22020-72-0

Usage

InChI:InChI=1/C21H15NO/c1-4-10-16(11-5-1)19-20(17-12-6-2-7-13-17)22-23-21(19)18-14-8-3-9-15-18/h1-15H

Upstream product

• 873-67-6 benzonitrile oxide 
• 1215-07-2 (E)-(1-nitroethene-1,2-diyl)dibenzene 
• 622-42-4 1-nitro-1-phenylmethane 
• 15341-31-8 α-nitro-stilbene 
• 103161-67-7 2-benzoyl-1,2,3-triphenyl-propane-1,3-dione 
• 5452-30-2 3,4,5-triphenyl-4,5-dihydroisoxazole 2-oxide 
• 13286-95-8 meso-1,2-dinitro-1,2-diphenylethane 
• 100-52-7 benzaldehyde 
• 64-19-7 acetic acid 
• 17669-25-9 cis-4,5-dihydro-3,4,5-triphenylisoxazole 
• 65642-46-8 4-bromo-3,5,5-triphenyl-4,5-dihydro-isoxazole 
• 74048-22-9 3-nitro-1,2,3-triphenyl-2-propene-1-one 
• 7512-68-7 1,2,3-triphenyl-propenone oxime 
• 84940-63-6 triphenylisoxazoline-N-oxide 

Downstream Products

• 103-30-0 (E)-1,2-diphenyl-ethene 
• 854869-26-4 3-amino-1,2,3-triphenyl-propenone 
• 6624-55-1 benzil-mono-(O-benzoyl oxime ) 
• 80949-42-4 4-Chloro-5-methoxy-3,4,5-triphenyl-4,5-dihydro-isoxazole 
• 6237-59-8 hexamethyl benzenehexacarboxylate 
• 58329-12-7 dimethyl 2,5,6-triphenylpyridine-3,4-dicarboxylate 
• 80949-37-7 4-Chloro-3,4,5-triphenyl-4,5-dihydro-isoxazol-5-ol 
• 588-59-0 stilbene 
• 62-23-7 4-nitro-benzoic acid 
• 65-85-0 benzoic acid 
• 144-62-7 oxalic acid 
• 4888-39-5 1,2,3-triphenylpropane-1,3-dione 

Relevant academic research and scientific papers

A One Step Transformation of the Sodium Salt of α-aci-Nitrotoluene into 3,4,5-Triphenylisoxazole

3,4,5-Triphenylisoxazole was produced by the reaction of the sodium salt of α-aci-nitrotoluene with the 1-cyano-1-methylethyl radical.The reaction was found to proceed via one electron transfer from α-aci-nitrotoluene anion to a 1-cyano-1-methylethyl radi

Method for synthesizing 4-aryl isoxazole derivative

The invention belongs to the technical field of medicine and organic chemical industry, and discloses a method for synthesizing a 4-aryl isoxazole derivative. The method for synthesizing the 4aryl isoxazole derivative comprises the following steps: in a protective atmosphere, reacting O-benzyl alkyne ketoxime ether and a diarylether derivative in a solvent under the action of an alkaline compound and a palladium catalyst, and carrying out subsequent treatment to obtain the 4-aryl isoxazole derivative. The structure of the 4-aryl isoxazole derivative is shown as a formula I in the specification. According to the method, the 4-aryl isoxazole derivative is successfully synthesized, and raw materials of the method are low in price and easy to obtain, the operation is safe and simple, the functional group tolerance is high, the substrate universality range is wide, and the method has good in industrial application prospect.

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.

Copper-catalyzed aerobic oxidative C-O bond formation for the synthesis of 3,5-disubstituted isoxazoles from enone oximes

A direct access to 3,5-disubstituted isoxazoles has been accomplished through an intramolecular oxidative coupling reaction of enone oximes using a catalytic quantity of Cu(OAc)2. This method features an inexpensive metal catalyst, molecular ox

TEMPO-mediated aliphatic C-H Oxidation with Oximes and hydrazones

A method for aliphatic C-H bond oxidation of oximes and hydrazones mediated by 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) has been developed, which enables the concise assembly of substituted isoxazole and pyrazole skeletons.

Synthesis of isoxazoles by hypervalent iodine-induced cycloaddition of nitrile oxides to alkynes

Treatment of oximes with hypervalent iodine leads to substituted isoxazoles via rapid formation of nitrile oxides. Reaction with terminal alkynes led to a series of 3,5-disubstituted isoxazoles with complete regioselectivity and high yield, in a procedure

Stereospecific approach to α,β-disubstituted nitroalkenes via coupling of α-bromonitroalkenes with boronic acids and terminal acetylenes

(Z)-α-Bromo-β-substituted nitroethylenes undergo facile Suzuki coupling with aryl, heteroaryl, and vinylboronic acids in the presence of Pd(PPh3)4 as catalyst to afford (E)-α,β-disubstituted nitroethylenes in high yield (up to 95%) and complete specificity. Similar coupling of α-bromonitroethylenes with terminal acetylenes (Sonogashira coupling) provides a novel route to (E)-nitroenynes. These Pd-catalyzed coupling methods offer a convenient and stereospecific entry into a diverse array of synthetically and biologically useful α,β-disubstituted nitroethylenes.

Free radicals trapping reactions with 3,5-di-t-butyl-nitrosobenzene. The Α-nitrobenzyl free radical

The reactions of sodium and potassium phenylnitrolates (the salts of aci-phenylnitromethane) with iodine, studied by Nenitzescu in 1929,1 were reinvestigated in order to detect the α-nitrobenzyl free radical. In agreement with Nenitzescu we confirmed that only (±)-α,α′-dinitrodibenzyl (m.p. 150°) resulted on treating the salts with iodine at 0-5°. The meso modification (m.p. 236-237°) does not seem to be formed in any reaction conditions used either by Nenitzescu or by us in this work. Addition of an iodine crystal to a suspension of sodium phenylnitrolate in dry benzene and immediate recording of the ESR spectrum allowed the observation of a nitrogen free radical (aN = 0.458 mT; g = 2.0058), not agreeing with the structure of the simple α-nitrobenzyl free radical. Dry potassium pbenylnitrolate kept in a dry air atmosphere is transformed in 3,4,5-triphenylisoxazole. Possible structures for the observed radical and the pathway leading to its formation are discussed in relation to trans-stilbene formation.

UNSYMMETRICAL CONNECTIVE OLEFINATION BY KORNBLUM NITRO-SYNTHESIS : APPLICATIONS IN PHYTUBERIN CHEMISTRY

Kornblum unsymmetrical olefin synthesis employing radical-anion chain crossed-coupling (light catalysed) of a mono- and a gem-di-nitro-compound, followed by reductive NO2 removal, is examined in the context of a hindered olefin structure required for phytuberin synthesis.Whilst successful for a tetrasubstituted olefin model (for which a Witting approach failed), increasing substitution on the β-position of the mono-nitro component supressed the coupling reaction, presumably for steric reasons.An alternative coupling involving a bromonitrocyclohexane and a mononitroacetal caused symmetrical coupling of the mononitro-component in high yield, rather than a crossed reaction.Reductive elimination (using Na2S/DMF) from either rac.- or meso- 1,2-dinitro-1,2-diphenylethane leads to (E)-stilbene 98percent (E) > probably through a stabilised radical or anion.A convenient preparation of triphenylisoxazoline-N-oxide is reported.