Propanedioic acid, (3,4-dimethoxyphenyl)-, diethyl ester

Base Information

• Chemical Name: Propanedioic acid, (3,4-dimethoxyphenyl)-, diethyl ester
• CAS No.: 896-90-2
• Molecular Formula: C15H20O6
• Molecular Weight: 296.32
• DSSTox Substance ID: DTXSID80399222
• Mol file: 896-90-2.mol

Synonyms:Propanedioic acid, (3,4-dimethoxyphenyl)-, diethyl ester;896-90-2;DTXSID80399222;AKOS011682484

Chemical Property of Propanedioic acid, (3,4-dimethoxyphenyl)-, diethyl ester

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 296.12598835
• Heavy Atom Count: 21
• Complexity: 325

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Propanedioic acid, (3,4-dimethoxyphenyl)-, diethyl ester

There total 5 articles about Propanedioic acid, (3,4-dimethoxyphenyl)-, diethyl ester 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: 97.0%

ethyl 3,4-dimethoxyphenylacetate (18066-68-7) + ethyl cyanoformate (623-49-4) → 2-(3,4-dimethoxyphenyl)malonic acid diethyl ester (896-90-2)

Guidance literature:

ethyl 3,4-dimethoxyphenylacetate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

ethyl cyanoformate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo8025912

Reference yield: 86.0%

ethyl 3,4-dimethoxyphenylacetate (18066-68-7) + Diethyl carbonate (105-58-8,76619-83-5) → 2-(3,4-dimethoxyphenyl)malonic acid diethyl ester (896-90-2)

Guidance literature:

With sodium ethanolate; In toluene; Heating;

Reference yield: 35.0%

ethyl 3,4-dimethoxyphenylacetate (18066-68-7) + oxalic acid diethyl ester (95-92-1) → 2-(3,4-dimethoxyphenyl)malonic acid diethyl ester (896-90-2)

Guidance literature:

With sodium ethanolate; In ethanol; 1) 20 deg C, 15 h, 2) 1 h, reflux;

upstream raw materials:

ethyl 3,4-dimethoxyphenylacetate

Diethyl carbonate

oxalic acid diethyl ester

ethyl cyanoformate

Downstream raw materials:

N,N'-Dicyclohexyl-2-(3,4-dimethoxy-phenyl)-malonamide

N,N-Diethyl-2-(3,4-dimethoxy-phenyl)malonamide

2-(3,4-dimethoxy-phenyl)-1,3-propane-diol

5-(3,4-dimethoxyphenyl)pyrimidine-4,6-diol

Refernces

• 1、 Matulenko, Mark A.,Paight, Ernest S.,Frey, Robin R.,Gomtsyan, Arthur,DiDomenico Jr., Stanley,Jiang, Meiqun,Lee, Chih-Hung,Stewart, Andrew O.,Yu, Haixia,Kohlhaas, Kathy L.,Alexander, Karen M.,McGaraughty, Steve,Mikusa, Joseph,Marsh, Kennan C.,Muchmore, Steven W.,Jakob, Clarissa L.,Kowaluk, Elizabeth A.,Jarvis, Michael F.,Bhagwat, Shripad S.. "4-Amino-5-aryl-6-arylethynylpyrimidines: Structure-activity relationships of non-nucleoside adenosine kinase inhibitors". . p. 1586 - 1605. Retrieved 2008/02/01.