1777-53-3

Usage

Uses

Used in Organic Synthesis:
Ethanone, 1-(4-methylphenyl)-2-(triphenylphosphoranylidene)is utilized as a reagent in organic synthesis for its unique chemical reactivity. The presence of the ketone and phosphoranylidene groups allows it to participate in the formation of carbon-carbon double bonds, which is crucial for creating new organic molecules with specific properties and functions.
Used in Catalysis:
In the field of catalysis, Ethanone, 1-(4-methylphenyl)-2-(triphenylphosphoranylidene)serves as a catalyst or a catalyst precursor, particularly in reactions involving phosphorus-containing compounds. Its ability to facilitate or enhance the rate of chemical reactions without being consumed in the process makes it a valuable asset in various industrial applications.
Further Research:
Ethanone, 1-(4-methylphenyl)-2-(triphenylphosphoranylidene)is a subject of ongoing research to explore its full potential and uncover additional specific uses and properties. As our understanding of Ethanone, 1-(4-methylphenyl)-2-(triphenylphosphoranylidene)- grows, it may find its way into new applications across different industries, such as pharmaceuticals, materials science, or environmental chemistry, where its unique reactivity could be harnessed to solve complex challenges.

Upstream product

• 2689-61-4 (2-oxo-2-p-tolylethyl)triphenylphosphonium bromide 
• 13222-85-0 p-methylbenzoic anhydride 
• 3739-97-7 (trimethylsilyl)methylenetriphenylphosphorane 
• 53358-36-4 trimethylsilyl p-methylbenzoate 
• 874-60-2 4-methyl-benzoyl chloride 
• 19493-09-5 Methylenetriphenylphosphorane 
• 619-41-0 4-(bromoacetyl)toluene 
• 603-35-0 triphenylphosphine 
• 25850-59-3 [(4-methylbenzoyl)(phenylthiocarbamoyl)methylene]triphenylphosphorane 
• 3739-98-8 triphenyl(trimethylsilylmethyl)phosphonium iodide 
• 122-00-9 para-methylacetophenone 

Downstream Products

• 55210-72-5 (E)-3-(3,5-Dichloro-2-hydroxy-phenyl)-1-p-tolyl-propenone 
• 2227-58-9 3-(4-methylphenyl)prop-2-ynoic acid 
• 91585-31-8 phenyl(p-tolylethynyl)selane 
• 20972-36-5 4-(p-methylphenyl)-4-oxo-2-butenoic acid 
• 1190719-40-4 (E)-4-((1-methyl-1H-indol-2-yl)methoxy)-1-p-tolylbut-2-en-1-one 
• 1189060-11-4 ethyl (E,E)-6-(4-methylphenyl)-6-oxohexa-2,4-dienoate 
• 1267589-04-7 (E)-2-(2-(3-oxo-3-(4-methylphenyl)prop-1-en-1-yl)phenoxy)acetic acid 
• 1267588-85-1 (E)-3-(2-(3-oxo-3-(4-methylphenyl)prop-1-en-1-yl)phenyl)propanoic acid 
• 1267587-91-6 (4aR, 9aR)-3-(4-methylphenyl)-9,9a-dihydroindeno[2,1-c]pyran-1(4aH)-one 
• 1267588-02-2 (1R,2R)-N-isopropyl-1-(2-oxo-2-(p-tolyl)ethyl)-2,3-dihydro-1H-indene-2-carboxamide 
• 1267588-11-3 (2R,3S)-methyl-3-(2-oxo-2-(p-tolyl)ethyl)-2,3-dihydrobenzofuran-2-carboxylate 
• 19832-78-1 1-(4-methylphenyl)prop-2-en-1-one 
• 1256284-88-4 2-(9-methyl-2,3,4,9-tetrahydro-1H-carbazol-4-yl)-1-p-tolylethanone 
• 1256284-98-6 2-(5,9-dimethyl-2,3,4,9-tetrahydro-1H-carbazol-4-yl)-1-p-tolylethanone 

Relevant academic research and scientific papers

New mercury(II) and cadmium(II) complexes with (p-methylbenzoyl)methylene triphenylphosphorane: Synthesis, spectroscopic and structural characterization

Reaction of Ph3PCHCOC6H4Me (L), with HgX2 and CdCl2·H2O in methanol with equimolar ratios give binuclear complexes of the type [MX(μ-X){CH(PPh 3)C(O)C6H4Me}

Substituent effects in the formation of a few acenaphthenone-2-ylidene ketones and their molecular docking studies and in silico ADME profile

We observed intriguing substituent effects in the reaction between 4-substituted acetophenones and acenaphthenequinone in the presence of KOH in methanol. In all cases, expected Claisen-Schimdt condensation was the first step. However, depending on the nature of 4-substituent on acetophenone, the initially formed condensation product remain unchanged or underwent Domino sequence of reactions to give three different 2:2 adducts arising through three distinct pathways. The interactions of acenaphthenone-2-ylidene ketones with the target proteins were performed by molecular docking studies. The prediction of in silico ADME belongings of the synthesized compounds revealed substantial drug-likeness characters based on Lipinski's rules.

