1-Cyclopentacycloundecenol,1,2,3,3a,4,7,8,11,12,12a-decahydro-3a,6,10-trimethyl-1-(1-methylethenyl)-,(1S,3aS,5E,9E,12aS)-

Base Information

Chemical Name:1-Cyclopentacycloundecenol,1,2,3,3a,4,7,8,11,12,12a-decahydro-3a,6,10-trimethyl-1-(1-methylethenyl)-,(1S,3aS,5E,9E,12aS)-
CAS No.:163252-97-9
Molecular Formula:C₂₀H₃₂O
Molecular Weight:288.473
Hs Code.:
Mol file:163252-97-9.mol

Synonyms:1-Cyclopentacycloundecenol,1,2,3,3a,4,7,8,11,12,12a-decahydro-3a,6,10-trimethyl-1-(1-methylethenyl)-,(1R*,3aR*,5E,9E,12aR*)-(-)-; (-)-Isoedunol; Isoedunol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 1-Cyclopentacycloundecenol,1,2,3,3a,4,7,8,11,12,12a-decahydro-3a,6,10-trimethyl-1-(1-methylethenyl)-,(1S,3aS,5E,9E,12aS)-

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MSDS Files:: SDS file from LookChem

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Technology Process of 1-Cyclopentacycloundecenol,1,2,3,3a,4,7,8,11,12,12a-decahydro-3a,6,10-trimethyl-1-(1-methylethenyl)-,(1S,3aS,5E,9E,12aS)-

There total 16 articles about 1-Cyclopentacycloundecenol,1,2,3,3a,4,7,8,11,12,12a-decahydro-3a,6,10-trimethyl-1-(1-methylethenyl)-,(1S,3aS,5E,9E,12aS)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

: 868784-12-7
(5E,9E)-(3aS,12aS)-3a,6,10-Trimethyl-3,3a,4,7,8,11,12,12a-octahydro-2H-cyclopentacycloundecen-1-one

: 6386-71-6
isopropenyllithium

: 163252-97-9,163135-89-5
isoedunol

Guidance literature:: In diethyl ether; pentane; at -10 ℃; for 0.5h;
DOI:10.1021/ja055137+

Reference yield:

: 5-((3E,7E)-9-Iodo-3,7-dimethyl-nona-3,7-dienyl)-2,2,4,4-tetramethyl-[1,3]dioxolane

: 163252-97-9,163135-89-5
isoedunol

Guidance literature:: Multi-step reaction with 12 steps

1.1: LDA / tetrahydrofuran; hexane / 0.17 h / -90 °C

1.2: 1.96 g / tetrahydrofuran; hexane / 8 h / -78 °C

2.1: 96 percent / NaOMe / 0.5 h / 50 °C

3.1: 99 percent / acetic anhydride / 24 h / 23 °C

4.1: 60 percent / ClTi(Oi-Pr)3 / tetrahydrofuran / 48 h / 0 - 23 °C

5.1: 90 percent / trimethylaluminum / CH₂Cl₂; toluene / 72 h / -10 - 4 °C

6.1: aq. AcOH / 3 h / 55 °C

7.1: 236 mg / aq. NaIO₄; AcOH / 0.5 h / 23 °C

8.1: SmI₂ / tetrahydrofuran / 67 °C

9.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / 26 h / -78 - 4 °C

10.1: 137 mg / lithium aluminum hydride / tetrahydrofuran / 67 °C

11.1: 98 percent / methanesulfonyl chloride; Et₃N / CH₂Cl₂ / 73 h / -30 - 4 °C

12.1: 82 percent / pentane; diethyl ether / 0.5 h / -10 °C

With triisopropoxytitanium(IV) chloride; sodium periodate; lithium aluminium tetrahydride; samarium diiodide; oxalyl dichloride; trimethylaluminum; sodium methylate; acetic anhydride; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; 4.1: Kulinkovich reaction / 9.1: Swern oxidation;
DOI:10.1021/ja055137+

Reference yield:

: 63730-35-8
(2E,6E)-3,7-Dimethyl-9-(2,2,5,5-tetramethyl-[1,3]dioxolan-4-yl)-nona-2,6-dien-1-ol

: 163252-97-9,163135-89-5
isoedunol

Guidance literature:: Multi-step reaction with 14 steps

1.1: Et₃N / benzene; pentane / 1.5 h / 0 °C

2.1: LiI / tetrahydrofuran / 0.5 h / 0 °C

3.1: LDA / tetrahydrofuran; hexane / 0.17 h / -90 °C

3.2: 1.96 g / tetrahydrofuran; hexane / 8 h / -78 °C

4.1: 96 percent / NaOMe / 0.5 h / 50 °C

5.1: 99 percent / acetic anhydride / 24 h / 23 °C

6.1: 60 percent / ClTi(Oi-Pr)3 / tetrahydrofuran / 48 h / 0 - 23 °C

7.1: 90 percent / trimethylaluminum / CH₂Cl₂; toluene / 72 h / -10 - 4 °C

8.1: aq. AcOH / 3 h / 55 °C

9.1: 236 mg / aq. NaIO₄; AcOH / 0.5 h / 23 °C

10.1: SmI₂ / tetrahydrofuran / 67 °C

11.1: oxalyl chloride; Et₃N; DMSO / CH₂Cl₂ / 26 h / -78 - 4 °C

12.1: 137 mg / lithium aluminum hydride / tetrahydrofuran / 67 °C

13.1: 98 percent / methanesulfonyl chloride; Et₃N / CH₂Cl₂ / 73 h / -30 - 4 °C

14.1: 82 percent / pentane; diethyl ether / 0.5 h / -10 °C

With triisopropoxytitanium(IV) chloride; sodium periodate; lithium aluminium tetrahydride; samarium diiodide; oxalyl dichloride; trimethylaluminum; sodium methylate; acetic anhydride; acetic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; lithium iodide; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; benzene; 6.1: Kulinkovich reaction / 11.1: Swern oxidation;
DOI:10.1021/ja055137+