cis-(1R,4S)-4--2-cyclohexenol

Base Information

• Chemical Name: cis-(1R,4S)-4--2-cyclohexenol
• CAS No.: 147852-44-6
• Molecular Formula: C₁₁H₁₆O₅
• Molecular Weight: 228.245
• Mol file: 147852-44-6.mol

Synonyms:cis-(1R,4S)-4--2-cyclohexenol

Chemical Property of cis-(1R,4S)-4--2-cyclohexenol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-(1R,4S)-4--2-cyclohexenol

There total 4 articles about cis-(1R,4S)-4--2-cyclohexenol 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: 74.0%

3,4-epoxycyclohexene (6705-51-7) + malonic acid dimethyl ester (108-59-8) → 2-((1S,4R)-4-Hydroxy-cyclohex-2-enyl)-malonic acid dimethyl ester (79193-67-2,95590-28-6,114327-01-4,147852-44-6)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾;

DOI:10.1021/ja00409a082

Reference yield:

dimethyl malonate sodium salt (18424-76-5) → 2-((1S,4R)-4-Hydroxy-cyclohex-2-enyl)-malonic acid dimethyl ester (79193-67-2,95590-28-6,114327-01-4,147852-44-6) + (3S,3aS,7aS)-2-Oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-carboxylic acid methyl ester

Guidance literature:

With ammonium cerium(IV) nitrate; sodium acetate; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 20 deg C; 2.) wet acetone;

DOI:10.1021/ja00318a072

Reference yield:

dimethyl malonate sodium salt (18424-76-5) → 2-((1S,4R)-4-Hydroxy-cyclohex-2-enyl)-malonic acid dimethyl ester (79193-67-2,95590-28-6,114327-01-4,147852-44-6) + (3S,3aS,7aS)-2-Oxo-2,3,3a,4,5,7a-hexahydro-benzofuran-3-carboxylic acid methyl ester

Guidance literature:

With ammonium cerium(IV) nitrate; sodium acetate; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, 20 deg C; 2.) wet acetone;

DOI:10.1021/ja00318a072

upstream raw materials:

3,4-epoxycyclohexene

malonic acid dimethyl ester

dimethyl malonate sodium salt

acetic acid (1S,4R)-(-)-4-hydroxycyclohex-2-enyl ester

Downstream raw materials:

(S)-4-[bis(methoxycarbonyl)methyl]-2-cyclohexen-1-one

dimethylcyclohexa-2,4-dienylmalonate

(R)-2-(2,4-Cyclohexadienyl)acetic acid methyl ester

(-)-(R)-2,4-cyclohexadiene-1-acetic acid