4894-23-9

Usage

Uses

Used in Pharmaceutical Industry:
3,5-Diphenyl-2-isoxazoline is used as a key building block for the synthesis of various pharmaceuticals due to its unique structural and chemical properties. It contributes to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, 3,5-Diphenyl-2-isoxazoline serves as a crucial component in the synthesis of agrochemicals, helping to create effective pesticides and other agricultural products to protect crops and enhance yields.
Used in Material Science:
3,5-Diphenyl-2-isoxazoline is used as a component in the development of advanced polymers and liquid crystals. Its ability to form stable and complex molecular structures makes it a valuable asset in material science, contributing to the creation of innovative materials with diverse applications.
Used as an Antiproliferative Agent:
3,5-Diphenyl-2-isoxazoline has been studied for its potential biological activities, including its use as an antiproliferative agent against cancer cells. This property makes it a promising candidate for further research and development in oncology.
Used as an Anti-inflammatory Agent:
Additionally, 3,5-Diphenyl-2-isoxazoline has shown potential as an anti-inflammatory agent, which could be beneficial in the treatment of various inflammatory conditions and diseases. Further research is needed to explore its full potential in this area.

InChI:InChI=1/C15H13NO/c1-3-7-12(8-4-1)14-11-15(17-16-14)13-9-5-2-6-10-13/h1-10,15H,11H2

Upstream product

• 100-42-5 styrene 
• 873-67-6 benzonitrile oxide 
• 60-29-7 diethyl ether 
• 98-81-7 1-bromovinylbenzene 
• 32831-01-9 3-chloro-3-phenylpropiophenone 
• 698-16-8 benzohydroximoyl chloride 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 622-42-4 1-nitro-1-phenylmethane 
• 20141-73-5 benzaldehyde oxime O-tributylstannyl ether 
• 108199-02-6 O-ethoxycarbonylbenzohydroximoyl chloride 
• 1138-48-3 cis-1,2-diphenylcyclopropane 
• 1138-47-2 trans-1,2-diphenylcyclopropane 
• 70367-29-2 3-benzenesulfonyl-5-phenyl-4,5-dihydro-isoxazole 
• 591-51-5 phenyllithium 

Downstream Products

• 36879-72-8 4,5-diphenyl-3-oxazoline 
• 2039-49-8 3,5-diphehylisoxazole 
• 5371-55-1 1-hydroxyimino-1,3-diphenylpropane 
• 25756-02-9 erythro-3-amino-1,3-diphenylpropanol 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 42052-51-7 3-hydroxy-1,3-diphenylpropan-1-one 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 94-41-7 benzalacetophenone 
• 13286-60-7 (±)-3-amino-1,3-diphenylpropan-1-ol 
• 13286-60-7 (±)-3-amino-1,3-diphenylpropan-1-ol 
• 211998-03-7 (R)-3,5-diphenyl-2-isoxazoline 
• 441788-62-1 (1R,3S)-3-amino-1,3-diphenylpropan-1-ol 
• 13286-60-7 (1S,3R)-3-amino-1,3-diphenyl-propan-1-ol 

Relevant academic research and scientific papers

Gold-Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence of O-Propargylic Oximes Derived from Glyoxylates

We successfully extended our gold-catalyzed skeletal rearrangement reaction of O -propargylic oximes through C=N bond cleavage to include substrates having an ester group on the oxime moiety, affording the corresponding 2-isoxazolines having an alkoxycarb

Nickel(II)-Catalyzed Oxygen Transfer Reaction of N-Vinyl Nitrones to Prepare 2-(Pyridin-2-yl)ethanols

A nickel(II)-catalyzed oxygen transfer reaction of dibenzylideneacetone-derived N-vinyl-α,β-unsaturated nitrones has been identified for the preparation of polysubstituted 2-(pyridin-2-yl)ethanols in good yields with high atom economy. The scope of the method is described, and mechanistic experiments are discussed. The reaction was easily performed at gram scales, and pyrido[2,3-c]carbazole was obtained in moderate yield over three steps.

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.

