1148-87-4

Usage

Uses

Used in Pharmaceutical Development:
Isoxazole, 5-(4-chlorophenyl)-3-phenyl-, is utilized as a key intermediate in the synthesis of new drugs, particularly those targeting various therapeutic areas. Its unique structure allows for the development of compounds with specific biological activities, making it a promising candidate for medicinal chemistry.
Used in Scientific Research:
Isoxazole, 5-(4-chlorophenyl)-3-phenylserves as a valuable tool in scientific research, where it can be used to study the effects of structural modifications on biological activity. It can also be employed to investigate the mechanisms of action of drugs and to understand the interactions between drugs and their targets.
Used in Chemical Analysis:
Isoxazole, 5-(4-chlorophenyl)-3-phenyl-, can be used as a reference standard in chemical analysis, ensuring the accuracy and reliability of analytical methods. Its well-defined structure and properties make it suitable for calibrating instruments and validating analytical techniques.
Used in Drug Synthesis:
In the pharmaceutical industry, Isoxazole, 5-(4-chlorophenyl)-3-phenyl-, is used as a building block for the creation of new drug molecules. Its incorporation into drug candidates can potentially enhance their efficacy, selectivity, and pharmacokinetic properties, leading to the development of more effective therapeutic agents.
Used in Medicinal Chemistry:
As a component of medicinal chemistry, Isoxazole, 5-(4-chlorophenyl)-3-phenyl-, is employed in the design and optimization of drug candidates. Its unique structural features can be leveraged to improve the potency, selectivity, and safety profiles of new drugs, contributing to the advancement of therapeutic options for various diseases and conditions.

InChI:InChI=1/C15H10ClNO/c16-13-8-6-12(7-9-13)15-10-14(17-18-15)11-4-2-1-3-5-11/h1-10H

Upstream product

• 623-03-0 4-Cyanochlorobenzene 
• 613-91-2 acetophenone oxime 
• 856332-21-3 5-(4-chloro-phenyl)-3-phenyl-4,5-dihydro-isoxazol-4-ol 
• 17059-59-5 1-(4-chloro-phenyl)-3-phenyl-propane-1,3-dione 
• 5739-39-9 3-(4-chlorophenyl)-1-phenylpropan-1-one 
• 29776-35-0 1-(4-chlorophenyl)-3-phenylprop-2-yn-1-one 
• 98-88-4 benzoyl chloride 
• 873-73-4 4-n-chlorophenylacetylene 
• 122-01-0 4-chloro-benzoyl chloride 
• 532-27-4 1-chloroacetophenone 
• 1679-18-1 4-Chlorophenylboronic acid 
• 454253-30-6 trifluoromethanesulfonic acid 3-phenyl-isoxazol-5-yl ester 
• 1076-59-1 3-phenyl-4H-isoxazol-5-one 
• 24721-26-4 4-chlorochalcone 

Downstream Products

• 31554-60-6 4-chloro-5-(4-chlorophenyl)-3-phenylisoxazole 
• 80223-13-8 5-(4-Chloro-phenyl)-2-methyl-3-phenyl-isoxazol-2-ium; iodide 

Relevant academic research and scientific papers

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

One-pot regioselective synthesis of substituted pyrazoles and isoxazoles in PEG-400/water medium by Cu-free nano-Pd catalyzed sequential acyl Sonogashira coupling-intramolecular cyclization

Catalyst efficacy of in situ generated Pd-nanoparticles (PdNPs) in the regioselective one-pot synthesis of 3,5-di & 3,4,5-trisubstituted pyrazoles and 3,5-disubstituted isoxazoles in environmentally benign PEG-400/H2O medium, which involves the sequential (i) Cu-free acyl-Sonogashira coupling (ASC) and (ii) intramolecular ynone-amine cyclization under PTC conditions was described. The results of controlled experiments support the operation of two sequential catalytic cycles (ASC/cyclization) and achievement of complementary/opposite regioselectivity via ynone-bound palladium in a one-pot approach. Moreover, the in situ PdNPs recovered after the first catalytic cycle of the one-pot reaction sequence have been reused again five times successively. Besides, prior to the above studies, the efficacy of some common Pd-N-heterocyclic carbene (Pd-NHC) complexes in catalyzing the same one-pot two-step reaction sequence (Cu-free ASC/cyclization) both in water and organic solvents was also optimized. In situ generation of PdNPs from above Pd-NHCs in water was also identified, but they are not reusable due to their large size distribution.

