95969-91-8

Basic information

• Product Name: 2-Propynamide, 3-phenyl-N-2-propenyl-
• CAS NO: 95969-91-8
• Molecular Formula: C12H11NO
• Molecular Weight: 185.225
• Mol File: 95969-91-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2-Propynamide, 3-phenyl-N-2-propenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propynamide, 3-phenyl-N-2-propenyl-(95969-91-8)
• EPA Substance Registry System: 2-Propynamide, 3-phenyl-N-2-propenyl-(95969-91-8)

Safety Data

• Hazardous Substances Data: 95969-91-8(Hazardous Substances Data)

Upstream product

• 107-11-9 1-amino-2-propene 
• 637-44-5 phenylpropyolic acid 
• 7342-02-1 3-phenylpropynoic acid phenylamide 
• 201230-82-2 carbon monoxide 
• 932-88-7 1-iodo-2-phenylethyne 
• 536-74-3 phenylacetylene 
• 4891-38-7 phenylpropynoic acid methyl ester 
• 84452-21-1 2-hydroxy-4-phenyl-3-butynenitrile 

Downstream Products

• 142671-85-0 6-Phenyl-2,3,3a,4-tetrahydro-cyclopenta[c]pyrrole-1,5-dione 
• 190449-96-8 CH₂CHCH₂NHCOC₂C₆H₅Co₂(CO)6 
• 1263037-03-1 (Z)-3-allyl-5-benzylideneoxazolidine-2,4-dione 
• 77302-27-3 (2E)-N-allyl-3-phenyl acrylamide 

Relevant articles and documents

N-triflyl-propiolamides: Preparation and transamidation reactions

N-Trifluoromethylsulfonyl-propiolamides have been prepared by two methods: a) N-triflation of secondary acetylenic carboxanilides, prepared in two steps from terminal alkynes, with triflic anhydride (Tf2O) and b) from terminal alkynes and an aryl or alkyl isocyanate followed by Tf2O in a consecutive one-pot reaction. The title compounds are bench-stable and insensitive to water and alcohols but amenable to transamidation reactions with a wide range of amine nucleophiles. Conversely, they are excellent reagents for the propynoylation of ammonia, primary and secondary amines, anilines, and hydrazines.

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.

Structural factors affecting the selectivities in the palladium(II) catalyzed cyclization of N-alkenyl-2-alkynamides

Palladium catalyzed cyclization of N-alkenyl 2-alkynamides occurred smoothly in the presence of CuCl2 and LiCl affording α-chloroalkylidene-γ-butyrolactams and α-chloroalkylidene-δ-valerolactams stereoselectively. The regioselectivity of the in