63072-14-0

Basic information

• Product Name: Ethanone, 1-(4-fluorophenyl)-2-(triphenylphosphoranylidene)-
• CAS NO: 63072-14-0
• Molecular Formula: C26H20FOP
• Molecular Weight: 398.416
• Mol File: 63072-14-0.mol

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-(4-fluorophenyl)-2-(triphenylphosphoranylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(4-fluorophenyl)-2-(triphenylphosphoranylidene)-(63072-14-0)
• EPA Substance Registry System: Ethanone, 1-(4-fluorophenyl)-2-(triphenylphosphoranylidene)-(63072-14-0)

Safety Data

• Hazardous Substances Data: 63072-14-0(Hazardous Substances Data)

Upstream product

• 603-35-0 triphenylphosphine 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 120302-61-6 Br^(1-)*C₂₆H₂₁FOP⁽¹⁺⁾ 
• 1006-39-9 1-(2-bromo-4-fluorophenyl)ethanone 

Downstream Products

• 28081-14-3 1-(4-fluorophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one 
• 791-28-6 Triphenylphosphine oxide 
• 1189060-08-9 ethyl (E,E)-6-(4-fluorophenyl)-6-oxohexa-2,4-dienoate 
• 1256284-90-8 1-(4-fluorophenyl)-2-(9-methyl-2,3,4,9-tetrahydro-1H-carbazol-4-yl)ethanone 
• 1647059-08-2 C₁₇H₂₃FN₂O₂Si 
• 1623752-22-6 5-((tert-butyldimethylsilyl)oxy)-1-(4-fluorophenyl)pent-2-en-1-one 
• 1616777-24-2 (E)-4-diazo-5-(4-fluorophenyl)-5-oxopent-2-enal 
• 1647059-14-0 C₁₁H₉FN₂O₂ 
• 1623751-96-1 (1-benzyl-1H-indol-7-yl)(4-fluorophenyl)methanone 
• 405275-40-3 (4-fluorophenyl)(1H-indol-7-yl)methanone 
• 1542159-01-2 C₂₄H₁₆F₂O₂ 
• 1542158-85-9 2-(2-(4-fluorobenzoyl)-3-(nitromethyl)-2,3-dihydro-1H-inden-1-yl)-1-(4-fluorophenyl)ethan-1-one 
• 1435944-22-1 tert-butyl 2-(4-fluorobenzoyl)indoline-1-carboxylate 
• 1435944-11-8 tert-butyl (2-(3-(4-fluorophenyl)-3-oxopropyl)phenyl)carbamate 

Relevant articles and documents

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.

Tuneable access to indole, indolone, and cinnoline derivatives from a common 1,4-diketone Michael acceptor

A convergent strategy is reported for the construction of nitrogen-containing heterocycles from common substrates: 1,4-diketones and primary amines. Indeed, by just varying the substrates, the substituents, or the heating mode, it is possible to selectively synthesize indole, indolone (1,5,6,7-tetrahydroindol-4-one), or cinnoline (5,6,7,8-tetrahydrocinnoline) derivatives in moderate to excellent yields.

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.

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.

Tandem Wittig Reaction-Ring Contraction of Cyclobutanes: A Route to Functionalized Cyclopropanecarbaldehydes

An original tandem reaction consisting of a Wittig reaction-ring contraction process between α-hydroxycyclobutanone and phosphonium ylides has been developed. Highly functionalized cyclopropanecarbaldehydes are obtained in good to high yield.

PYRROLIDINE DERIVATIVES AS PPAR AGONISTS

The present invention discloses a class of pyrrolidine derivatives as PPAR agonist, and their use for the treatment of some diseases of PPAR receptor-associated pathways (such as nonalcoholic steatohepatitis and concurrent fibrosis, insulin resistance, primary biliary cholgangitis, dyslipidenmia, hyperlipidemia, hypercholesterolemia, atherosclerosis, hypertriglyceridemia, cardiovascular disease, obesity or the like). In particular, the present invention discloses a compound represented by Formula (I) or a pharmaceutically acceptable salt thereof.

Fe-Catalyzed Cycloisomerization of Aryl Allenyl Ketones: Access to 3-Arylidene-indan-1-ones

A cycloisomerization of aryl allenyl ketones to 3-arylidene-indan-1-ones using a cationic Fe-complex as a catalyst is reported. The catalyst opens a synthetically interesting reaction pathway to this surprisingly underrepresented class of indanones that are not accessible using alternative catalytic systems.

Nonenzymatic Dynamic Kinetic Resolution of in situ Generated Hemithioacetals: Access to 1,3-Disubstituted Phthalans

The first nonenzymatic DKR reaction of hemithioacetals is developed. Hemithioacetals were formed in situ via thiol addition and subsequently underwent an intramolecular oxa-Michael reaction. The scope of the reaction was quite broad ranging from aliphatic to aromatic substituents and 1,3-disubstituted-1,3-dihyroisobenzofuran products were obtained in good yields with moderate diastereoselectivities and high enantioselectivities. (Figure presented.).

Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents

Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.