cis-Cinnamamide

Base Information

• Chemical Name: cis-Cinnamamide
• CAS No.: 39124-46-4
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• UNII: PEO59P6VC7
• Nikkaji Number: J370.612E
• Wikidata: Q27145881
• Mol file: 39124-46-4.mol

Synonyms:cis-cinnamamide;39124-46-4;Cinnamamide, (Z)-;(Z)-3-phenylprop-2-enamide;PEO59P6VC7;2-Benzylideneacetamide, (Z)-;2-Propenamide, 3-phenyl-, (2Z)-;UNII-PEO59P6VC7;(2Z)-3-phenylprop-2-enamide;cis-beta-(Aminocarbonyl)styrene;2-Propenamide, 3-phenyl-, (Z)-;(Z)-Cinnamamide;SCHEMBL3239009;CHEBI:76321;CIS-.BETA.-(AMINOCARBONYL)STYRENE;EN300-6477850;Q27145881

Chemical Property of cis-Cinnamamide

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 147.068413911
• Heavy Atom Count: 11
• Complexity: 157

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C=CC(=O)N
• Isomeric SMILES: C1=CC=C(C=C1)/C=C\C(=O)N

Technology Process of cis-Cinnamamide

There total 18 articles about cis-Cinnamamide 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: 98.0%

cinnamamide (621-79-4,22031-64-7) → (Z)-3-phenylacrylamide (39124-46-4)

Guidance literature:

With riboflavin; In acetonitrile; at 20 ℃; for 24h; UV-irradiation;

DOI:10.1016/j.tet.2020.131198

Reference yield: 83.0%

3-phenyl-propynoic acid amide (7223-30-5) → (Z)-3-phenylacrylamide (39124-46-4)

Guidance literature:

With manganese; water; palladium diacetate; In acetonitrile; at 25 ℃; for 24h; diastereoselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.orglett.9b00148

Reference yield:

(Z)-cinnamonitrile (24840-05-9) + sulfuric acid (7664-93-9) → (E)-3-phenylacrylic acid (140-10-3) + (Z)-3-phenylacrylamide (39124-46-4)

Guidance literature:

anschliessend Behandeln mit wss. Natriumcarbonat-Loesung;

upstream raw materials:

3-phenyl-propynoic acid amide

(Z)-cinnamonitrile

cinnamamide

sulfuric acid

Downstream raw materials:

(E)-3-phenylacrylic acid

cinnamamide

cis-N-methoxycarbonyl-2-phenylethenylamine

Refernces

• 1、 Zhang, Yan,Xia, Mingze,Li, Min,Ping, Qian,Yuan, Zhenbo,Liu, Xuanzhong,Yin, Huimin,Huang, Shuping,Rao, Yijian. "Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP". . p. 15284 - 15297. Retrieved 2021/11/01.
• 2、 Xu, Jianbin,Liu, Na,Lv, Haiping,He, Chixian,Liu, Zining,Shen, Xianfu,Cheng, Feixiang,Fan, Baomin. "Photocatalyst-free visible light promoted: E → Z isomerization of alkenes". supporting information. p. 2739 - 2743. Retrieved 2020/06/17.