<1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one

Base Information

• Chemical Name: <1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one
• CAS No.: 96759-74-9
• Molecular Formula: C₁₆H₂₀OS
• Molecular Weight: 260.4
• Mol file: 96759-74-9.mol

Synonyms:<1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one

Chemical Property of <1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one

There total 5 articles about <1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-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:

2-methyl-2-cyclopenten-1-one (1120-73-6) → <1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one (96759-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) Zn / 1.) -78 deg C; 2.) AcOH, RT

2: H₂O, TiCl₄ / acetic acid / 0.25 h / Ambient temperature

With water; titanium tetrachloride; zinc; In acetic acid;

DOI:10.1021/ja00299a061

Reference yield:

(R)-(+)-allyl p-tolyl sulphoxide (89708-79-2) → <1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one (96759-74-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) Zn / 1.) -78 deg C; 2.) AcOH, RT

2: H₂O, TiCl₄ / acetic acid / 0.25 h / Ambient temperature

With water; titanium tetrachloride; zinc; In acetic acid;

DOI:10.1021/ja00299a061

Reference yield:

Acetic acid (S)-2-methyl-3-((E)-3-p-tolylsulfanyl-allyl)-cyclopent-1-enyl ester (110366-53-5) → <1(R),5(S),8(S))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one (96759-75-0) + <1(R),5(S),8(R))>-1-methyl-8-(p-tolylthio)-cis-bicyclo<3.3.0>octan-2-one (96759-74-9)

Guidance literature:

With titanium tetrachloride; acetic acid; for 0.333333h; Yield given. Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo00381a002

upstream raw materials:

Acetic acid (S)-2-methyl-3-((E)-3-p-tolylsulfanyl-allyl)-cyclopent-1-enyl ester

2-methyl-2-cyclopenten-1-one

(R)-(+)-allyl p-tolyl sulphoxide

<3(S),S(R)>-1-acetoxy-2-methyl-3-<(E)-3-(p-tolylsulfinyl)-2-propen-1-yl>-1-cyclopentene

Downstream raw materials:

(1S,3aS,6R,6aR)-6a-Methyl-6-p-tolylsulfanyl-octahydro-pentalen-1-ol

(3aS,6R,6aS)-(3aα,6aα)-2,3,3a,5,6,6a-hexahydro-6α-<2,2-dimethyl-3-(tosyloxy)propyl>-1,4-pentalenedione ethylene ketal

(3aR,6aS)-(3aα,6aα)-hexahydro-6a-methyl-6-(p-tolylsulfinyl)-1(2H)-pentalenone ethylene ketal

(1R,3aR,6aS)-(3aα,6aα)-octahydro-1-bromo-6a-methyl-6-methylene-1-(p-tolylsulfinyl)pentalene