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

Base Information

• Chemical Name: (1'R,2'R)-2'-Hydroxycyclohexyl cyclopentene-1-carboxylate
• CAS No.: 141753-26-6
• Molecular Formula: C₁₂H₁₈O₃
• Molecular Weight: 210.273
• Mol file: 141753-26-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (1'R,2'R)-2'-Hydroxycyclohexyl cyclopentene-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: 68.0%

(1R,2R)-trans-1,2-cyclohexanediol (1072-86-2,1460-57-7,1792-81-0,54383-22-1,57794-08-8,931-17-9) + cyclopent-1-enecarbonyl chloride (59253-90-6) → (1'R,2'R)-2'-Hydroxycyclohexyl cyclopentene-1-carboxylate (141753-26-6)

Guidance literature:

With pyridine; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1021/jo00041a046

Reference yield:

n-butyllithium (109-72-8,29786-93-4) + (1'R,2'R)-2'-Hydroxycyclohexyl cyclopentene-1-carboxylate (141753-26-6) → (1S,2S,1'R,2'R)-2'-Hydroxycyclohexyl 2-butylcyclopentane-1-carboxylate (131233-22-2) + (1R,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-butylcyclopentane-1-carboxylate (131139-99-6) + (1S,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-butylcyclopentane-1-carboxylate (141846-03-9) + (1R,2S,1'R,2'R)-2'-Hydroxycyclohexyl 2-butylcyclopentane-1-carboxylate (141846-04-0)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) hexane, diethyl ether, -50 deg C, 10 min, 2.) -50 deg C, 30 min;

DOI:10.1021/jo00041a046

Reference yield:

phenyllithium (591-51-5) + (1'R,2'R)-2'-Hydroxycyclohexyl cyclopentene-1-carboxylate (141753-26-6) → (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) + (1R,2S,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate (141846-02-8) + (1S,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-phenylcyclopentane-1-carboxylate (141846-01-7)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) cyclohexane, diethyl ether, 0 deg C, 10 min, 2.) -30 deg C, 30 min;

DOI:10.1021/jo00041a046

upstream raw materials:

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

cyclopent-1-enecarbonyl chloride

Downstream raw materials:

(1S,2S,1'R,2'R)-2'-Hydroxycyclohexyl 2-butylcyclopentane-1-carboxylate

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

(1S,2R,1'R,2'R)-2'-Hydroxycyclohexyl 2-butylcyclopentane-1-carboxylate

(1R,2S,1'R,2'R)-2'-Hydroxycyclohexyl 2-butylcyclopentane-1-carboxylate