2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-

Base Information

• Chemical Name: 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-
• CAS No.: 65638-74-6
• Molecular Formula: C11H11NO3
• Molecular Weight: 205.213
• Mol file: 65638-74-6.mol

Synonyms:Z-Methyl-α-formamidocinnamat;(Z)-N-Formyldehydrophenylalanin-methylester;(Z)-methyl 2-formylamino-3-phenylacrylate;

Chemical Property of 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-

Chemical Property:

• PSA: 55.40000
• LogP: 1.97330

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)-

There total 5 articles about 2-Propenoic acid, 2-(formylamino)-3-phenyl-, methyl ester, (Z)- 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: 37.0%

isocyanoacetic acid methyl ester (39687-95-1) + benzaldehyde (100-52-7) → (E)-2-(formamido)cinnamic acid methyl ester (72053-02-2) + (Z)-N-Formyldehydrophenylalanin-methylester (65638-74-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; 1) 30 to 35 deg C, 2) RT, 2 h;

DOI:10.1248/cpb.28.2374

Reference yield:

benzaldehyde (100-52-7) → (Z)-N-Formyldehydrophenylalanin-methylester (65638-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: Cu₂O / diethyl ether / 3 h / 20 °C

2: t-BuOK / tetrahydrofuran; diethyl ether / 0.5 h / 0 °C

With copper(I) oxide; potassium tert-butylate; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo052451d

Reference yield:

bromobenzene (108-86-1,52753-63-6) + 2-(formamido)acrylic acid methyl ester (44804-84-4) → (E)-2-(formamido)cinnamic acid methyl ester (72053-02-2) + (Z)-N-Formyldehydrophenylalanin-methylester (65638-74-6)

Guidance literature:

With palladium diacetate; tetrabutyl-ammonium chloride; sodium hydrogencarbonate; at 80 ℃; for 22h;

DOI:10.1021/jo052451d

upstream raw materials:

isocyanoacetic acid methyl ester

benzaldehyde

bromobenzene

2-(formamido)acrylic acid methyl ester

Downstream raw materials:

N-formyl-phenylalanine

2-benzyl-2-formamidoacetic acid methyl ester

methyl (Z)-β-(1-imidazolyl)-α-isocyanocinnamate

methyl (E)-β-(1-imidazolyl)-α-isocyanocinnamate

Refernces

• 1、 Yamada, Masaki,Nakao, Kazuya,Fukui, Toshio,Nunami, Ken-Ichi. "(Z)-selective β-bromination of N-formyl-α,β-dehydroamino acid esters". . p. 5751 - 5764. Retrieved 2007/10/03.
• 2、 Suzuki,Nunami,Matsumoto,et al.. "Synthesis of antimicrobial activities of α-isocyanoacrylic acid derivatives". . p. 2374 - 2383. Retrieved 2007/10/02.