39124-46-4

Basic information

• Product Name: 2-Propenamide, 3-phenyl-, (Z)-
• CAS NO: 39124-46-4
• Molecular Formula: C9H9NO
• Molecular Weight: 147.177
• Mol File: 39124-46-4.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: 2-Propenamide, 3-phenyl-, (Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, 3-phenyl-, (Z)-(39124-46-4)
• EPA Substance Registry System: 2-Propenamide, 3-phenyl-, (Z)-(39124-46-4)

Safety Data

• Hazardous Substances Data: 39124-46-4(Hazardous Substances Data)

Upstream product

• 24840-05-9 (Z)-cinnamonitrile 
• 621-79-4 cinnamamide 
• 7664-93-9 sulfuric acid 
• 100-52-7 benzaldehyde 
• 683-57-8 bromo-acetic acid amide 
• 591-50-4 iodobenzene 
• 79-06-1 2-propenamide 
• 102-92-1 Cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 59015-50-8 (Z)-3-phenylacryloyl chloride 
• 140-10-3 cis-cinnamic acid 
• 4610-69-9 (Z)-ethyl cinnamate 
• 433231-66-4 C₂₀H₁₂F₁₂NO₃P 
• 7223-30-5 3-phenyl-propynoic acid amide 

Downstream Products

• 140-10-3 (E)-3-phenylacrylic acid 
• 118653-04-6 cis-N-methoxycarbonyl-2-phenylethenylamine 
• 621-79-4 cinnamamide 

Relevant articles and documents

Energy-Transfer-Mediated Photocatalysis by a Bioinspired Organic Perylenephotosensitizer HiBRCP

Energy transfer plays a special role in photocatalysis by utilizing the potential energy of the excited state through indirect excitation, in which a photosensitizer determines the thermodynamic feasibility of the reaction. Bioinspired by the energy-transfer ability of natural product cercosporin, here we developed a green and highly efficient organic photosensitizer HiBRCP (hexaisobutyryl reduced cercosporin) through structural modification of cercosporin. After structural manipulation, its triplet energy was greatly improved, and then, it could markedly promote the efficient geometrical isomerization of alkenes from the E-isomer to the Z-isomer. Moreover, it was also effective for energy-transfer-mediated organometallic catalysis, which allowed realization of the cross-coupling of aryl bromides and carboxylic acids through efficient energy transfer from HiBRCP to nickel complexes. Thus, the study on the relationship between structural manipulation and their photophysical properties provided guidance for further modification of cercosporin, which could be applied to more meaningful and challenging energy-transfer reactions.

Contra-thermodynamic E → Z isomerization of cinnamamides via selective energy transfer catalysis

A bio-inspired, photocatalytic E → Z isomerization of cinnamides is reported using inexpensive (?)-riboflavin (vitamin B2) under irradiation at λ = 402 nm. This operationally simple transformation is compatible with a range of amide derivatives including –NR2, –NHSO2R and N(Boc)2 (up to 99:1 Z:E). Selective energy transfer from the excited state photocatalyst to the starting E-isomer ensures that directionality is achieved: The analogous process with the Z-isomer is inefficient due to developing allylic strain causing chromophore deconjugation. This is supported by X-ray analysis and Stern-Volmer photo-quenching studies. Preliminary validation of the method in manipulating the conformation of a simple model Leu-enkephalin penta-peptide is disclosed via the incorporation of a cinnamamide-based amino acid.

Water as a Hydrogenating Agent: Stereodivergent Pd-Catalyzed Semihydrogenation of Alkynes

Palladium-catalyzed transfer semihydrogenation of alkynes using H2O as the hydrogen source and Mn as the reducing reagent is developed, affording cis- and trans-alkenes selectively under mild conditions. In addition, this method provides an efficient way to access various cis-1,2-dideuterioalkenes and trans-1,2-dideuterioalkenes by using D2O instead of H2O.