Diethyl 5-methylidenecyclohex-3-ene-1,1-dicarboxylate

Base Information

• Chemical Name: Diethyl 5-methylidenecyclohex-3-ene-1,1-dicarboxylate
• CAS No.: 94922-12-0
• Molecular Formula: C13H18O4
• Molecular Weight: 238.284
• DSSTox Substance ID: DTXSID90556425
• Nikkaji Number: J2.316.833B
• Wikidata: Q82437969
• Mol file: 94922-12-0.mol

Synonyms:94922-12-0;Diethyl 5-methylidenecyclohex-3-ene-1,1-dicarboxylate;DTXSID90556425;5-methylene-cyclohex-3-ene-1,1-dicarboxylic acid diethyl ester;diethyl 5-methylene-3-cyclohexene-1,1-dicarboxylate

Chemical Property of Diethyl 5-methylidenecyclohex-3-ene-1,1-dicarboxylate

Chemical Property:

• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 238.12050905
• Heavy Atom Count: 17
• Complexity: 336

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1(CC=CC(=C)C1)C(=O)OCC

Technology Process of Diethyl 5-methylidenecyclohex-3-ene-1,1-dicarboxylate

There total 10 articles about Diethyl 5-methylidenecyclohex-3-ene-1,1-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: 96.0%

2-Allyl-2-(2-methylene-but-3-enyl)-malonic acid diethyl ester → diethyl 5-methylenecyclohex-3-ene-1,1-dicarboxylate (94922-12-0)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; Ambient temperature;

DOI:10.1021/jo970877p

Reference yield: 73.0%

4,4-bis(ethoxycarbonyl)-1-hepten-6-yne (101268-55-7) → diethyl 5-methylenecyclohex-3-ene-1,1-dicarboxylate (94922-12-0)

Guidance literature:

Wilkinson's catalyst; In acetonitrile; for 24h; Heating;

DOI:10.1016/S0040-4020(01)86200-1

Reference yield: 59.0%

diethyl 2-(2-bromo-2-propenyl)-2-(2-propenyl)propanedioate (118453-14-8) → diethyl 5-methylenecyclohex-3-ene-1,1-dicarboxylate (94922-12-0)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; phenylboronic acid; In tetrahydrofuran; water; at 60 ℃; for 3h;

DOI:10.1021/jo025665t

upstream raw materials:

4,4-bis(ethoxycarbonyl)-1-hepten-6-yne

diethyl 2-(2-bromo-2-propenyl)-2-(2-propenyl)propanedioate

methanol

carbon monoxide