(1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one

Base Information

Chemical Name:(1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one
CAS No.:139339-24-5
Molecular Formula:C₂₂H₂₈O₃S
Molecular Weight:372.529
Hs Code.:

Synonyms:(1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one

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Chemical Property of (1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one

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Technology Process of (1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one

There total 6 articles about (1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one 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: 50.0%

: 139339-12-1
(1R,5S)-4-ethyl-6,6-dimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

: 870-63-3
prenyl bromide

: 139339-24-5
(1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one

: 139339-18-7
(1R,5S)-6,6-Dimethyl-4-<(1R)-1,4-dimethyl-3-pentenyl>-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

: 139339-21-2
(1R,5S)-6,6-Dimethyl-4-<(1S)-1,4-dimethyl-3-pentenyl>-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

: (1R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-2-en-2-yl 3-methyl-2-butenyl ether

Guidance literature:: With potassium carbonate; In acetonitrile; at 50 ℃; for 5h;
DOI:10.1021/jo00071a025

Reference yield: 16.0%

: 139339-12-1
(1R,5S)-4-ethyl-6,6-dimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

: 870-63-3
prenyl bromide

: 139339-24-5
(1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one

: 139339-18-7
(1R,5S)-6,6-Dimethyl-4-<(1R)-1,4-dimethyl-3-pentenyl>-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

: 139339-21-2
(1R,5S)-6,6-Dimethyl-4-<(1S)-1,4-dimethyl-3-pentenyl>-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

Guidance literature:: With potassium carbonate; In acetonitrile; at 50 ℃; Yields of byproduct given;
DOI:10.1016/0040-4039(91)80128-S

Reference yield:

: 128261-64-3
(1R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one

: 139339-24-5
(1R,3R,5S)-4-<(E)-Ethylidene>-6,6-dimethyl-3-(3-methyl-2-butenyl)-3-(phenylsulfonyl)bicyclo<3.1.1>heptan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 76 percent / CuI / tetrahydrofuran / 1 h / -50 - -40 °C

2: m-CPBA / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 30 min

3: MsOH, Ac₂O / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) r.t., 15 h

4: 80 percent / m-CPBA / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) r.t., 2 h

5: 16 percent / K₂CO₃ / acetonitrile / 5 h / 50 °C

With methanesulfonic acid; acetic anhydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; copper(l) iodide; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo00071a025