TEMPO-Mediated Selective Synthesis of Isoxazolines, 5-Hydroxy-2-isoxazolines, and Isoxazoles via Aliphatic δ-C(sp3)-H Bond Oxidation of Oximes

Selective synthesis of three different bioactive heterocycles; isoxazolines, 5-hydroxy-2-isoxazolines and isoxazoles from the same starting material using TEMPO (2,2,6,6-Tetramethylpiperidin-1-oxyl) as a radical initiator is reported. Selectivity was achi

Synthesis of 2-Isoxazoline N-Oxides by Copper-Mediated Radical Annulation of Alkenes with α-Nitrobenzyl Bromides

Copper-mediated [3 + 2] annulation of alkenes with α-nitrobenzyl bromides has been developed. The reaction is promoted simply by a copper salt to produce the corresponding 2-isoxazoline N-oxides with perfect regioselectivity. The present method can be conducted under mild conditions, affording a diverse array of 2-isoxazoline N-oxides. The obtained products can readily be converted to the related heterocycles such as 2-isoxazoline and isoxazole. A radical-polar crossover pathway initiated by single-electron transfer from nitronate to a copper salt is proposed.

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

Study of the Features of the Reaction of Arylcyclopropanes with Nitrozonium Ethyl Sulfate or Nitrozonium Tetrafluoroborate

Abstract: The reactions of diaryl-, aryl-, and alkyl–arylcyclopropanes with ethyl nitrite in the presence of sulfur trioxide and sulfur trioxide dioxane complex, as well as the reactions of 1-alkyl-2-arylcyclopropanes with NOBF4 were studied. It was found that the attack of the nitrosonium cation, accompanied by the formation of a benzyl carbocation, leads to the formation of isoxazolines. The introduction of bulky alkyl substituents into the cyclopropane ring changes the regioselectivity of nitrosation, favoring the attack of the electrophilic particle on the benzyl position and leading to the competitive formation of an alkyl carbocation. Depending on the structure of the alkyl substituent, both products of intramolecular heterocyclization accompanied by skeletal rearrangements and products formed with the participation of an external nucleophile are formed.

Nitrosylsulfuric acid as a tandem reagent in the synthesis of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes

It was demonstrated that nitrosylsulfuric acid can be successfully used as a tandem nitrosating and oxidizing agent in the synthesis of 3,5-diarylisoxazoles from 1,2-diarylcyclopropanes. The reaction proceeds highly regioselectively in the case of symmetr

Iron(iii)-catalyzed selective N-O bond cleavage to prepare tetrasubstituted pyridines and 3,5-disubstituted isoxazolines from: N -vinyl-α,β-unsaturated ketonitrones

An iron(iii)-catalyst controlled cyclization and selective N-O bond cleavage of N-vinyl-α,β-unsaturated nitrones has been achieved under mild conditions to access tetrasubstituted pyridines and 3,5-disubstituted isoxazolines in moderate to good yields. The tetrasubstituted pyridines were afforded with FeCl3 as a catalyst while using FeCl3·6H2O combined with 1,10-phenanthroline delivered isoxazolines. The regioselectivity for cyclization of styrenyl groups in N-vinyl-α,β-unsaturated nitrones was completely different during the formation of pyridines and isoxazolines. A rational mechanism for the formation of pyridines and isoxazolines was proposed based on the further control experimental studies. The isoxazolines can be converted to a novel bidentate N-ligand over four steps and an epoxypyridine scaffold was obtained from N-vinyl nitrone when copper(ii) acetate in combination with the prepared bidentate N-ligand was used.

Structural and morphological aspects of small 3,5-disubstituted isoxazoles

The structural and morphological features of small 3,5-disubstituted isoxazoles/isoxazolines are presented and discussed in the light of thermal analysis by differential scanning calorimetry (DSC), polarized optical microscopy (POM) technique, combined with single crystal X-ray diffraction and molecular modeling. The title compounds obtained were also characterized by 1H, 13C and 19F NMR. Two of the 3,5-diarylisoxazoles reported here contain totally hydrogenated or fluorinated benzene rings on both sides of the heterocycle. Partially hydrogenated and fluorinated molecules were prepared alternating the position of the benzene rings on 3- and 5-position of the isoxazoles. Other isoxazoles were synthesized to compare the influence of fluorine atoms on the transitional properties. They were synthesized in two steps, starting from [3 + 2] 1,3-dipolar cycloaddition reaction of nitrile oxides with alkenes to yield the isoxazolines and subsequent MnO2-oxidation process to reach the final isoxazoles.