1777-56-6

Usage

Uses

Used in Organic Synthesis:
1-(4-chlorophenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethanone is utilized as an intermediate in organic synthesis for the production of various complex organic molecules. Its unique reactivity, stemming from the presence of the chlorophenyl and triphenylphosphine groups, allows for the creation of a wide range of chemical products.
Used in Transition Metal Catalysis:
In the field of transition metal catalysis, 1-(4-chlorophenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethanone serves as an essential ligand. Its incorporation into catalytic systems enhances the efficiency and selectivity of various chemical reactions, making it a valuable component in the development of advanced catalytic processes.
Used in Pharmaceutical Industry:
1-(4-chlorophenyl)-2-(triphenyl-lambda~5~-phosphanylidene)ethanone is employed as a key building block in the synthesis of certain pharmaceutical compounds. Its unique structural features enable the development of novel drugs with potential applications in various therapeutic areas.
Used in Chemical Research:
This organophosphorus compound is also used in academic and industrial research settings to study its properties and explore its potential in the development of new materials, catalysts, and chemical processes. Its unique reactivity and structural features make it an interesting subject for further investigation and application in the field of chemistry.

Upstream product

• 99-91-2 para-chloroacetophenone 
• 603-35-0 triphenylphosphine 
• 536-38-9 4-chlorobenzoylmethyl bromide 
• 825-40-1 2-bromo-p-chloroacetophenone 
• 59956-67-1 4-chlorobenzyl 2-bromoacetate 

Downstream Products

• 89781-40-8 C₁₂H₁₁ClO₃ 
• 4953-95-1 N-(2-methylphenyl)cyanothioformanilide 
• 6616-22-4 [2-(4-Chloro-phenyl)-1-methyl-2-oxo-ethyl]-triphenyl-phosphonium; iodide 
• 23336-93-8 (Z)-3-(2-(4-chlorophenyl)-2-oxoethylidene)indolin-2-one 
• 183947-04-8 (E)-3-(2-(4-chlorophenyl)-2-oxoethylidene)indolin-2-one 
• 198974-12-8 2-[2-(4-chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one 
• 791-28-6 Triphenylphosphine oxide 
• 5604-31-9 5-(4-chlorophenyl)-1H-1,2,3-triazole 
• 288072-76-4 5-(4-Chloro-phenyl)-2-[2-(4-chloro-phenyl)-2-oxo-eth-(E)-ylidene]-furan-3-one 
• 2689-81-8 (4-chlorophenacyl)triphenylphosphonium bromide 
• 67864-02-2 4′-chloro-1-phenylbut-2-en-1-one 
• 207731-62-2 (E)-1-(4-Chloro-phenyl)-3-cyclohexyl-propenone 

Relevant academic research and scientific papers

Synthesis and characterisation of Hg (II) and Ag (I) complexes of 4-fluorobenzoylmethylenetriphenylphosphorane and 4-chlorobenzoyl methylenetriphenylphosphorane, with spectroscopic studies

4-flourobenzyloxymethylenetriphenylphosphorane ylide [Ph 3PCHCOC6H4F], (FBPPY), and 4- chlorobenzyloxymethylenetriphenylphosphorane ylide [Ph3PCHCOC 6H4Cl](CBPPY), have been synthesised. Th

One-pot synthesis of new hydantoin (thiohydantoin) derivatives and evaluation of their antibacterial and antioxidant activities

One-pot four-component reactions of phenacyl bromides, parabanic or thioparabanic acids, thiophenols, and triphenylphosphine in the presence of triethylamine afforded new derivatives of hydantoin or thiohydantoin in good to high yields (65%-90%). Their an

Selective Construction of C?C and C=C Bonds by Manganese Catalyzed Coupling of Alcohols with Phosphorus Ylides

Herein, we report the manganese catalyzed coupling of alcohols with phosphorus ylides. The selectivity in the coupling of primary alcohols with phosphorus ylides to form carbon-carbon single (C?C) and carbon-carbon double (C=C) bonds can be controlled by the ligands. In the conversion of more challenging secondary alcohols with phosphorus ylides the selectivity towards the formation of C?C vs. C=C bonds can be controlled by the reaction conditions, namely the amount of base. The scope and limitations of the coupling reactions were thoroughly evaluated by the conversion of 21 alcohols and 15 ylides. Notably, compared to existing methods, which are based on precious metal complexes as catalysts, the present catalytic system is based on earth abundant manganese catalysts. The reaction can also be performed in a sequential one-pot reaction generating the phosphorus ylide in situ followed manganese catalyzed C?C and C=C bond formation. Mechanistic studies suggest that the C?C bond was generated via a borrowing hydrogen pathway and the C=C bond formation followed an acceptorless dehydrogenative coupling pathway. (Figure presented.).

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.

Catalytic Synthesis of 1 H-2-Benzoxocins: Cobalt(III)-Carbene Radical Approach to 8-Membered Heterocyclic Enol Ethers

The metallo-radical activation of ortho-allylcarbonyl-aryl N-arylsulfonylhydrazones with the paramagnetic cobalt(II) porphyrin catalyst [CoII(TPP)] (TPP = tetraphenylporphyrin) provides an efficient and powerful method for the synthesis of novel 8-membered heterocyclic enol ethers. The synthetic protocol is versatile and practical and enables the synthesis of a wide range of unique 1H-2-benzoxocins in high yields. The catalytic cyclization reactions proceed with excellent chemoselectivities, have a high functional group tolerance, and provide several opportunities for the synthesis of new bioactive compounds. The reactions are shown to proceed via cobalt(III)-carbene radical intermediates, which are involved in intramolecular hydrogen transfer (HAT) from the allylic position to the carbene radical, followed by a near-barrierless radical rebound step in the coordination sphere of cobalt. The proposed mechanism is supported by experimental observations, density functional theory (DFT) calculations, and spin trapping experiments.

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.

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.

C(sp2)-H Bond Multiple Functionalization in Air for Construction of Tetrahydrocarbazoles with Continuous Quaternary Carbons and Polycyclic Diversification

The C(sp2)-H function of indole ketone with diazo compound via a rhodium(II)-catalyzed intramolecular electrophilic trapping reaction under mild conditions in air was demonstrated. The established methodology provided a highly efficient approach for direct synthesis of mutisubstituted tetrahydrocarbazoles with continuous quaternary carbons. The resulting products facilitate further modification to conveniently construct tetrahydrocarbazoles with additional fused heterocyclic rings. By phenotypic screening, several products exhibit good anticancer bioctivities in osteosarcoma cell lines.

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.