1H-Benzocyclohepten-7-ol,2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-, (4aR,7S)-rel-

Base Information

• Chemical Name: 1H-Benzocyclohepten-7-ol,2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-, (4aR,7S)-rel-
• CAS No.: 25490-91-9
• Molecular Formula: C₁₅H₂₆O
• Molecular Weight: 222.371
• Mol file: 25490-91-9.mol

Synonyms:1H-Benzocyclohepten-7-ol,2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-, trans-;1H-Benzocyclohepten-7-ol, 2,3,4,4a,5,6,7,8-octahydro-1,1,4aa,7a-tetramethyl- (7CI,8CI); (+)-Epiwiddrol; Epiwiddrol

Chemical Property of 1H-Benzocyclohepten-7-ol,2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-, (4aR,7S)-rel-

Chemical Property:

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Technology Process of 1H-Benzocyclohepten-7-ol,2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-, (4aR,7S)-rel-

There total 62 articles about 1H-Benzocyclohepten-7-ol,2,3,4,4a,5,6,7,8-octahydro-1,1,4a,7-tetramethyl-, (4aR,7S)-rel- 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: 96.0%

Acetic acid (4aR,7R)-1,1,4a,7-tetramethyl-2,3,4,4a,5,6,7,8-octahydro-1H-benzocyclohepten-7-yl ester (70069-94-2,107381-12-4) → (+/-)-widdrol (6892-80-4,25490-91-9,75196-99-5,97232-48-9,116949-90-7,141724-17-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 0.5h;

DOI:10.1016/S0040-4020(01)87741-3

Reference yield: 78.0%

<4aR*,7S*,8R*>-7,8-epoxy-2,3,4,4a,5,6,7,8,-octahydro-1,1,4a,7-tetramethyl-1H-benzocycloheptene (116914-10-4) → (+/-)-epi-widdrol (6892-80-4,25490-91-9,75196-99-5,97232-48-9,116949-90-7,141724-17-6)

Guidance literature:

With lithium aluminium tetrahydride; In 1,2-dimethoxyethane; for 6h; Ambient temperature;

DOI:10.1016/S0040-4020(01)87742-5

Reference yield:

(5aS,9aR)-5a,9,9-Trimethyl-9a-vinyl-octahydro-benzo[b]oxepin-2-one (75154-34-6) → (+/-)-widdrol (6892-80-4,25490-91-9,75196-99-5,97232-48-9,116949-90-7,141724-17-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 81 percent / lithium diisopropylamide / tetrahydrofuran / -78 °C

2: lithium diisopropylamide / hexamethylphosphoric acid triamide; tetrahydrofuran

3: 2.) tetra-n-butylammonium fluoride / 1.) toluene, 11o deg C, 10 h

4: 1.) SOCl₂, 2.) MCPBA, 3.) LAH

With lithium aluminium tetrahydride; thionyl chloride; tetrabutyl ammonium fluoride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/ja00542a059

upstream raw materials:

Widdrol-epoxid

cobalt(III) acetate

thujopsene

(1aR,2S,4aS,8aS)-2-Chloro-2,4a,8,8-tetramethyl-decahydro-cyclopropa[d]naphthalene

Downstream raw materials:

1,1,3-Trimethyl-3-(3,5-dihydroxy-3-methyl-pentyl)-cyclohexanol-⁽²⁾

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