84965-95-7

Upstream product

• 111-66-0 oct-1-ene 
• 69054-15-5 N-(Trimethylsilyloxy)benzenecarboximidic Chloride 
• 932-90-1 Benzaldoxime 
• 873-67-6 benzonitrile oxide 
• 629-05-0 n-octyne 
• 495-18-1 Benzohydroxamic acid 
• 263888-04-6 O-tert-butyldiphenylsilyl benzhydroxamate 
• 100-52-7 benzaldehyde 
• 698-16-8 benzohydroximoyl chloride 

Downstream Products

• 118220-81-8 3-hydroxy-1-phenyldecane-1-one 
• 111-71-7 heptanal 
• 55563-72-9 3-methoxy-1-phenylpropan-1-one 
• 5650-41-9 3-hydroxy-1-phenylpropan-1-one 
• 98-86-2 acetophenone 
• 50-00-0 formaldehyd 

Relevant academic research and scientific papers

Aqueous phase preparation method of isoxazoline compound participating in vitamin E micro-micelle

The invention provides an aqueous phase synthesis method of the isoxazoline compound represented by the formula (III), wherein the benzaldehyde oxime represented by the formula (I) is a substrate, and the aqueous solution of the surfactant in the mass concentration 1 wt % - 5 wt % is N - chlorosuccinimide. Under the common action of the basic substance, the olefinic compound represented by the formula (II) is reacted 6 - 16h at room temperature, and the resulting reaction liquid is subjected to post-treatment to obtain the isoxazoline compound represented by the formula (III). Water serves as a reaction solvent, the use amount of the organic solvent is reduced, and zero emission of the solvent is realized.

Synthesis of 3,5-Disubstituted Isoxazoles through a 1,3-Dipolar Cycloaddition Reaction between Alkynes and Nitrile Oxides Generated from O-Silylated Hydroxamic Acids

In this paper, we report the regioselective synthesis of 3,5-disubstituted isoxazoles by 1,3-dipolar cycloaddition between alkynyl dipolarophiles and nitrile oxide dipoles generated in-situ from O-silylated hydroxamic acids in the presence of trifluoromethanesulfonic anhydride and NEt3. Thanks to the mild, metal-free and oxidant-free conditions that this strategy offers, the reaction was successfully applied to a wide variety of alkynyl dipolarophiles, demonstrating the tolerance of this approach to diverse functional groups. In particular, we have shown that the method was compatible with biological molecules such as peptides and peptide nucleic acids (PNA). This protocol constitutes another example of metal-free 1,3-dipolar cycloaddition leading to the regioselective formation of isoxazoles.

Hypervalent iodine catalyzed generation of nitrile oxides from oximes and their cycloaddition with alkenes or alkynes

Hypervalent iodine catalyzed oxidation of aldoximes using oxone as a terminal oxidant generates nitrile oxides, which react with alkenes and alkynes to give the corresponding isoxazolines and isoxazoles in moderate to good yields. This reaction involves active hypervalent iodine species formed in situ from catalytic iodoarene and oxone in the presence of hexafluoroisopropanol in aqueous methanol solution.

Hypoiodite mediated synthesis of isoxazolines from aldoximes and alkenes using catalytic KI and Oxone as the terminal oxidant

Isoxazolines can be efficiently synthesized in good yields via a hypoiodite mediated catalytic oxidative cyclization of aldoximes and alkenes. This reaction involves active iodine species generated in situ from catalytic amounts of KI and Oxone.

Generation of nitrile oxides from oximes using t -BuOI and their cycloaddition

tert-Butyl hypoiodite (t-BuOI) was found to be a powerful reagent for the cycloaddition of oximes and alkenes/alkynes, leading to the formation of a variety of isoxazolines or isoxazoles under mild conditions.

Conversion of oximes to carbonyl compounds by triscetylpyridinium tetrakis(oxodiperoxotungsto) phosphate (PCWP)-mediated oxidation with hydrogen peroxide

Aromatic and aliphatic oximes have been deoximated in chloroform-water to the corresponding aldehydes with dilute hydrogen peroxide and triscetylpyridinium tetrakis (oxodiperoxotungsto) phosphate as catalyst. The presence of dipolarophiles in the reaction mixtures allows a competitive reaction that converts oximes into isoxazole and isoxazoline derivatives via the intermediate formation of nitrile oxide species.

Chiral vinyl dioxazaborocines in synthesis: Asymmetric synthesis of 5- substituted Δ2-isoxazolines via nitrile oxide cycloaddition

Vinyl dioxazaborocines 1a-c have been subjected to 1,3-dipolar cycloadditions with benzonitrile oxide. The products are enantiomerically enriched 5-substituted Δ2-isoxazolines 2a-c.

Metal-carbonyl-induced Reaction of 2-Isoxazolines. Ring Cleavage and Reduction by Pentacarbonyliron or Nonacarbonyldi-iron

3,5-Disubstituted 2-isoxazolines (1a-f) undergo N-O and C-4 - C-5 bond-cleavage reaction with pentacarbonyliron and photoirradiation in methanol to give two fragments (aldehydes and ketones).The ketones could be derived from reduction of the complexed 1-substituted vinylnitrene intermediate and subsequent hydrolysis.Substituent effects have a significant influence on the course of the reaction. 2-Isoxazolines (1h and i) having no substituent at C-5 undergo N-O bond cleavage to give β-hydroxy- and β-methoxy-ketones, in addition to the above mentioned cleavage of the N-O and C-4 - C-5 bonds.Furthermore, 2-isoxazolines (1j and k) bearing a substituent such as an acetoxy or ethoxy group at C-5 undergo N-O bond cleavage, and concomitant elimination of the substituent acetoxy or ethoxy group, leading to β-aminoenones.However, in the case of 2-isoxazolines (1l and m) bearing a piperidin-1-yl group at C-5, the N-O and C-4 - C-5 bond-cleavage reactions predominate over the elimination of the C-5-substituent.Mechanisms are also proposed for the formation of the β-substituted ketones.Similar reactions were also effected thermally for several 2-isoxazolines with nonacarbonyldi-iron.