1008-74-8

Usage

Uses

Used in Pharmaceutical Industry:
Isoxazole, 5-methyl-3-phenyl(7CI,8CI,9CI), is used as a building block for the synthesis of various pharmaceutical compounds due to its potential biological activity. Its unique structure allows it to be incorporated into drug molecules, potentially enhancing their therapeutic effects and targeting specific biological pathways.
Used in Agrochemical Industry:
Isoxazole, 5-methyl-3-phenyl(7CI,8CI,9CI), is utilized in the agrochemical industry for the development of new pesticides and other agrochemical products. Its chemical properties and potential biological activity make it a valuable component in the creation of effective and targeted agrochemicals.
Used in Other Industrial Applications:
Due to its structural and chemical properties, Isoxazole, 5-methyl-3-phenyl(7CI,8CI,9CI), may also have applications in other industries, such as materials science, where it could be used to develop new materials with specific properties or functions. Its versatility and potential for further chemical modification make it a promising candidate for various industrial applications.

InChI:InChI=1/C10H9NO/c1-8-7-10(11-12-8)9-5-3-2-4-6-9/h2-7H,1H3

Upstream product

• 495-41-0 1-phenylbut-2-en-1-one 
• 1817-57-8 4-phenyl-3-butyne-2-one 
• 2039-50-1 5-bromomethyl-3-phenyl-isoxazole 
• 5221-67-0 5-methyl-2-phenyloxazole 
• 51315-04-9 1-(3-phenyl-2H-azirin-2-yl)-ethanone 
• 1136-45-4 5-methyl-3-phenylisoxazol-4-carboxylic acid 
• 93-91-4 1-phenylbutan-1,3-dione 
• 53120-17-5 1-phenyl-1,3-pentanedionedioxime 
• 147137-26-6 1-Phenyl-but-3-yn-1-one oxime 
• 4749-28-4 2-nitropropene 
• 698-16-8 benzohydroximoyl chloride 
• 873-67-6 benzonitrile oxide 
• 463-49-0 1,2-propanediene 
• 7803-49-8 hydroxylamine 

Downstream Products

• 62679-05-4 5-methylsulfanylmethyl-3-phenyl-isoxazole 
• 3919-84-4 2-(3-phenylisoxazol-5-yl)acetic acid 
• 57354-90-2 5-methyl-3-phenyl-4-nitroisoxazole 
• 80949-40-2 4,4-Dichloro-5-methoxy-5-methyl-3-phenyl-4,5-dihydro-isoxazole 
• 139193-82-1 5-[(E)-2-(2-Methoxy-phenyl)-vinyl]-3-phenyl-isoxazole 
• 1441-42-5 3-phenyl-5-styrylisoxazole 
• 156088-10-7 3-phenyl-5-(tert-butyldimethylsilyl)methylisoxazole 
• 139193-97-8 Dimethyl-{4-[(E)-2-(3-phenyl-isoxazol-5-yl)-vinyl]-phenyl}-amine 
• 69209-40-1 methyl 2-methyl-6-phenylpyridine-4-carboxylate 
• 6237-59-8 hexamethyl benzenehexacarboxylate 
• 87444-85-7 3,4-bis(methoxycarbonyl)-2-methyl-6-phenylpyridine 
• 79344-02-8 3-phenyl-4,4-dichloro-5-methyl-5-hydroxy-Δ²-isoxaline 
• 31295-65-5 4-bromo-5-methyl-3-phenylisoxazole 
• 139193-84-3 2-[(E)-2-(3-Phenyl-isoxazol-5-yl)-vinyl]-phenol 

Relevant academic research and scientific papers

Structural Investigation of 3,5-Disubstituted Isoxazoles by 1H-Nuclear Magnetic Resonance

HIV-1 integrase (IN) is a very promising and validated target for the development of therapeutic agents against AIDS. In an effort to design and synthesize biological isosteric analogs of β-diketoacid-containing inhibitors of IN, we prepared a series of s

Heteropolyacids as green and reusable catalysts for the synthesis of isoxazole derivatives

Heteropolyanions with different structures, including Keggin, Dawson, Preyssler, mixed addenda, and sandwich types, catalyzed the formation of 1,3-diphenyl-isoxazole from the condensation of 1,3-diphenyl-propane-1,3-dione and hydroxylamine hydrochloride in different solvents and under heating conditions. Our data vividly indicate that H3PW11CuO40 is the catalyst of choice and could catalyze the synthesis of other isoxazole derivatives in high yields and good selectivities. Copyright Taylor & Francis Group, LLC.

Dehydrochlorination of Hydroximoyl Chlorides by the Use of Vinyltins for Synthesis of Isoxazolines (Dihydrooxazoles)

The reaction of hydroximoyl chlorides and vinyltin compounds afforded isoxazolines via dehydrochlorination and dipolar cycloaddition.

