1777-59-9

Usage

Uses

Used in Organic Synthesis:
Ethanone, 1-(2-naphthalenyl)-2-(triphenylphosphoranylidene)is utilized as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its unique structure allows it to participate in reactions that are otherwise challenging to achieve with simpler compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, Ethanone, 1-(2-naphthalenyl)-2-(triphenylphosphoranylidene)is used as a building block for the development of novel pharmaceuticals. Its ability to form strong carbon-nitrogen bonds makes it a promising candidate for the synthesis of new drug molecules with enhanced properties.
Used in Chemical Catalysts:
Ethanone, 1-(2-naphthalenyl)-2-(triphenylphosphoranylidene)is also employed as a component in the design of chemical catalysts. Its involvement in catalytic processes can improve the efficiency and selectivity of chemical reactions, which is crucial for the advancement of green chemistry and sustainable industrial processes.
Further research and investigation are essential to uncover the full spectrum of applications and properties of Ethanone, 1-(2-naphthalenyl)-2-(triphenylphosphoranylidene)-, ensuring its potential is fully realized across different industries.

Upstream product

• 2689-60-3 (2-Naphthoyl)methyltriphenylphosphonium bromide 
• 603-35-0 triphenylphosphine 
• 613-54-7 2-Bromo-2'-acetonaphthone 
• 93-08-3 methyl 2-naphthyl ketone 

Downstream Products

• 57221-66-6 (E)-1-Naphthalen-2-yl-3-(2-nitro-phenyl)-propenone 
• 93-09-4 naphthalene-2-carboxylate 
• 176100-46-2 1-(naphthalen-2-yl)-4-phenylbutane-1,4-dione 
• 1451011-95-2 C₁₉H₁₅NO 

Relevant academic research and scientific papers

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.

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.

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.

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.

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.).

Synthesis of trifluoromethyl-/cyclopropyl-substituted 2-isoxazolines by DBU-promoted domino reaction

NTrifluoromethyl and cyclopropyl substituted 2-isoxazolines were synthesized via a DBU-promoted domino reaction of β-trifluoromethyl-/β-cyclopropyl-substituted enones with hydroxylamine. The domino reaction consists of a Michael addition and the followed cyclization. A wide range of 3-substituted 5-cyclopropyl-5- trifluoromethyl-2-isoxazolines were obtained in good to excellent yields under mild reaction conditions. The method could also apply to other trifluoromethyl-substituted enones.

Isothiourea-mediated one-pot synthesis of functionalized pyridines

Acids to bases: The synthesis of 2,4,6-trisubstituted pyridines from (phenylthio)acetic acid and a range of α,β-unsaturated ketimines is reported. This process proceeds by intermolecular Michael addition/ lactamization, thiophenol elimination, and N- to O

Crossed intramolecular rauhut-currier-type reactions via dienamine activation

The intramolecular Rauhut-Currier reaction creates a carbon-carbon bond between two tethered Michael acceptors. Previous asymmetric versions have relied on 1,4-additions of chiral nucleophilic catalysts. Herein, we Investigate a novel strategy that involves the formation of electron rich dienamines as key Intermediates. Our methodology provides an efficient entry to the iridoid framework.

New access to trisubstitutea 3-pyrrolines under phosphine catalysis

Conjugated dienes, properly activated by electron-withdrawing groups on both ends, are shown to be suitable substrates for phosphinepromoted organocatalytic processes. Their reactions with imines, under phosphine catalysis, afford a new and efficient synthetic approach to functionalized 3-pyrrolines.

Synthesis and characterization of transition metal (Hg(II), Ag(I) and Cd(II)) complexes of some new: Phosphorus ylides

Reaction of two new phosphorus ylides Ph3PCHCOC 10H7 (Y1) and Ph3PCHCOC 4H3S(Y2) with mercury(II) halides and a previously reported ylide (P-tolyl)3PCHCOOCH