368453-52-5

Basic information

• Product Name: Benzonitrile, 4-(4-pentynyloxy)- (9CI)
• Synonyms: Benzonitrile, 4-(4-pentynyloxy)- (9CI)
• CAS NO: 368453-52-5
• Molecular Formula: C₁₂H₁₁NO
• Molecular Weight: 185.22184
• Product Categories: METHOXY
• Mol File: 368453-52-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzonitrile, 4-(4-pentynyloxy)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzonitrile, 4-(4-pentynyloxy)- (9CI)(368453-52-5)
• EPA Substance Registry System: Benzonitrile, 4-(4-pentynyloxy)- (9CI)(368453-52-5)

Safety Data

• Hazardous Substances Data: 368453-52-5(Hazardous Substances Data)

Upstream product

• 14267-92-6 1-chloro-4-pentyne 
• 767-00-0 4-cyanophenol 
• 106-41-2 4-bromo-phenol 
• 5390-04-5 pent-1-yn-5-ol 

Downstream Products

• 368453-53-6 5-methyl-3-[4-(pent-4-ynyloxy)phenyl]-1,2,4-oxadiazole 
• 368453-55-8 5-{3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}isoxazole-3-carboxylic acid 
• 368453-54-7 ethyl 5-{3-[4-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]propyl}isoxazole-3-carboxylate 

Relevant articles and documents

Hydroalkylation of Alkynes: Functionalization of the Alkenyl Copper Intermediate through Single Electron Transfer Chemistry

We have developed a method for the stereoselective coupling of terminal alkynes and α-bromo carbonyls to generate functionalized E-alkenes. The coupling is accomplished by merging the closed-shell hydrocupration of alkynes with the open-shell single electron transfer (SET) chemistry of the resulting alkenyl copper intermediate. We demonstrate that the reaction is compatible with various functional groups and can be performed in the presence of aryl bromides, alkyl chlorides, alkyl bromides, esters, nitriles, amides, and a wide range of nitrogen-containing heterocyclic compounds. Mechanistic studies provide evidence for SET oxidation of the alkenyl copper intermediate by an α-bromo ester as the key step that enables the cross coupling.

Novel pleconaril derivatives: Influence of substituents in the isoxazole and phenyl rings on the antiviral activity against enteroviruses

Today, there are no medicines to treat enterovirus and rhinovirus infections. In the present study, a series of novel pleconaril derivatives with substitutions in the isoxazole and phenyl rings was synthesized and evaluated for their antiviral activity against a panel of pleconaril-sensitive and -resistant enteroviruses. Studies of the structure-activity relationship demonstrate the crucial role of the N,N-dimethylcarbamoyl group in the isoxazole ring for antiviral activity against pleconaril-resistant viruses. In addition, one or two substituents in the phenyl ring directly impact on the spectrum of antienteroviral activity. The 3-(3-methyl-4-(3-(3-N,N-dimethylcarbamoyl-isoxazol-5-yl)propoxy)phenyl)-5-trifluoromethyl-1,2,4-oxadiazole 10g was among the compounds exhibiting the strongest activity against pleconaril-resistant as well as pleconaril-susceptible enteroviruses with IC50 values from 0.02 to 5.25 μM in this series. Compound 10g demonstrated markedly less CYP3A4 induction than pleconaril, was non-mutagenic, and was bioavailable after intragastric administration in mice. These results highlight compound 10g as a promising potential candidate as a broad spectrum enterovirus and rhinovirus inhibitor for further preclinical investigations.

αGal-conjugated anti-rhinovirus agents: Chemo-enzymatic syntheses and testing of anti-Gal binding

The syntheses of αGal-conjugated anti-rhinovirus agents 1, 2 and 3 and their abilities to inhibit αGal binding of human anti-Gal antibody are described. An efficient enzymatic glycosylation using a novel fusion protein serves to provide the key αGal inter