cis-(1S,4R)-1-Acetoxy-4--2-cyclohexene

Base Information

• Chemical Name: cis-(1S,4R)-1-Acetoxy-4--2-cyclohexene
• CAS No.: 147852-45-7
• Molecular Formula: C₁₃H₁₈O₆
• Molecular Weight: 270.282
• Mol file: 147852-45-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about cis-(1S,4R)-1-Acetoxy-4--2-cyclohexene 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: 99.0%

dimethyl malonate sodium salt (18424-76-5) + cis-1-acetoxy-4-chlorocyclohex-2-ene (82736-39-8) → cis-1-acetoxy-4-(dicarbomethoxymethyl)-2-cyclohexene (132541-04-9,82736-52-5,82736-53-6,147852-45-7,147852-46-8)

Guidance literature:

With palladium diacetate; triphenylphosphine; In tetrahydrofuran; for 0.75h; Ambient temperature;

DOI:10.1021/jo00233a023

Reference yield: 91.0%

sodiodimethylmalonate (18424-76-5) + cis-1-acetoxy-4-chlorocyclohex-2-ene (82736-39-8) → cis-1-acetoxy-4-(dicarbomethoxymethyl)-2-cyclohexene (132541-04-9,82736-52-5,82736-53-6,147852-45-7,147852-46-8)

Guidance literature:

With palladium diacetate; triphenylphosphine; In tetrahydrofuran; at 25 ℃; for 2h; Inert atmosphere;

DOI:10.15227/orgsyn.069.0038

Reference yield: 56.0%

cis-2-cyclohexenyl-1,4-diacetate (78776-45-1) + sodiodimethylmalonate (18424-76-5) → cis-(1S,4R)-1-Acetoxy-4--2-cyclohexene (147852-45-7) + cis-(1R,4S)-1-Acetoxy-4--2-cyclohexene (147852-46-8) + tetramethyl 2,2′-(cyclohex-2-ene-1,4-diyl)-dimalonate (109803-00-1)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); (+)-3-(diphenylphosphino)butanoic acid; In tetrahydrofuran; at 30 ℃; for 8h; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(00)00080-X

upstream raw materials:

dimethyl malonate sodium salt

cis-1-acetoxy-4-chlorocyclohex-2-ene

cyclohexa-1,3-diene

sodiodimethylmalonate

Downstream raw materials:

2-[(1S,4R)-4-(Toluene-4-sulfonylamino)-cyclohex-2-enyl]-malonic acid dimethyl ester

dimethyl (2,4-cyclohexadien-1-yl)malonate

2-(2,4-cyclohexadienyl)acetic acid methyl ester

2-((1S,4R)-4-Acetoxy-cyclohex-2-enyl)-2-methoxycarbonyl-4-oxo-hexanedioic acid dimethyl ester