19202-21-2

Basic information

• Product Name: (E)-3-PHENYL-1-(PYRROLIDIN-1-YL)PROP-2-EN-1-ONE
• Synonyms: (E)-3-PHENYL-1-(PYRROLIDIN-1-YL)PROP-2-EN-1-ONE;1-(1-Oxo-3-phenyl-2-propenyl)pyrrolidine;1-(3-Phenylacryloyl)pyrrolidine;Pyrrolizinostyryl ketone
• CAS NO: 19202-21-2
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.26
• Mol File: 19202-21-2.mol
• Article Data: 38

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-3-PHENYL-1-(PYRROLIDIN-1-YL)PROP-2-EN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-PHENYL-1-(PYRROLIDIN-1-YL)PROP-2-EN-1-ONE(19202-21-2)
• EPA Substance Registry System: (E)-3-PHENYL-1-(PYRROLIDIN-1-YL)PROP-2-EN-1-ONE(19202-21-2)

Safety Data

• Hazardous Substances Data: 19202-21-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 91, p. 1233, 1969 DOI: 10.1021/ja01033a044The Journal of Organic Chemistry, 39, p. 3327, 1974 DOI: 10.1021/jo00937a004

Upstream product

• 15097-49-1 N-trimethylsilylpyrrolidine 
• 38986-89-9 trans-cinnamoyl fluoride 
• 100-52-7 benzaldehyde 
• 849693-82-9 1-[(diphenylphosphono)acetyl]pyrrolidine 
• 123-75-1 pyrrolidine 
• 140-10-3 (E)-3-phenylacrylic acid 
• 102-92-1 cinnamoyl chloride 
• 4030-18-6 N-(acetyl)pyrrolidine 
• 100-51-6 benzyl alcohol 
• 2033-24-1 cycl-isopropylidene malonate 
• 102-92-1 Cinnamoyl chloride 
• 42599-24-6 E-styryl iodide 
• 116858-81-2 trimethylpyrrolidinylcarbonylstannane 
• 104-55-2 3-phenyl-propenal 

Downstream Products

• 119163-37-0 ((2S,3R)-3-Phenyl-oxiranyl)-pyrrolidin-1-yl-methanone 
• 415917-73-6 [(1S,2S,3R)-2-Phenyl-3-((E)-2-trimethylsilanyl-vinyl)-cyclopropyl]-pyrrolidin-1-yl-methanone 
• 198982-11-5 [Ru2(μ-H)(μ-η(3)-PhC=CHC(O)N(CH2)4)(CO)6] 
• 425620-12-8 pentacarbonyl-(4-ethoxy-5-phenyl-2-pyrrolidinium-3-cyclopentenyl)tungstate 
• 1110635-81-8 C₂₇H₂₅NO 
• 1314705-35-5 C₁₄H₁₄O₆ 
• 1314705-58-2 dimethyl 2-[2-hydroxy-2-phenyl-1-(pyrrolidin-1-ylcarbonyl)ethyl]propanedioate 
• 1314705-52-6 dimethyl 2-hydroxy-2-[3-oxo-1-phenyl-3-(pyrrolidin-1-yl)propyl]propanedioate 
• 1314705-36-6 dimethyl dihydro-4-[2-methoxy-1-(methoxycarbonyl)-2-oxoethyl]-5-oxo-3-phenylfuran-2,2(3H)-dicarboxylate 
• 1314705-70-8 tetramethyl 2-phenyl-3-(pyrrolidin-1-ylcarbonyl)buta-1,3-diene-1,1,4,4-tetracarboxylate 

Relevant articles and documents

1,2-Asymmetric induction in the addition of XCCl3 to trans-cinnamoyl-N-pyrrolidine

In the reaction of XCCl3 (X = Br (1), Cl (2)) with trans-PhCH=CHC(O)Y (Y = N-pyrrolidinyl) (3) in the presence of Fe(CO)5 as the catalyst (or benzoyl peroxide in the case of 1) at 80 deg C, the addition of CCl3 radicals occurs regioselectively at the α-ca

Photocatalytic aldehydes/alcohols/toluenes oxidative amidation over bifunctional Pd/MOFs: Effect of Fe-O clusters and Lewis acid sites

Heterogeneous photocatalytic organic synthesis is fascinating because of the utilization of ubiquitous solar light for chemical transformations. Here, three Fe-MOFs with different Fe-O clusters, Lewis acid sites and morphologies were synthesized through coordination structure engineering. Pd/Fe-MOFs nanocomposites were used to challenge the amide bond green synthesis with visible light. Pd/MIL-101(Fe) exhibited the best photocatalytic performance due to the easily excited Fe3-μ3-oxo clusters for light absorption, the efficient photogenerated carriers separation and migration, the large amount of Lewis acid sites based aldehydes and amines condensation promotion and the efficient O2 reduction to superoxide radicals over photogenerated electron-rich Pd NPs. Various aldehydes, alcohols and toluenes could be transformed to amide compounds with amines over Pd/MIL-101(Fe) with just oxygen or air as the green oxidant and water as the by-product. One-pot C–C cross-coupling and photo-redox C–N coupling cascade reactions could also be achieved over Pd/MIL-101(Fe). This work shed light on the efficient and sustainable amide bonds synthesis.

Erratum: Photoenzymatic Reductions Enabled by Direct Excitation of Flavin-Dependent 'Ene'-Reductases (J. Am. Chem. Soc. (2021) 143:4 (1735-1739) DOI: 10.1021/jacs.0c11494)

Support by the Department of Energy was inadvertently left out of the Acknowledgments and a coauthor's name was misspelled in the Supporting Information. The scientific part of the manuscript remains unchanged. The complete correct Acknowledgment paragraph is as follows.

Rapid access to cinnamamides and piper amides: Via three component coupling of arylaldehydes, amines, and Meldrum's acid

A practical method for the synthesis of cinnamamides and piper amides via a conceptually novel three component reaction of aldehydes, amines and Meldrum's acid has been reported. The reaction proceeds under operationally simple conditions without the aid of coupling reagents, oxidants, or catalysts, which are essential for the preparation of cinnamamides/piper amides via known methods. The formation of undesired chemical wastes that generally originate from the use of coupling reagents, oxidants, or catalysts has been avoided to make this reaction more atom economical.