1610944-15-4

Basic information

• Product Name: methyl N-(3-phenylpropiolyl)-L-phenylalaninate
• Synonyms: methyl N-(3-phenylpropiolyl)-L-phenylalaninate
• CAS NO: 1610944-15-4
• Molecular Weight: 307.349
• Mol File: 1610944-15-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: methyl N-(3-phenylpropiolyl)-L-phenylalaninate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl N-(3-phenylpropiolyl)-L-phenylalaninate(1610944-15-4)
• EPA Substance Registry System: methyl N-(3-phenylpropiolyl)-L-phenylalaninate(1610944-15-4)

Safety Data

• Hazardous Substances Data: 1610944-15-4(Hazardous Substances Data)

Upstream product

• 637-44-5 phenylpropyolic acid 
• 1027921-70-5 C₁₄H₁₄O₄ 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 536-74-3 phenylacetylene 
• 201230-82-2 carbon monoxide 
• 932-88-7 1-iodo-2-phenylethyne 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 7342-02-1 3-phenylpropynoic acid phenylamide 
• 15028-44-1 DL-phenylalanine methyl ester 

Downstream Products

• 1610944-20-1 methyl (E)-3-(dimethylphenylsilyl)-3-phenylacryloyl-L-phenylalaninate 

Relevant articles and documents

Practical access to fluorescent 2,3-naphthalimide derivatives: Via didehydro-Diels-Alder reaction

A practical and efficient approach for the synthesis of fluorescent 2,3-naphthalimide derivatives has been developed from readily available starting materials via an intramolecular didehydro-Diels-Alder reaction, which proceeded well under room temperature, exhibiting a wide substrate scope and good functional group tolerance. The practicability of this methodology has been verified by one-step synthesis of the environmentally sensitive fluorophore 6-DMN on a gram scale with a shorter time, fewer steps and less waste disposal, and without the utilization of toxic transition metals. The present experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.

Efficient synthesis of alkynyl amides via aminocarbonylation of iodoalkynes

Iodoethynylbenzene as iodoalkyne model compound was aminocarbonylated with tert-butylamine under carbon monoxide atmosphere in the presence of in situ palladium(0) catalysts. The formation of the unsaturated carboxamide (alkynyl amide) is always accompanied by that of the Glaser coupling product, diphenylbutadiyne. The yield of the amide-forming reaction was optimised by the systematic variation of the phosphine ligand, carbon monoxide pressure and temperature. The scope of the reaction was investigated by using various primary and secondary amines including amino acid methyl esters as N-nucleophiles. 17α-(Iodoethynyl)-testosterone was also functionalised by using this methodology providing the corresponding 17α-(carboxamidoethynyl)-testosterone derivatives in up to 96% yields. The reaction was extended to 1-(iodoethynyl)cyclohex-1-ene and 1-iodohex-1-yne. Ethyl iodopropiolate gave the enamine type product by the addition of amine to the alkyne functionality which was formed from the iodoalkyne via deiodination under standard aminocarbonylation conditions. The bromo analogue, bromoethynylbenzene has shown lower reactivity than the corresponding iodo derivative.