121817-36-5

Basic information

• Product Name: 2-Propenamide,3-phenyl-N-[(1Z)-2-phenylethenyl]-, (2E)-
• Synonyms: 2-Propenamide,3-phenyl-N-(2-phenylethenyl)-, (Z,E)-; Lansiumamide A
• CAS NO: 121817-36-5
• Molecular Formula: C17H15 N O
• Molecular Weight: 249.312
• Mol File: 121817-36-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2-Propenamide,3-phenyl-N-[(1Z)-2-phenylethenyl]-, (2E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide,3-phenyl-N-[(1Z)-2-phenylethenyl]-, (2E)-(121817-36-5)
• EPA Substance Registry System: 2-Propenamide,3-phenyl-N-[(1Z)-2-phenylethenyl]-, (2E)-(121817-36-5)

Safety Data

• Hazardous Substances Data: 121817-36-5(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 
• 932-88-7 1-iodo-2-phenylethyne 
• 621-79-4 cinnamamide 
• 57918-63-5 (Z)-styryl iodide 
• 98-80-6 phenylboronic acid 
• 30094-01-0 (E)-(2-phenylethenyl)magnesium bromide 
• 56920-25-3 cis-3-phenyl-2-trimethylsilyloxirane 
• 19319-11-0 (Z)-1-phenyl-2-(trimethylsilyl)ethylene 
• 4950-65-6 (2S)-3-phenyl-2-{[(E)-3-phenyl-2-propenoyl]amino}propanoic acid 
• 757967-40-1 (2E)-3-phenyl-N-[2-phenyl-1-(phenylthio)ethyl]acrylamide 
• 757967-42-3 (2E)-N-(1-hydroxy-2-phenylethyl)-3-phenylacrylamide 
• 122-78-1 phenylacetaldehyde 
• 757967-41-2 (2E)-3-phenyl-N-[2-phenyl-1-(phenylsulfonyl)ethyl]acrylamide 

Downstream Products

• 77527-97-0 (2E)-N-methyl-3-phenyl-N-[(E)-2-phenylvinyl]acrylamide 
• 121817-37-6 (2E)-N-methyl-3-phenyl-N-[(Z)-2-phenylvinyl]acrylamide 
• 3988-65-6 5-phenyl-2-[(E)-2-phenylethenyl]-1,3-oxazole 

Relevant articles and documents

Synthesis and fungicidal activity of lansiumamide A and B and their derivatives

A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B (N-methyl-N-cis-styryl-cinnamamide, 2) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS,1H NMR, and13C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide antifungal spectrum. The relationship between different substituents on the amide nitrogen and antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of N-substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the antifungal activities.

Concise and gram-scale total synthesis of lansiumamides A and B and alatamide

The total synthesis of potent anti-obesity lansiumamide B was accomplished in four steps using commercially available materials. The synthetic strategy, featured with copper-catalyzed Buchwald coupling, is concise, convergent, practical and can be carried out on a one-gram scale. This approach could give either Z- or E-configured enamide moiety in natural products with absolute stereocontrol and was applied in the total synthesis of natural products.

Synthesis of botryllamides and lansiumamides via ruthenium-catalyzed hydroamidation of alkynes

Ruthenium-catalyzed hydroamidations of alkynes allow a concise synthetic entry to both E- and Z-configured enamide natural products. This was demonstrated by the synthesis of botryllamides C and E, lansiumamides A and B, and lansamide I in 1-3 steps and 57-98% yield from simple, commercially available precursors. Georg Thieme Verlag Stuttgart New York.