Diethyl 3-methylidenecyclopropane-1,2-dicarboxylate

Base Information

• Chemical Name: Diethyl 3-methylidenecyclopropane-1,2-dicarboxylate
• CAS No.: 7417-57-4
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• NSC Number: 175290
• DSSTox Substance ID: DTXSID10306308
• Nikkaji Number: J109.067D
• Mol file: 7417-57-4.mol

Synonyms:7417-57-4;1,2-Cyclopropanedicarboxylic acid, 3-methylene-, diethyl ester;diethyl 3-methylidenecyclopropane-1,2-dicarboxylate;NSC175290;SCHEMBL4857506;DTXSID10306308;VOHSAQPFAZSIES-UHFFFAOYSA-N;NSC-175290;Diethyl 3-methylene-1,2-cyclopropanedicarboxylate;Diethyl 3-methylenecyclopropane-1,2-dicarboxylate;Diethyl 3-methylene-1,2-cyclopropanedicarboxylate #

Chemical Property of Diethyl 3-methylidenecyclopropane-1,2-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.0122mmHg at 25°C
• Boiling Point: 260.5°Cat760mmHg
• Flash Point: 123.1°C
• Density: 1.11g/cm³
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 198.08920892
• Heavy Atom Count: 14
• Complexity: 243

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C(C1=C)C(=O)OCC

Technology Process of Diethyl 3-methylidenecyclopropane-1,2-dicarboxylate

There total 2 articles about Diethyl 3-methylidenecyclopropane-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:

ethyl 3-bromo-4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (18152-79-9) + ethanol (64-17-5) → 2,5-dimethylfuran-3-carboxylic acid (636-44-2) + diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate (7417-57-4,37608-33-6,55638-55-6,56221-92-2)

Guidance literature:

With potassium hydroxide; sulfuric acid; Yield given. Multistep reaction. Yields of byproduct given; reflux;

DOI:10.1021/jo01296a041

Reference yield:

ethyl 3-bromo-4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate (18152-79-9) → 2,5-dimethylfuran-3-carboxylic acid (636-44-2) + diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate (7417-57-4,37608-33-6,55638-55-6,56221-92-2)

Guidance literature:

Yield given. Multistep reaction. Yields of byproduct given;

DOI:10.1021/jo01296a041

Reference yield: 59.0%

N-(4-methoxybenzylidene)aniline oxide (3585-93-1) + diethyl 3-methylenecyclopropane-trans-1,2-dicarboxylate (7417-57-4,37608-33-6,55638-55-6,56221-92-2) → diethyl 7-(4-methoxyphenyl)-6-phenyl-5-oxa-6-azaspiro[2.4]heptan-1,2-dicarboxylate

Guidance literature:

In benzene; at 80 ℃; regioselective reaction;

DOI:10.1002/ejoc.200800975

upstream raw materials:

ethyl 3-bromo-4,6-dimethyl-2-oxo-2H-pyran-5-carboxylate

ethanol