(3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone

Base Information

• Chemical Name: (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone
• CAS No.: 439919-24-1
• Molecular Formula: C₂₀H₂₆O₃
• Molecular Weight: 314.425
• Mol file: 439919-24-1.mol

Synonyms:(3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone

Chemical Property of (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone

There total 5 articles about (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone 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: 95.0%

(1'S,3'S,5'R)-5,5-dimethyl-3'-(3-cyclopentyloxy-4-methoxyphenyl)spiro[1,3-dioxine-2,7'-bicyclo[3.3.0]octane] (439919-23-0) → (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone (439919-24-1)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2004.07.040

Reference yield:

(1'SR,5'RS)-5,5-dimethyl-3'-(3-cyclopentyloxy-4-methoxyphenyl)spiro[1,3-dioxine-2,7'-bicyclo[3.3.0]octan-2'-en] → (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone (439919-24-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / dioxane / 3 h / atmospheric pressure

2: 95 percent / TsOH*H₂O / acetone / 24 h / 20 °C

With hydrogen; toluene-4-sulfonic acid; palladium on activated charcoal; In 1,4-dioxane; acetone;

DOI:10.1016/j.bmc.2004.07.040

Reference yield:

C25H36O5 → (3aR,6aS)-5-[3-(cyclopentyloxy)-4-methoxyphenyl]hexahydro-2(1H)-pentalenone (439919-24-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.99 g / MsCl; Et₃N / CH₂Cl₂ / 24 h / 20 °C

2: 100 percent / H₂ / Pd/C / dioxane / 3 h / atmospheric pressure

3: 95 percent / TsOH*H₂O / acetone / 24 h / 20 °C

With hydrogen; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; palladium on activated charcoal; In 1,4-dioxane; dichloromethane; acetone;

DOI:10.1016/j.bmc.2004.07.040

upstream raw materials:

(1'S,3'S,5'R)-5,5-dimethyl-3'-(3-cyclopentyloxy-4-methoxyphenyl)spiro[1,3-dioxine-2,7'-bicyclo[3.3.0]octane]

(3a'R,6a'S)-5,5-dimethyltetrahydro-1'H-spiro[1,3-dioxane-2,2'-pentalen]-5'(3'H)-one

4-bromo-2-cyclopentyloxyanisole

Downstream raw materials:

(2R,3aS,5S,6aR)-5-(3-Cyclopentyloxy-4-methoxy-phenyl)-octahydro-pentalene-2-carboxylic acid