28917-17-1

Basic information

• Product Name: 3-phenyl-5-vinyl-1,2,4-oxadiazole
• Synonyms: 3-phenyl-5-vinyl-1,2,4-oxadiazole
• CAS NO: 28917-17-1
• Molecular Weight: 172.186
• Mol File: 28917-17-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3-phenyl-5-vinyl-1,2,4-oxadiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-phenyl-5-vinyl-1,2,4-oxadiazole(28917-17-1)
• EPA Substance Registry System: 3-phenyl-5-vinyl-1,2,4-oxadiazole(28917-17-1)

Safety Data

• Hazardous Substances Data: 28917-17-1(Hazardous Substances Data)

Upstream product

• 25740-75-4 N'-(acryloyloxy)benzenecarboximidamide 
• 100-47-0 benzonitrile 
• 613-92-3 N-hydroxybenzenecarboximidamide 
• 698-16-8 benzohydroximoyl chloride 
• 10480-43-0 N-allyl-N'-hydroxybenzimidamide 

Downstream Products

• 1236273-64-5 C₁₃H₁₆N₂O₂ 
• 1236273-66-7 C₁₄H₁₈N₂O 
• 770670-07-0 C₁₄H₁₉N₃O 
• 1236273-63-4 C₁₂H₁₄N₂O₂ 
• 1236273-61-2 C₁₄H₁₈N₂OS 
• 1236273-62-3 C₁₆H₁₄N₂OS 
• 748093-30-3 C₁₄H₁₉N₃O 
• 959-14-8 oxolamine 
• 1043431-25-9 C₁₄H₁₉N₃O 
• 1178714-74-3 C₁₆H₁₅N₃O 
• 1192934-08-9 C₁₇H₁₇N₃O 
• 1236273-65-6 C₁₇H₂₀N₂O₅ 

Relevant articles and documents

Development of Potent 3-Br-isoxazoline-Based Antimalarial and Antileishmanial Compounds

Starting from the structure of previously reported 3-Br-isoxazoline-based covalent inhibitors of P. falciparum glyceraldehyde 3-phosphate dehydrogenase, and with the intent to improve their metabolic stability and antimalarial activity, we designed and synthesized a series of simplified analogues that are characterized by the insertion of the oxadiazole ring as a bioisosteric replacement for the metabolically labile ester/amide function. We then further replaced the oxadiazole ring with a series of five-membered heterocycles and finally combined the most promising structural features. All the new derivatives were tested in vitro for antimalarial as well as antileishmanial activity. We identified two very promising new lead compounds, endowed with submicromolar antileishmanial activity and nanomolar antiplasmodial activity, respectively, and a very high selectivity index with respect to mammalian cells.

Synthesis of 1,2,4-Oxadiazoles via DDQ-Mediated Oxidative Cyclization of Amidoximes

An oxidative cyclization of amidoximes to form 1,2,4-oxadiazoles, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), is described. A range of alkyl, aryl, and heteroaryl substrates are tolerated under these conditions. This reaction serves as an alternate approach for the synthesis of functionally diverse oxadiazoles via a rapid and straightforward synthetic procedure.

Facile solid-phase organic synthesis of 5-vinyl-substituted 1,2,4-oxadiazoles from polymer-bound α-selenopropionic acid

Cyclocondensation of polystyrene-supported α-selenopropionic acid with amidoximes in the presence of l-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC) followed by oxidative deselenation efficiently afforded 5-vinyl 1,2,4-oxadiazoles in good yield and purity with a facile work-up procedure.