(2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-one

Base Information

• Chemical Name: (2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-one
• CAS No.: 61431-50-3
• Molecular Formula: C₁₄H₂₂O
• Molecular Weight: 206.328
• Mol file: 61431-50-3.mol

Synonyms:

Chemical Property of (2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-one

There total 17 articles about (2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-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:

(3S,3aS,7aS)-3,3a,6-Trimethyl-3-[4-(tetrahydro-pyran-2-yloxy)-butyl]-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one (61431-49-0) → (2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-one (61431-50-3)

Guidance literature:

Multistep reaction;

Reference yield:

2,5-dimethylcyclohexanone (932-51-4) → (2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-one (61431-50-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.) 1,2-dimethoxyethane , Ethanol heat for 14.5 h; 2.) 15 min,0 deg C

2: 1.) O₃; 2.) Zn,50percentHOAc / 1.) CH₂Cl₂,- 78 deg C; 2.) reflux

3: 79 percent / Jones reagent / acetone

4: 95 percent / K₂CO₃ / acetone / 2 h / Heating

5: 97 percent / Br₂ / acetic acid; acetic acid / 6.5 h

6: 91 percent / CaCO₃ / N,N-dimethyl-acetamide / 0.75 h / Heating

7: 95 percent / KOH / H₂O; ethanol / 15.5 h / Ambient temperature

8: 1.) Diisobutylaluminum hydride; 2.) 20percentH₂SO₄ / 1.) CH₂Cl₂, 0 deg C,benzene,15 min.; 45 min.at room temp.,2.) 30 min., 0 deg C

10: LDA

11: 100 percent / p-TsOH / methanol / 24 h / Ambient temperature

With potassium hydroxide; jones reagent; sulfuric acid; bromine; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; ozone; acetic acid; calcium carbonate; zinc; lithium diisopropyl amide; In methanol; ethanol; N,N-dimethyl acetamide; water; acetic acid; acetone;

DOI:10.1021/jo01309a003

Reference yield:

(3a-cis)-3a,4,5,7a-Tetrahydro-3a,6-dimethyl-2(3H)-benzofuranone (33722-72-4) → (2RS,1'SR,4'SR)-2-(1',4'-dimethylcyclohex-2'-enyl)-2-methylcyclopentan-1-one (61431-50-3)

Guidance literature:

Multi-step reaction with 4 steps

2: LDA

3: 100 percent / p-TsOH / methanol / 24 h / Ambient temperature

With toluene-4-sulfonic acid; lithium diisopropyl amide; In methanol;

DOI:10.1021/jo01309a003

upstream raw materials:

(3α,3aα,7aα)-3a,4,5,7a-Tetrahydro-3,3a,6-trimethyl-3-(4-hydroxybutyl)-2(3H)-benzofuranone

(3S,3aS,7aS)-3,3a,6-Trimethyl-3-[4-(tetrahydro-pyran-2-yloxy)-butyl]-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one

2,5-dimethylcyclohexanone

(3a-cis)-3a,4,5,7a-Tetrahydro-3a,6-dimethyl-2(3H)-benzofuranone