Ground-State Electron Transfer as an Initiation Mechanism for Biocatalytic C-C Bond Forming Reactions

The development of non-natural reaction mechanisms is an attractive strategy for expanding the synthetic capabilities of substrate promiscuous enzymes. Here, we report an "ene"-reductase catalyzed asymmetric hydroalkylation of olefins using α-bromoketones as radical precursors. Radical initiation occurs via ground-state electron transfer from the flavin cofactor located within the enzyme active site, an underrepresented mechanism in flavin biocatalysis. Four rounds of site saturation mutagenesis were used to access a variant of the "ene"-reductase nicotinamide-dependent cyclohexanone reductase (NCR) from Zymomonas mobiles capable of catalyzing a cyclization to furnish β-chiral cyclopentanones with high levels of enantioselectivity. Additionally, wild-type NCR can catalyze intermolecular couplings with precise stereochemical control over the radical termination step. This report highlights the utility for ground-state electron transfers to enable non-natural biocatalytic C-C bond forming reactions.

Rh(iii)-catalyzed diastereoselective cascade annulation of enone-tethered cyclohexadienonesviaC(sp2)-H bond activation

Herein, we report highly diastereoselective arylative cyclization of enone-tethered cyclohexadienonesviaRh(iii)-catalyzed C-H activation ofN-methoxybenzamides. This reaction proceeds through the formation of a five-membered rhodacycle followed by bis-Michael cascade annulation to access functionalized bicyclic scaffolds with four contiguous stereocenters with a broad substrate scope. These products have excellent functional handles, allowing further synthetic transformation to increase the structural complexity. Furthermore, mechanistic studies of arylative cyclization and a gram-scale experiment are also presented.

Screening Hit to Clinical Candidate: Discovery of BMS-963272, a Potent, Selective MGAT2 Inhibitor for the Treatment of Metabolic Disorders

MGAT2 inhibition is a potential therapeutic approach for the treatment of metabolic disorders. High-throughput screening of the BMS internal compound collection identified the aryl dihydropyridinone compound 1 (hMGAT2 IC50 = 175 nM) as a hit. Compound 1 had moderate potency against human MGAT2, was inactive vs mouse MGAT2 and had poor microsomal metabolic stability. A novel chemistry route was developed to synthesize aryl dihydropyridinone analogs to explore structure-activity relationship around this hit, leading to the discovery of potent and selective MGAT2 inhibitors 21f, 21s, and 28e that are stable to liver microsomal metabolism. After triaging out 21f due to its inferior in vivo potency, pharmacokinetics, and structure-based liabilities and tetrazole 28e due to its inferior channel liability profile, 21s (BMS-963272) was selected as the clinical candidate following demonstration of on-target weight loss efficacy in the diet-induced obese mouse model and an acceptable safety and tolerability profile in multiple preclinical species.

Copper-Catalyzed N-O Cleavage of α,β-Unsaturated Ketoxime Acetates toward Structurally Diverse Pyridines

The copper-catalyzed [4 + 2] annulation of α,β-unsaturated ketoxime acetates with 1,3-dicarbonyl compounds for the synthesis of three classes of structurally diverse pyridines has been developed. This method employs 1,3-dicarbonyl compounds as C2 synthons and enables the synthesis of multifunctionalized pyridines with diverse electron-withdrawing groups in moderate to good yields. The mechanistic investigation suggests that the reactions proceed through an ionic pathway.

Catalyst-free green synthesis and study of antioxidant activity of new pyrazole derivatives

In this research, a novel procedure for the synthesis of pyrazole derivatives in excellent yields was studied using catalyst-free multicomponent reaction of isoquinoline, activated acetylenic compounds, alkyl bromides, triphenylphosphine and hydrazine in

Visible-light driven synthesis of polycyclic benzo[: D] [1,3]oxazocine from 2-aminochalcone

Herein, we report a tandem cycloisomerization/nucleophilic addition/cyclization of 2-amino chalcone with bifunctional nucleophiles driven by visible light. This cascade process is realized by the irradiation of a blue LED at room temperature, which provides a concise route to structurally diverse benzo[d][1,3]oxazocine scaffolds. Mechanistic studies show that the reaction is initiated with the E to Z isomerization of a C-C double bond upon the irradiation of visible light, followed by cyclization/rearomatization to generate a transient quinolinium intermediate, which is trapped by the nucleophile and cyclized to produce the polycyclic benzo[d][1,3]oxazocine.

Organocatalytic Enantioselective Selenosulfonylation of a C-C Double Bond to Form Two Stereogenic Centers in an Aqueous Medium

Organocatalytic selenosulfonylation of the C-C double bond of α,β-unsaturated ketones to construct two contiguous stereogenic centers in an aqueous medium was described. A series of α-selenyl and β-sulfonyl ketones with various functional groups were synthesized in good yields and enantioselectivities with saturated NaCl solution as the solvent. In addition, this protocol had been successfully scaled up to a decagram scale via a simple workup procedure.

A Ba/Pd Catalytic System Enables Dehydrative Cross-Coupling and Excellent E-Selective Wittig Reactions

A Ba/Pd cooperative catalysis system was developed to enable the dehydrative cross-coupling of allylic alcohols with P-ylides to occur directly and promote a subsequent Wittig reaction in one pot. A variety of multisubstituted 1,4-dienes were isolated in good to excellent yields with broad P-ylides (stabilized by both ester and ketone carbonyl groups) and aldehyde (aliphatic and aromatic) substrates with excellent E selectivity.