Dimethyl 4-oxocyclohex-2-ene-1,2-dicarboxylate

Base Information

• Chemical Name: Dimethyl 4-oxocyclohex-2-ene-1,2-dicarboxylate
• CAS No.: 81787-83-9
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.202
• DSSTox Substance ID: DTXSID80512898
• Mol file: 81787-83-9.mol

Synonyms:Dimethyl 4-oxocyclohex-2-ene-1,2-dicarboxylate;81787-83-9;DTXSID80512898

Chemical Property of Dimethyl 4-oxocyclohex-2-ene-1,2-dicarboxylate

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 212.06847348
• Heavy Atom Count: 15
• Complexity: 329

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(=O)C=C1C(=O)OC

Technology Process of Dimethyl 4-oxocyclohex-2-ene-1,2-dicarboxylate

There total 2 articles about Dimethyl 4-oxocyclohex-2-ene-1,2-dicarboxylate 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:

4-Trimethylsilanyloxy-cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester → 4-Oxo-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester (81787-83-9)

Guidance literature:

In methanol; for 48h;

DOI:10.1139/v82-063

Reference yield:

dimethyl acetylenedicarboxylate (762-42-5) → 4-Oxo-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester (81787-83-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / benzene / 24 h / 65 °C

2: 12.5 g / methanol / 48 h

In methanol; benzene;

DOI:10.1139/v82-063

Reference yield:

4-Oxo-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester (81787-83-9) → (1S,4R)-4-Hydroxy-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester + (1S,4S)-4-Hydroxy-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester + (1R,4R)-4-Hydroxy-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester + (1R,4S)-4-Hydroxy-cyclohex-2-ene-1,2-dicarboxylic acid dimethyl ester

Guidance literature:

With formic acid; triethylamine; (R,R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In 1,2-dichloro-ethane; at 22 ℃; for 15h; Title compound not separated from byproducts;

DOI:10.1016/j.tetasy.2006.10.012

upstream raw materials:

dimethyl acetylenedicarboxylate