Methyl 2-cyano-3-methoxy-3-phenylprop-2-enoate

Base Information

• Chemical Name: Methyl 2-cyano-3-methoxy-3-phenylprop-2-enoate
• CAS No.: 14533-94-9
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• DSSTox Substance ID: DTXSID30709650
• Mol file: 14533-94-9.mol

Synonyms:Methyl 2-cyano-3-methoxy-3-phenylprop-2-enoate;14533-94-9;SCHEMBL9228875;DTXSID30709650;methyl 3-methoxy-2-cyano-3-phenylpropenoate

Chemical Property of Methyl 2-cyano-3-methoxy-3-phenylprop-2-enoate

Chemical Property:

• XLogP3: 1.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 331

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=C(C#N)C(=O)OC)C1=CC=CC=C1

Technology Process of Methyl 2-cyano-3-methoxy-3-phenylprop-2-enoate

There total 2 articles about Methyl 2-cyano-3-methoxy-3-phenylprop-2-enoate 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: 52.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + Methyl 2-Cyano-3-oxo-3-phenylpropanoate (3239-71-2) → Z-Methyl 2-Cyano-3-methoxy-3-phenylpropenoate (14533-94-9) + Methyl (E)-2-cyano-3-methoxy-3-phenylpropenoate (14533-93-8)

Guidance literature:

In diethyl ether; at 0 ℃; for 1h; Title compound not separated from byproducts;

Reference yield:

benzoyl chloride (98-88-4) → Z-Methyl 2-Cyano-3-methoxy-3-phenylpropenoate (14533-94-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Na / 1) ether, methanol room temperature, 1 d; 2) reflux, 3 h;

2: diethyl ether / 1 h / 0 °C

With sodium; In diethyl ether;

Reference yield: 77.0%

Z-Methyl 2-Cyano-3-methoxy-3-phenylpropenoate (14533-94-9) + Methyl thioglycolate (2365-48-2) → Methyl-2-cyano-3-hydroxycinnamate (59551-61-0) + 4-Cyano-3-hydroxy-5-phenyl-thiophene-2-carboxylic acid methyl ester (85092-68-8)

Guidance literature:

With potassium acetate; In methanol; for 1h; Heating;

DOI:10.1055/s-1982-30063

upstream raw materials:

diazomethane

Methyl 2-Cyano-3-oxo-3-phenylpropanoate

benzoyl chloride

Downstream raw materials:

2-cyano-3-methylamino-3-phenyl-acrylic acid methyl ester

4-Oxo-2-phenyl-4H-9-thia-4a-aza-fluorene-1,3-dicarbonitrile

(1E,3Z)-methyl 4-cyano-1-methyl-1-methylthio-3-phenyl-2-azabuta-1,3-diene-4-carboxylate

Methyl-2-cyano-3-hydroxycinnamate