55086-61-8

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
1-(3-Methyl-5-Isoxazolyl) Ethanone is utilized as a key intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of new compounds with potential therapeutic and pesticidal properties, contributing to advancements in healthcare and agriculture.
Used in the Food Industry:
In the food industry, 1-(3-Methyl-5-Isoxazolyl) Ethanone serves as a flavoring agent, imparting a nutty and fruity aroma to a variety of products. Its ability to enhance the sensory experience of food items makes it a valuable ingredient in the creation of diverse flavors.
Used in Organic Chemistry Research:
1-(3-Methyl-5-Isoxazolyl) Ethanone also holds potential in the field of organic chemistry as a reagent or intermediate in the preparation of complex organic compounds. Its unique chemical structure facilitates the synthesis of novel molecules, driving innovation and discovery in chemical research.

InChI:InChI=1/C6H7NO2/c1-4-3-6(5(2)8)9-7-4/h3H,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 70753-36-5 3-methylisoxazole-5-carbaldehyde 
• 7064-09-7 5-isopropenyl-3-methyl-isoxazole 
• 62260-34-8 hex-3-ene-2,5-dione dioxime 
• 71502-43-7 (3-methyl-5-isoxazolyl)-1-ethanol 
• 17492-61-4 1-(3-methyl-4,5-dihydro-isoxazol-5-yl)-ethanone 
• 14716-89-3 3-methyl-5-isoxazolemethanol 
• 138958-55-1 2-(3-methyl-5-isoxazolyl)-2-propanol 
• 63366-79-0 3-methylisoxazole-5-carboxylic acid ethyl ester 
• 683-58-9 1-chloro-1-(N-hydroxyimino)ethane 
• 1423-60-5 methyl ethynyl ketone 

Downstream Products

• 61858-87-5 [1-(3-methyl-isoxazol-5-yl)-ethyl]-triphenyl-phosphonium; bromide 
• 138958-56-2 1-(3-methyl-5-isoxazolyl)-1-phenyl-1-ethanol 
• 138958-57-3 1-(4-fluorophenyl)-1-(3-methyl-5-isoxazolyl)-1-ethanol 
• 104777-32-4 2-bromo-1-(3-methyl-1,2-oxazol-5-yl)ethanone 
• 71502-43-7 (3-methyl-5-isoxazolyl)-1-ethanol 
• 133255-53-5 2,5-dimethyl-2-phenyl-3(2H)-furanone 
• 138958-49-3 (E)-2-methyl-2-phenyl-5-[2-(thien-3-yl)ethenyl]-3(2H)-furanone 
• 138958-47-1 2-phenyl-2-methyl-5-[2-(3-pyridinyl)ethenyl]-3(2H)-furanone 
• 138958-48-2 2-Methyl-2-phenyl-5-((E)-2-pyridin-4-yl-vinyl)-furan-3-one 
• 138958-46-0 2-methyl-2-phenyl-5-[2-(2-pyridinyl)ethenyl]-3(2H)-furanone 
• 138958-50-6 4-[(E)-2-(5-Methyl-4-oxo-5-phenyl-4,5-dihydro-furan-2-yl)-vinyl]-benzonitrile 
• 138958-53-9 (E)-2-(4-fluorophenyl)-2-methyl-5-[2-(thien-3-yl)ethenyl]-3(2H)-furanone 
• 138958-52-8 2-methyl-2-(4-fluorophenyl)-5-[2-(2-pyridinyl)ethenyl]-3(2H)-furanone 
• 138958-51-7 4-[2-[2,3-Dihydro-2-(4-fluorophenyl)-2-methyl-3-oxo-5-furanyl]ethenyl]benzonitrile 

Relevant academic research and scientific papers

ALKYNYL ALCOHOLS AS KINASE INHIBITORS

Selected compounds are effective for prophylaxis and treatment of inflammation and inflammatory disorders, such as NIK-mediated disorders. The invention encompasses novel compounds, analogs, prodrugs and pharmaceutically acceptable salts thereof, pharmaceutical compositions and methods for prophylaxis and treatment of diseases and other maladies or conditions involving, inflammation and the like.

