1228932-02-2

Basic information

• Product Name: (E)-methyl 2-(azidomethyl)-5-phenylpent-2-en-4-ynoate
• Synonyms: (E)-methyl 2-(azidomethyl)-5-phenylpent-2-en-4-ynoate
• CAS NO: 1228932-02-2
• Molecular Weight: 241.249
• Mol File: 1228932-02-2.mol

Chemical Properties

• CAS DataBase Reference: (E)-methyl 2-(azidomethyl)-5-phenylpent-2-en-4-ynoate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-methyl 2-(azidomethyl)-5-phenylpent-2-en-4-ynoate(1228932-02-2)
• EPA Substance Registry System: (E)-methyl 2-(azidomethyl)-5-phenylpent-2-en-4-ynoate(1228932-02-2)

Safety Data

• Hazardous Substances Data: 1228932-02-2(Hazardous Substances Data)

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 1228931-75-6 methyl 3-hydroxy-2-methylene-5-phenylpent-4-ynoate 

Downstream Products

• 1228932-17-9 methyl 3-phenyl-6H-pyrrolo[1,2-c][1,2,3]triazole-5-carboxylate 
• 79600-43-4 methyl 5-benzoyl-1H-pyrrole-3-carboxylate 
• 4634-13-3 methyl 6-phenylnicotinate 

Relevant articles and documents

Copper-Catalyzed Intramolecular Chalcogenoamination of Enynyl Azides: Synthesis of 5-Selenyl/Sulfenyl Nicotinates

A novel methodology for the synthesis of 5-selenyl/sulfenyl nicotinates involving copper-catalyzed organochalcogenyl aza-annulation of enynyl azide with diorganyl-dichalcogenides has been described. This method offers difunctionalization of alkynes via regioselective intramolecular chalcogenoamination in one pot to provide substituted 5-chalcogenyl nicotinates in good to excellent yields. The resulting nicotinates provide access to their oxides, sulfones, and acid derivatives.

Cu(I)-Catalyzed Aminative Aza-Annulation of Enynyl Azide using N-Fluorobenzenesulfonimide: Synthesis of 5-Aminonicotinates

An unprecedented copper-catalyzed aminative aza-annulation of enynyl azide using commercially available N-fluorobenzenesulfonimide (NFSI) as an amination reagent is described. The reaction proceeds via regioselective inter-/intramolecular diamination, incorporating one nitrogen from the NFSI and the other from the azide, to provide amino-substituted nicotinate derivatives in a single step with moderate to high yield. This method represents an efficient way to access diverse aminonicotinates through direct C-N bond-coupling processes.

Aza-annulation of enynyl azides: A new approach to substituted pyridines

Synthesis of substituted pyridines through a novel aza-annulation of 2-en-4-ynyl azides, derived from MBH-acetates of acetylenic aldehydes, is described. A variety of enynyl azides having aryl, heteroaryl, and alkyl groups on the alkyne functionality successfully participated in the Ag-mediated annulation reaction to provide the corresponding 3,6-disubstituted pyridines. I2-Mediated cyclization was found to be controlled by the substituent on the alkyne functionality, which offered the 5-iodo-3,6-disubstituted pyridines from enynyl azides having an electron-rich substituent on the alkyne functionality.

3,5-Disubstituted 6H-pyrrolo[1,2-c][1,2,3]triazoles from Morita-Baylis-Hillman adducts of propargyl aldehydes

A simple method for synthesizing several 6H-pyrrolo[1,2-c][1,2,3]triazole derivatives having a methoxycarbonyl or an acetyl group at C-5 position and 7,8-dihydro-4H-[1,2,3]triazolo[1,5-a]indol-5(6H)-ones via an intramolecular 1,3-dipolar cycloaddition reaction of azido enynes, which were readily obtained from the Morita-Baylis-Hillman acetates of propargyl aldehydes with sodium azide, has been developed.