171815-69-3

Basic information

• Product Name: 1-(benzotriazol-1-yl)propargyl ethyl ether
• Synonyms: 1-(benzotriazol-1-yl)propargyl ethyl ether
• CAS NO: 171815-69-3
• Molecular Weight: 277.326
• Mol File: 171815-69-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 1-(benzotriazol-1-yl)propargyl ethyl ether(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(benzotriazol-1-yl)propargyl ethyl ether(171815-69-3)
• EPA Substance Registry System: 1-(benzotriazol-1-yl)propargyl ethyl ether(171815-69-3)

Safety Data

• Hazardous Substances Data: 171815-69-3(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 171815-58-0 (α-ethoxypropargyl)benzotriazole 
• 95-14-7 1,2,3-Benzotriazole 
• 6142-95-6 phenylpropargyl aldehyde diethyl acetal 
• 536-74-3 phenylacetylene 

Downstream Products

• 171815-71-7 3-(Benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-pentyne 
• 171815-74-0 3-(Benzotriazol-1-yl)-3-ethoxy-4-hydroxy-1,4,4-triphenyl-1-butyne 
• 301171-01-7 3-(Benzotriazol-1-yl)-3-ethoxy-4-hydroxy-4-(4-methylphenyl)-1-phenyl-1-butyne 
• 171815-72-8 3-(Benzotriazol-1-yl)-3-ethoxy-6-methyl-1-phenyl-1-heptyne 
• 171815-77-3 3-(Benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-nonadecyne 
• 171815-56-8 Ethyl 2-(benzotriazol-1-yl)-2-ethoxy-4-phenyl-3-butynoate 
• 171815-57-9 3-(Benzotriazol-1-yl)-3-ethoxy-1-phenyl-3-<(tert-butylamino)carbonyl>-1-butyne 
• 180967-60-6 6-(Benzotriazol-1-yl)-6-ethoxy-2,2-dimethyl-8-phenylocta-3,7-diyn-5-ol 
• 303047-00-9 1-(1-Ethoxy-1-phenylethynyl-nonyl)-1H-benzotriazole 
• 77267-31-3 1,10-diphenyl-1,9-decadiyne-3,8-dione 
• 21772-15-6 1-Phenyl-1-pentyne-3,4-dione 
• 171815-81-9 3-(Benzotriazol-1-yl)-3-ethoxy-4-hydroxy-4-methyl-1-phenyl-1-pentyne 
• 171815-55-7 3-(Benzotriazol-1-yl)-3-ethoxy-1-phenyl-1-pentyn-4-one 
• 171815-76-2 3-(Benzotriazol-1-yl)-3-ethoxy-1,4-diphenyl-1-butyne 

Relevant articles and documents

Lewis-acid-catalyzed asymmetric alkynylation of alkynyl 1,2-diketones: Controllable formation of 3(2 H)-furanones and α-hydroxy ketones

We report the highly regio- and enantioselective alkynylation of alkynyl 1,2-diketones under Lewis acid catalysis, leading to the formation of a series of biologically important 3(2H)-furanones with high to excellent ee values. Moreover, a slight change of the reaction conditions produces a range of highly functionalized α-hydroxy ketones with a high level of enantioselectivity. A variety of further transformations can be easily achieved, demonstrating the synthetic potential of this protocol.

N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones

The umpolung of alkynyl 1,2-diketones via N-heterocyclic carbene (NHC) catalysis was achieved for the first time, allowing the rapid access to a large variety of synthetically and pharmaceutically important α-pyrones under very mild conditions. A completely new NHC-catalyzed umpolung pattern involving an O-acylated allenolate as the key intermediate was proposed. Moreover, an unprecedented reaction pathway, featured by a series of group migrations and new bond formation, was postulated to demonstrate the formation of the products. (Figure presented.).

Novel and Convenient Routes to Functionalized Alkynyl Ketones from 1-(Benzotriazol-1-yl)propargyl Ethyl Ethers

1-(Benzotriazol-1-yl)propargyl ethyl ethers, readily accessible from propargyl aldehyde diethyl acetals and benzotriazole, undergo smooth lithiation at the methine carbon and subsequent reactions with alkyl halides, aldehydes, ketones, imines, esters, trialkylsilyl chlorides, dialkyl carbonates, and isocyanates to yield the corresponding substituted ethers.Hydrolysis of these intermediates under acidic conditions affords a wide variety of alkynyl ketones bearing hydroxy, amino, acyl, trimethylsilyl, alkoxycarbonyl, and (alkylamino)carbonyl substituents at the α-position in good to excellent overall yields.