Continuous-flow microliter microwave irradiation in the synthesis of isoxazole derivatives: An optimization procedure

An efficient method was developed for the synthesis of 3,4,5-trisubstituted and 3,5-disubstituted isoxazoles by using continuous-flow microwave-heated microreactors. A study on the separate effects of the temperature, continuous-flow regime, and microwave irradiation showed that the continuous-flow regime had important effects for less reactive diketones, where microwave heating enhanced the reaction, permitting the formation of 5-methyl-3-phenylisoxazole, which was not formed in the absence of microwaves. Georg Thieme Verlag Stuttgart · New York.

Hexacarbonylmolybdenum-induced Reaction of Isoxazoles. Cycloaddition of Isoxazoles with Acetylenic Esters and Related Reactions

In the presence of hexacarbonylmolybdenum, substituted isoxazoles undergo a cycloaddition reaction with dimethyl acetylenedicarboxylate across the C-4-C-5 bond to give 3,4-bis(methoxycarbonyl)pyridine derivatives.In a similar cycloadition of isoxazoles with methyl propiolate, 4-(methoxycarbonyl)pyridine derivatives were also obtained.The β-carbon atom of methyl propiolate could intervene in the bonding with the C-5 position of the isoxazoles regioselectively.A mechanism involving a complexed 2-oxa-3-azabicyclohepta-3,6-diene derivative and the subsequent N-Oand C-1-C-5 bond cleavage leading to a complexed (β-ketovinyl)nitrene intermediate is proposed for the formation of pyridine derivatives.In order to clarify the mechanistic aspect, the reaction of 4-phenyl-2-oxa-3-azabicyclohepta-3,6-diene and its related compounds were also studied to give pyridine derivatives.

Polystyrene-supported 2-bromoallyl sulfone as an efficient reagent for synthesis of 3,5-disubstituted isoxazoles

A facile method has been developed for the solid-phase organic synthesis of 3,5-disubstituted isoxazoles from polystyrene-supported 2-bromoallyl sulfone. The advantages of this method include a straightforward and convenient procedure, high product yield,

Asymmetric Aza-Diels-Alder Reactions of in Situ Generated β,β-Disubstituted α,β-Unsaturated N-H Ketimines Catalyzed by Chiral Phosphoric Acids

A novel asymmetric synthesis of dihydropyridinones with vicinal quaternary stereocenters has been realized by asymmetric aza-Diels-Alder reactions of 3-amido allylic alcohols with oxazolones enabled by chiral phosphoric acid catalysis. A series of aryl/alkyl- and alkyl/alkyl-disubstituted 3-amido allylic tertiary alcohols and 4-substituted oxazolones could be well tolerated in these reactions, producing dihydropyridinones with excellent diastereoselectivities and high enantioselectivities. Mechanistic study and control experiments were performed to shed light on the reaction mechanism, in which a configurationally defined β,β-disubstituted α,β-unsaturated N-H ketimine was proposed as the key intermediate.

Reaction of 1,3-Bis(het)arylmonothio-1,3-diketones with Sodium Azide: Regioselective Synthesis of 3,5-Bis(het)arylisoxazoles via Intramolecular N-O Bond Formation

An efficient new synthesis of 3,5-bis(het)arylisoxazoles, involving the reaction of 1,3-bis(het)arylmonothio-1,3-diketones with sodium azide in the presence of IBX catalyst, has been reported. The reaction proceeds at room temperature in high yields and is applicable to a broad range of substrates including the synthesis of 5-methyl-3-arylisoxazoles, a key subunit present in several β-lactamase-resistant antibiotics. A probable mechanism for the formation of isoxazoles has been suggested. A few of the 5-styryl/arylbutadienyl-3-(het)arylisoxazoles have also been synthesized by reacting the corresponding 1-(het)aryl-1-(methylthio)-4-(het)arylidene-but-1-en-3-ones with sodium azide at higher temperatures. The reaction of β-ketodithioesters with sodium azide is shown to furnish β-ketonitriles in good yields.

AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

The present invention relates to a novel compound, to a composition comprising the same, to methods for preparing the compound, and the use of this compound in therapy. In particular, the present invention relates to compound that is useful in the treatment and prevention of primary and secondary arterial hypertension, ictus, myocardial ischaemia, cardiac and renal insufficiency, myocardial infarction, peripheral vascular disease, diabetic proteinuria, Syndrome X and glaucoma.

Preparation method of isoxazole derivative

The invention relates to a preparation method of an isoxazole derivative, which comprises the following steps of mixing an propargyl alcohol derivative, a halogen source, an acid and a solvent, and heating to react; adding the hydroxylamine into the react