51978-94-0

Basic information

• Product Name: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-, (E)-
• Synonyms: 3-methyl-4-nitro-5-styrylisoxazole;3-methyl-4-nitro-5-styryl-isoxazole;3-methyl-4-nitro-5-styryl isoxazole;3-methyl-5-styryl-4-nitroisoxazol;3-methyl-4-nitro-5-trans-styryl-isoxazole;3-Methyl-4-nitro-5-trans(?)-styryl-isoxazol
• CAS NO: 51978-94-0
• Molecular Formula: C12H10N2O3
• Molecular Weight: 230.223
• Mol File: 51978-94-0.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-, (E)-(51978-94-0)
• EPA Substance Registry System: Isoxazole, 3-methyl-4-nitro-5-(2-phenylethenyl)-, (E)-(51978-94-0)

Safety Data

• Hazardous Substances Data: 51978-94-0(Hazardous Substances Data)

Upstream product

• 123-54-6 acetylacetone 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 79510-57-9 3-<1-phenyl-2-(3-methyl-4-nitro-5-isoxazolyl)-ethyl>pentane-2,4-dione 
• 1123-49-5 3,5-dimethyl-4-nitroisoxazole 
• 100-52-7 benzaldehyde 

Downstream Products

• 51978-96-2 (E)-4-amino-3-methyl-5-styrylisoxazole 
• 103806-26-4 ethyl 2-<1-phenyl-2-(3-methyl-4-nitro-5-isoxazolyl)-ethyl>acetoacetate 
• 79510-57-9 3-<1-phenyl-2-(3-methyl-4-nitro-5-isoxazolyl)-ethyl>pentane-2,4-dione 
• 929719-07-3 3-(3-methyl-4-nitroizoxazol-5-yl)-2-phenylpropionic acid 
• 929719-10-8 3-(5-methyl-4-nitro-2H-pyrazol-3-yl)-2-phenylpropionic acid 
• 78636-44-9 5-[2-(3,5-dimethylisoxazol-5-yl)-2-phenylethyl]-3-methyl-4-nitroisoxazole 
• 140-10-3 (E)-3-phenylacrylic acid 
• 132869-20-6 ethyl 2-carbethoxy-4-(3-methyl-4-nitroisoxazol-5-yl)-3-phenylbutyrate 
• 65037-39-0 trans-1,3-di-(3-methyl-4-nitroisoxazol-5-yl)-trans-2,cis-4-diphenylcyclobutane 
• 70395-96-9 <1α(E),5α,6β,7α>-4-methyl-7-(3-methyl-4-nitro-5-isoxazolyl)-5-nitro-6-phenyl-1-styryl-2-oxa-3-azabicyclo<3.2.0>hept-3-ene 
• 70427-99-5 3,3'-dimethyl-4,4'-dinitro-5,5'-(2t,4t-diphenyl-cyclobutane-1r,3c-diyl)-bis-isoxazole 
• 70395-97-0 3,3'-dimethyl-4,4'-dinitro-5,5'-(3c,4t-diphenyl-cyclobutane-1r,2t-diyl)-bis-isoxazole 

Relevant articles and documents

Chiral 4 and 5 - disubstituted pyrrolidine -2 - ketone compound as well as preparation method and application thereof

The invention belongs to the technical field of organic synthesis, and particularly relates to chiral 4, 5 - disubstituted pyrrolidine -2 - ketone compounds as well as a preparation method and application thereof. The invention firstly uses nitro substituted alkyl (I) and trans α, β - unsaturated 3 - methyl -4 - nitroisoxazole (II) as raw materials, and the asymmetric Michael addition reaction of chiral superbase catalysis I and II is a key step and is hydrolyzed. Esterification and reduction closes the ring, synthesizing a chiral 3, 4 - disubstituted pyrrolidine -2 - ketone compound, including optically pure fenoxone. The asymmetric Michael addition reaction of chiral superbase catalyst for catalyzing 2 -substituted nitroethane (I) and trans α, β -unsaturated 3 - methyl -4 - nitroisoxazole (II) is used for preparing chiral 4 and 5 -disubstituted pyrroli -2 - ketone, and a strapdown is provided for synthesizing chiral 4 and 5 - disubstituted pyrrolidine -2 - ketone skeleton.

Structure–activity relationships of GPX4 inhibitor warheads

Direct inhibition of GPX4 requires covalent modification of the active-site selenocysteine. While phenotypic screening has revealed that activated alkyl chlorides and masked nitrile oxides can inhibit GPX4 covalently, a systematic assessment of potential electrophilic warheads with the capacity to inhibit cellular GPX4 has been lacking. Here, we survey more than 25 electrophilic warheads across several distinct GPX4-targeting scaffolds. We find that electrophiles with attenuated reactivity compared to chloroacetamides are unable to inhibit GPX4 despite the expected nucleophilicity of the selenocysteine residue. However, highly reactive propiolamides we uncover in this study can substitute for chloroacetamide and nitroisoxazole warheads in GPX4 inhibitors. Our observations suggest that electrophile masking strategies, including those we describe for propiolamide- and nitrile-oxide-based warheads, may be promising for the development of improved covalent GPX4 inhibitors.

Catalytic enantioselective addition of isocyanoacetate to 3-methyl-4-nitro-5-styrylisoxazoles under phase transfer catalysis conditions

The reaction between 3-methyl-4-nitro-5-styrylisoxazoles and ethyl isocyanoacetate proceeded under phase transfer catalysis to give enantioenriched monoadducts in high enantiomeric excess (up to 99% ee). The resulting adducts were subsequently cyclised to give 2,3-dihydropyrroles and substituted pyrrolidines in identical high ees and as a single diastereoisomer.