(S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone

Base Information

Chemical Name:(S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone
CAS No.:455252-82-1
Molecular Formula:C₂₀H₃₂O₂
Molecular Weight:304.473
Hs Code.:

Synonyms:(S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone

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Chemical Property of (S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone

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Technology Process of (S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone

There total 10 articles about (S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone 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: 90.0%

: 455252-81-0
(S)-4-{2-[(1S,2S,4S,5S)-4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl]-ethyl}-2,4-dimethyl-cyclohex-2-enone

: 455252-82-1
(S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone

Guidance literature:: With toluene-4-sulfonic acid; In methanol; at 25 ℃; for 3h;
DOI:10.1016/S0040-4039(02)00729-3

Reference yield:

: 80-57-9,1196-01-6
(-)-Verbenone

: 455252-82-1
(S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / CuI

2.1: LiAlH₄ / tetrahydrofuran / -78 °C

3.1: imidazole / dimethylformamide

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 60 percent / Me₂S

5.1: 56 percent / Dess-Martin periodinane

6.1: 93 percent / n-BuLi / tetrahydrofuran / -78 °C

7.1: O₃; Me₂S / CH₂Cl₂ / -78 °C

7.2: KOH / methanol

8.1: 90 percent / p-toluenesiulfonic acid / methanol / 3 h / 25 °C

With 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)00729-3

Reference yield:

: 55314-73-3
(S)-citronellyl magnesium bromide

: 455252-82-1
(S)-4-[2-((1S,2S,4S,5S)-4-Hydroxy-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-ethyl]-2,4-dimethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / CuI

2.1: LiAlH₄ / tetrahydrofuran / -78 °C

3.1: imidazole / dimethylformamide

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 60 percent / Me₂S

5.1: 56 percent / Dess-Martin periodinane

6.1: 93 percent / n-BuLi / tetrahydrofuran / -78 °C

7.1: O₃; Me₂S / CH₂Cl₂ / -78 °C

7.2: KOH / methanol

8.1: 90 percent / p-toluenesiulfonic acid / methanol / 3 h / 25 °C

With 1H-imidazole; copper(l) iodide; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(02)00729-3