Ab initio analysis on metal ion catalysis in the enolization reactions of some acetylheterocycles: Kinetics of the enolization reactions of 3-acetyl-5-methylisoxazole, 5-acetyl-3-methylisoxazole and 3(5)-acetylpyrazole

Kinetic data on the enolization reaction of 3-acetyl-5-methylisoxazole, 5-acetyl-3-methylisoxazole, 3(5)-acetylpyrazole and some previously studied acetylheterocycles have been the object of a comprehensive ab initio analysis. Enolization rate constants were measured spectrophotometrically by the halogen trapping technique at 25 °C and ionic strength of 0.3 mol dm-3 in water, in acetate buffers, in dilute hydrochloric acid, in dilute sodium hydroxide and in the presence of some metal ion salts. In the spontaneous (water) and base (acetate) catalysed reactions the ketones investigated are generally more reactive than acetophenone, according to the electron-withdrawing effect of the heterocyclic ring compared with the benzene ring. In particular, acetylisoxazoles, 3(5)-acetylpyrazole and acetylthiazoles are more reactive than acetylfurans, 2-acetylpyrrole and acetylthiophenes respectively, and this can be attributed to the additional effect of the second heteroatom in the heterocyclic moiety. On the other hand, the compounds investigated are generally less reactive than acetophenone in the H3O+ -catalysed reaction. Ab initio calculations on the relative stability of the protonated and unprotonated forms of the substrates investigated have been compared with the kinetic results obtained in acid solutions. As far as the metal ion catalysis is concerned, an approach in terms of ΔΔE can give an estimate of the combined contributions of charge densities and frontier orbitals to the interaction of the substrate with the metal ion catalyst. A comparison of experimental metal activating factor values and ab initio calculations outlines the importance of charge density on the carbonyl oxygen atom of acetylheterocycles with one heteroatom. An analogous comparison for acetylheterocycles with two heteroatoms suggests the formation of a chelate complex or transition state, in which the metal ion coordinates both the carbonyl oxygen and the aza nitrogen, whenever these two atoms are suitably placed within the molecular structure of the acetylheterocycle. Copyright

Synthesis and pharmacological characterization of new analogs of broxaterol

A series of isoxazole derivatives structurally related to broxaterol 1 has been prepared and tested for their potency to β1 and β2 adrenergic receptors. At variance with broxaterol, none of the tested compounds displayed agonistic activity. The 3-isopropenyl derivative 5f is the most potent antagonist both in the trachea and atria preparations.

Regioselective synthesis of 4-acetyl- and 5-acetyl-3-methylisoxazole: Their conversion into silyl- and methyl enol ethers

Acetonitrile oxide reacts regioselectively with 3-buten-2-one and (E)-4-methoxy-3-buten-2-one to give 5-acetyl- 2 and 4-acetyl-3-methylisoxazole 3, respectively. Treatment of ketones 2 and 3 with trimethylsilyl trifluoromethanesulfonate gave the silyl enol ethers 4 and 5, whereas the methyl enol ethers 8 and 9 were obtained via elimination of methanol from the corresponding dimethyl ketals.

Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)- furanones

In order to investigate new antiulcer agents, spizofurone 1 (AG-629) was fragmented and reassembled to generate 5-phenyl-2,2-dimethyl-3(2H)-furanone (bullatenone, 2). Because of the antiulcer activity of 2,5-phenyl-substituted 2,2-dimethyl-3(2H)-furanones (3-6) were made and shown to have poor activity. Insertion of an ethenyl link between the furanone and phenyl rings gave 5-(2- phenylethenyl)-2,2-dimethyl-3(2H)-furanone (7). This compound had better activity than 2. Compounds 8-41 were synthesized to evaluate the SAR in 5-(2- ethenyl substituted)-3(2H)-furanones. Electron-withdrawing substituents on the aromatic ring (8, 10, 19, and 20) gave 2-3-fold higher activity. Further increases in the activity were found when the phenyl ring was replaced by heterocyclic nuclei. Compounds that contained a thiophene (29), pyridine (24- 26), or quinoline ring (32) had the best activity. Replacement of the methyl group on the furanone ring with a phenyl (34) or p-fluorophenyl (40) substituent in the 2-pyridine series gave compounds with activity that ranked with the best obtained in this study. The best compounds from the above SAR studies were evaluated in the ethanol-necrosis model for duration of cytoprotection action. Compounds 19, 24, and 29, which had the best duration of action, were tested with AG-629 in the acidified aspirin and indomethacin- induced lesion models. Only compound 24 had equivalent activity with AG-629 in both models.

Chemoenzymatic Synthesis of Chiral Isoxazole Derivatives

The synthesis of the two enantiomers of 1-(3-bromo-5-isoxazolyl)-2-(tert-butylamino)ethanol (1), a potent and selective β2-adrenergic stimulant, has been efficiently accomplished by enzyme-catalyzed transformations.The absolute configurations are attributed to (+)- and (-)-1 by correlation with (S)-3-butyn-2-ol.The S enantiomer was prepared in >98percent enantiomeric excess by reducing α-bromo ketone 4 in the presence of alcohol dehydrogenase from Thermoanaerobium brockii and the R enantiomer was obtained in 97percent ee through a kinetic resolution of the racemic bromohydrin(+/-)-5, in organic solvents, catalyzed by lipase P from Pseudomonas fluorescens.The experimental conditions for the lipase-catalyzed asymmetric transesterifications were optimized in order to improve reaction rates and the enantiomeric excess of the products.