(1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate

Base Information

• Chemical Name: (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate
• CAS No.: 131139-97-4
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.387
• Mol file: 131139-97-4.mol

Synonyms:(1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate

Chemical Property of (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate

There total 5 articles about (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate 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: 44.0%

lithium diphenylcuprate (23402-69-9) + (1'R,2'R)-2'-Hydroxycyclohexyl (E)-6-chloro-2-hexenoate (131140-05-1) → (1S,2S,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate (131233-20-0) + (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate (131139-97-4)

Guidance literature:

In diethyl ether; at 0 ℃; other esters, various organocuprate compounds;

DOI:10.1016/S0040-4039(00)97723-2

Reference yield:

(1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) → (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate (131139-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) CuBr*Me₂S / 1.) cyclohexane, diethyl ether, 0 deg C, 10 min, 2.) 0 deg C, 30 min

With pyridine; copper(I) bromide dimethylsulfide complex; In dichloromethane;

DOI:10.1021/jo00041a046

Reference yield:

(E)-6-chloro-2-hexenoyl chloride (107408-77-5) → (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate (131139-97-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1.) CuBr*Me₂S / 1.) cyclohexane, diethyl ether, 0 deg C, 10 min, 2.) 0 deg C, 30 min

With pyridine; copper(I) bromide dimethylsulfide complex; In dichloromethane;

DOI:10.1021/jo00041a046

upstream raw materials:

lithium diphenylcuprate

(1'R,2'R)-2'-Hydroxycyclohexyl (E)-6-chloro-2-hexenoate

phenyllithium

(1'R,2'R)-2'-Hydroxycyclohexyl cyclopentene-1-carboxylate

Downstream raw materials:

(1R,2R)-(-)-1-formyl-2-phenylcyclopentane

(1R,2R)-trans-2-phenylcyclopentanemethanol