) | Chemical and Pharmaceutical Bulletin. Vol. 39, Pg. 367, 1991. | |
mouse | LD50 | intraperitoneal | 757mg/kg (757mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985. |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985. | |
mouse | LD50 | subcutaneous | > 10gm/kg (10000mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985. | |
rat | LD50 | intraperitoneal | 830mg/kg (830mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985. |
rat | LD50 | oral | 10gm/kg (10000mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985. |
rat | LD50 | subcutaneous | > 10gm/kg (10000mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 13, Pg. 3931, 1985. |
Although studies in animals have shown no harmful effects, this product should not be taken during the first three months of pregnancy and during nursing, only when absolutely necessary and always under a doctor's supervision.
Hazard Codes: Xi
RTECS: GU5290000
Idebenone (CAS NO.58186-27-9) is also called as Idebenone [INN:JAN] ; 6-(10-Hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone ; Idebenona ; Idebenona [Spanish] ; Idebenone ; Idebenonum ; Idebenonum [Latin] ; 2,5-Cyclohexadiene-1,4-dione, 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methyl- ; 2,5-Cyclohexadiene-1,4-dione, 5,6-dimethoxy-2-(10-hydroxydecyl)-3-methyl- ; 2-(10-Hydroxydecyl)-5,6-dimethoxy-3-methyl-p-benzoquinone .It is an organic compound of the quinone family and promoted commercially as a synthetic analog of coenzyme Q10 (CoQ10).
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