3-BENZYLCARBAMOYL-ACRYLIC ACID

Base Information

• Chemical Name: 3-BENZYLCARBAMOYL-ACRYLIC ACID
• CAS No.: 685543-77-5
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Mol file: 685543-77-5.mol

Synonyms:trans-3-benzylcarbamoylacrylic acid;N-benzyl-fumaramic acid;trans-3-benzylcarbamoylpropenoic acid;fumaric acid monobenzylamide;N-Benzyl-fumaramidsaeure;fumaric acid monobenzyl amide;

Chemical Property of 3-BENZYLCARBAMOYL-ACRYLIC ACID

Chemical Property:

• PSA: 66.40000
• LogP: 1.33450

Purity/Quality:

99% ^*data from raw suppliers

(2E)-4-(Benzylamino)-4-oxobut-2-enoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-BENZYLCARBAMOYL-ACRYLIC ACID

There total 8 articles about 3-BENZYLCARBAMOYL-ACRYLIC ACID 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: 81.0%

4-oxo-4-[(phenylmethyl)amino]-(E)-2-butenoic acid ethyl ester (474024-61-8) → trans-3-(benzylcarbamoyl)acrylic acid (685543-77-5)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1021/jm701311r

Reference yield: 70.0%

(E)-4-ethoxy-4-oxobut-2-enoic acid (2459-05-4) + benzylamine (100-46-9) → trans-3-(benzylcarbamoyl)acrylic acid (685543-77-5)

Guidance literature:

(E)-4-ethoxy-4-oxobut-2-enoic acid; With oxalyl dichloride; N,N-dimethyl-formamide; In benzene; at 20 ℃; for 4h; Inert atmosphere;

benzylamine; With caesium carbonate; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

With potassium hydroxide; water; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1002/ejoc.200800781

Reference yield:

fumaric acid ethyl ester mono chloride (26367-48-6) + benzylamine (100-46-9) → trans-3-(benzylcarbamoyl)acrylic acid (685543-77-5)

Guidance literature:

fumaric acid ethyl ester mono chloride; benzylamine; With caesium carbonate; In tetrahydrofuran; at 20 ℃; for 12h;

With potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/j.tetlet.2004.11.115

upstream raw materials:

maleic anhydride

benzylamine

fumaryl dichloride

(2E)-but-2-enedioic acid

Downstream raw materials:

N₂-tert-butoxycarbonyl-N₁-carbamoylmethyl-N₁-trans-(3-benzylcarbonylpropenoyl)hydrazine

Refernces

• 1、 Ikoma, Minoru,Oikawa, Masato,Sasaki, Makoto. "Chemospecific allylation and domino metathesis of 7-oxanorbornenes for skeletal and appendage diversity". experimental part. p. 72 - 84. Retrieved 2009/06/18.
• 2、 Ekici, ?zlem Do?an,Li, Zhao Zhao,Campbell, Amy J.,James, Karen Ellis,Asgian, Juliana L.,Mikolajczyk, Jowita,Salvesen, Guy S.,Ganesan, Rajkumar,Jelakovic, Stjepan,Grütter, Markus G.,Powers, James C.. "Design, synthesis, and evaluation of aza-peptide Michael acceptors as selective and potent inhibitors of caspases-2, -3, -6, -7, -8, -9, and -10". . p. 5728 - 5749. Retrieved 2008/04/18.