1037-05-4

Basic information

• Product Name: Isoxazole, 4,5-dihydro-5-(2-naphthalenyl)-3-phenyl-
• CAS NO: 1037-05-4
• Molecular Formula: C19H15NO
• Molecular Weight: 273.334
• Mol File: 1037-05-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Isoxazole, 4,5-dihydro-5-(2-naphthalenyl)-3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 4,5-dihydro-5-(2-naphthalenyl)-3-phenyl-(1037-05-4)
• EPA Substance Registry System: Isoxazole, 4,5-dihydro-5-(2-naphthalenyl)-3-phenyl-(1037-05-4)

Safety Data

• Hazardous Substances Data: 1037-05-4(Hazardous Substances Data)

Upstream product

• 827-54-3 2-naphthylethylene 
• 156605-56-0 1-phenylethan-1-one O-pivaloyl oxime 
• 66-99-9 β-naphthaldehyde 
• 611-73-4 Benzoylformic acid 
• 25327-36-0 (Z)-2-(hydroxyimino)-2-phenylacetic acid 
• 932-90-1 Benzaldoxime 

Downstream Products

• 1106719-26-9 (S)-5-(2-naphthyl)-3-phenyl-2-isoxazoline 
• 1106719-24-7 (3S,5S)-trans-N-benzoyl-5-(2-naphthyl)-3-phenylisoxazolidine 
• 1106719-22-5 (3S,5R)-cis-N-benzoyl-5-(2-naphthyl)-3-phenylisoxazolidine 

Relevant articles and documents

Heteroannulation of Alkenes with Enynyl Benziodoxolones and Silver Nitrite Involving CC bond Oxidative Cleavage: Entry to 3-Aryl-?2-isoxazolines

A copper-catalyzed [2 + 2 + 1] heteroannulation of alkenes with enynyl benziodoxolones and AgNO2 involving oxidative cleavage of the CC bond promoted by cooperative Zn(OTf)2, KOAc, and 4 ? MS for producing 3-aryl δ2-isoxazolines is reported. Mechanistic s

3,4,5-trisubstituted-4,5-dihydroisoxazole, derivative and synthetic method and application thereof

The invention relates to 3,4,5-trisubstituted-4,5-dihydroisoxazole, a derivative and a synthetic method and an application thereof. The invention mainly relates to a synthetic method of an isoxazoline compound. With adoption of a technical scheme that an aldehyde compound and oxime ester are converted into isoxazoline and the derivative thereof by taking an organic solvent as a solvent under the action of alkali without using a catalyst, the synthetic method solves the problem that an existing synthetic method of the isoxazoline compound is complicated in synthetic step, is accomplished by adopting multiple steps, and also needs a metal catalyst, a chemically equivalent metal oxidant or a peroxide. The atom economy is kept to the extreme extent; the isoxazoline compound has a stable molecular structure and an excellent chemical property, and molecular slices and compound segments contain rich contents with biological activity and pharmacological activity. The isoxazoline compound also has the characteristics of being simple in reaction system, mild in reaction condition, relatively less in reaction equipment, simple in experimental operation, wide in source of materials, high in yield, easy for expansion of user and application, relatively high in utilization value of product and expectable in market commercial prospect.

Asymmetric reduction of racemic 2-isoxazolines

The kinetic resolution of racemic 2-isoxazolines was carried out by asymmetric reduction using borane with 1,2-amino alcohols as a chiral source. Using excess BH3-THF in the presence of (-)-norephedrine, optically active 1,3-amino alcohol derivatives were obtained with good ee but in lower yield, while the optically active substrates 2-isoxazolines were recovered with modest ee. The asymmetric reduction using 2.0 equiv of BH3-SMe2 was investigated as an alternative strategy for the synthesis of optically active products. After reduction, treatment of the resulting mixture with Et3N was successful in providing optically active isoxazolidine derivatives in good yields and with good ee. The choice of chiral source was also shown to have a significant effect. In particular, the use of (S)-α,α-diphenyl-2-pyrrolidinemethanol reversed the enantioselectivity of the recovered substrates.