An Intramolecular Wittig Approach toward Heteroarenes: Synthesis of Pyrazoles, Isoxazoles, and Chromenone-oximes

α-Halohydrazones/ketoximes are transformed into trisubstituted pyrazoles/disubstituted isoxazoles by treatment with phosphine, acyl chloride, and a base. Mechanistic investigations revealed the in situ formation of azo/nitroso olefin intermediates which underwent a tandem phospha-Michael/N- or O-acylation/intramolecular Wittig reaction to afford the heteroarenes in moderate to good yields. Further, proper functionalization of α-haloketoximes and a change of conditions allowed the chemoselective synthesis of chromenone-oximes as well as rearranged isoxazoles, thereby realizing a diversity-oriented synthesis.

General Platform for the Conversion of Isoxazol-5-ones to 3,5-Disubstituted Isoxazoles via Nucleophilic Substitutions and Palladium Catalyzed Cross-Coupling Strategies

A general platform for the conversion of isoxazol-5-ones to 3,5-disubstituted isoxazoles has been developed via a two-step strategy. The first step leads to the formation of 5-(pseudo)halogenated isoxazoles, while in the second, a variety of heteroalkyl-, heteroaryl-, alkyl-, alkenyl-, alkynyl- and aryl-chains can be installed via nucleophilic substitutions or palladium catalyzed cross-coupling reactions.

A convenient one-pot synthesis of 3,5-diarylisoxazoles via oxidative cyclisation using catalytic CuBr2 and oxone

A facile one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones and hydroxylamine hydrochloride is reported. The reaction is efficiently promoted by catalytic CuBr2 and Oxone to afford the desired products mostly in high yields

Trichloroisocyanuric acid mediated one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones

A facile one-pot synthesis of 3,5-diarylisoxazoles from α,β-unsaturated ketones and hydroxylamine hydrochloride is reported. The reaction is efficiently promoted by trichloroisocyanuric acid (TCCA) to afford the desired products, mostly in high yields and

Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization

A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C-N and C-O bonds and intermolecular C-C bonds from aromatic alkenes or alkynes and N -hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C-H and C-C bonds/construction of C-O bonds/elimination of SO 2 /C-N bond formation is achieved in sequence in the reaction system.

TBAI-catalyzed intramolecular annulation of chalcone oximes toward isoxazoles

A TBAI-catalyzed intramolecular annulation of chalcone oximes toward isoxazoles was developed, providing 3,5-diarylisoxazoles in good yields. Functional groups such as methoxy, ethyoxyl, chloro, bromo, fluoro and nitro were well tolerated in this reaction

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

Preparation of 3,5-disubstituted pyrazoles and isoxazoles from terminal alkynes, aldehydes, hydrazines, and hydroxylamine

The reaction of terminal alkynes with n-BuLi, and then with aldehydes, followed by the treatment with molecular iodine, and subsequently hydrazines or hydroxylamine provided the corresponding 3,5-disubstituted pyrazoles or isoxazoles in good yields with high regioselectivity, through the formations of propargyl secondary alkoxides and α-alkynyl ketones. The present reactions are one-pot preparation of 3,5-disubstituted pyrazoles from terminal alkynes, aldehydes, molecular iodine, and hydrazines, and 3,5-disubstituted isoxazoles from terminal alkynes, aldehydes, molecular iodine, and hydroxylamine.