(1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

Base Information

• Chemical Name: (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one
• CAS No.: 128261-67-6
• Molecular Formula: C₁₆H₁₈O₃S
• Molecular Weight: 290.383
• Mol file: 128261-67-6.mol

Synonyms:(1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

Chemical Property of (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one

There total 9 articles about (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-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: 93.0%

(1R,5S)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one (128261-66-5) → (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one (128261-67-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

Reference yield:

(1R,5S)-(+)-nopinone (38651-65-9) → (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one (128261-67-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) lithium diisopropylamide / 1) THF, hexane, -78 deg C, 30 min, 0 deg C, 30 min, 2) -78 deg C, 20 min, to r.t., 5 h, r.t., 15 h

2: m-CPBA / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 10 h

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

4: 93 percent / CuBr*Me₂S / tetrahydrofuran / 7 h

5: m-CPBA / CH₂Cl₂ / 1) 0 deg C, 1h, 2) r.t., 10 h

6: Ac₂O, methanesulfonic acid / CH₂Cl₂ / 1) 0 deg C, 1 h, 2) r.t., 15 h

7: 93 percent / m-CPBA / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) r.t., 2 h

With copper(I) bromide dimethylsulfide complex; methanesulfonic acid; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00025a023

Reference yield:

(1R,5R)-6,6-Dimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one (128261-64-3) → (1R,5S)-4,6,6-Trimethyl-3-(phenylsulfonyl)bicyclo<3.1.1>hept-3-en-2-one (128261-67-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / CuBr*Me₂S / tetrahydrofuran / 7 h

2: m-CPBA / CH₂Cl₂ / 1) 0 deg C, 1h, 2) r.t., 10 h

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

4: 93 percent / m-CPBA / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) r.t., 2 h

With copper(I) bromide dimethylsulfide complex; methanesulfonic acid; acetic anhydride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00025a023

upstream raw materials:

(1R,5S)-4,6,6-trimethyl-3-(phenylthio)bicyclo<3.1.1>hept-3-en-2-one

(1R,5S)-(+)-nopinone

beta-pinene

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

Downstream raw materials:

(4S)-trans-β-elemenone

(4S,5S)-2-(1-Hydroxy-1-methyl-ethyl)-4-isopropenyl-5-methyl-5-vinyl-cyclohexanone

(4S,5S)-1-acetoxy-4-isopropenyl-5-methyl-5-vinyl-1-cyclohexene

Acetic acid (4S,5R)-5-but-3-enyl-4-isopropenyl-5-methyl-cyclohex-1-enyl ester