1450-07-3

Usage

General Description

1-Propanone, 1-phenyl-2-(triphenylphosphoranylidene)-, also known as benzylideneacetone or α-phenyl-α-(triphenylphosphoranylidene)propanone, is a chemical compound with the formula C19H18O. It is a yellow crystalline solid that is commonly used as a reagent in organic synthesis, particularly in the formation of chalcone derivatives. 1-Propanone, 1-phenyl-2-(triphenylphosphoranylidene)- is known for its ability to act as a Michael acceptor, making it useful for the synthesis of various organic compounds. It is also used as a ligand in coordination chemistry, forming stable complexes with metal ions. Its unique structure and reactivity make it a valuable tool in the field of organic and inorganic chemistry.

Upstream product

• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 603-35-0 triphenylphosphine 
• 98-88-4 benzoyl chloride 
• 1754-88-7 ethylenetriphenylphosphorane 
• 896-33-3 ethyltriphenylphosphonium chloride 
• 3740-01-0 <1-Trimethylsilyl-ethyl>-triphenyl-phosphoniumiodid 
• 1530-32-1 ethyltriphenylphosphonium bromide 
• 93-55-0 1-phenyl-propan-1-one 
• 2689-63-6 1-benzoylethylidenephosphonium bromide 
• 82294-33-5 1-trimethylsilyl ethylene triphenylphosphorane 
• 93-97-0 benzoic acid anhydride 
• 1484-17-9 S-ethyl thiobenzoate 

Downstream Products

• 21555-06-6 2-Methyl-1-phenyl-3-phenylimino-propenone 
• 84370-15-0 Trifluoro-methanesulfonate((Z)-1-methyl-2-phenyl-2-trifluoromethanesulfonyloxy-vinyl)-triphenyl-phosphonium; 
• 25559-56-2 2-methyl-3-oxo-N-phenyl-3-phenylpropanamide 
• 102-07-8 bis(diphenyl)urea 
• 55324-06-6 4-methyl-5-phenyl-1H-1,2,3-triazole 
• 791-28-6 Triphenylphosphine oxide 
• 557085-44-6 (E)-4-hydroxy-2-methyl-1-phenyl-2-buten-1-one 
• 99598-38-6 N,2-Dibenzoylpropionamid 
• 1329669-94-4 (E)-2-(2-methyl-3-oxo-3-phenylprop-1-en-1-yl)benzaldehyde 
• 65495-77-4 3-(methyl)-4-oxo-4-phenylbutanal 
• 1139768-51-6 2-methyl-1,4-diphenyl-3-buta-2,3-dien-1-one 
• 30515-35-6 2-methyl-1-phenylbuta-2,3-dien-1-one 
• 769-60-8 2-methyl-1-phenylprop-2-en-1-one 
• 84370-15-0 Trifluoro-methanesulfonate((Z)-1-methyl-2-phenyl-2-trifluoromethanesulfonyloxy-vinyl)-triphenyl-phosphonium; 

Relevant academic research and scientific papers

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.

Transition-Metal-Free Reductive Deoxygenative Olefination with CO2

A new transition-metal-free reductive deoxygenative olefination of phosphorus ylides with CO2, an abundant and sustainable C1 chemical feedstock, is described. This catalytic CO2 fixation afforded β-unsubstituted acrylates and vinyl ketones in good yields with broad scope and good functional group tolerance under mild reaction conditions. Cost-effective and easily handled polymethylhydrosiloxane was used as a reductant. Bis(silyl)acetal was proved to be the key intermediate in this reductive functionalization of CO2.

Organocatalytic Redox Isomerization of Electron-Deficient Allylic Alcohols: Synthesis of 1,4-Ketoaldehydes

An organocatalytic redox isomerization strategy has been developed for the synthesis of 1,4-ketoaldehydes. DABCO was found to be the best catalyst for the isomerization of -hydroxy enones. With 20 mol % of DABCO as catalyst and DMSO as the solvent high yi

Synthesis of C-glycosyl isoxazoles and branched-chain enuloses from 2,3-O-isopropylidene-D-glyceraldehyde

The synthesis of 5-glycosyl isoxazoles with 3-alkyl-, 3-aryl, 3,4-dialkyl, 3-aryl-4-alkyl or 3-alkyl-4-bromo substituents is reported. Deoxyenuloses were obtained from reaction of 2,3-O-isopropylidene-D-glyceraldehyde and several phosphorus ylides, which contain a carbonyl group, by a Wittig reaction. C-glycosyl α,β-unsaturated ketones were obtained, with the polyhydroxylate chain lengthened by two or three carbon atoms. In the second phase the ketones were transformed into the corresponding C-glycosyl α,β-unsaturated ketoximes, leading to the C-glycosyl isoxazoles, which were converted into the title compounds via removal of the isopropylidene group of suitably protected carbohydrates. The solubility of the synthetized C-glycosyl isoxazoles were modified by free hydroxyl groups in such a way that their behaviour against certain viruses and their potential antiviral activity could be studied.

CONVENIENT PREPARATION OF UNSYMMETRICALLY SUBSTITUTED BENZILS BY PERMANGANATE OXIDATION OF β-OXO PHOSPHORUS YLIDES

Oxidative cleavage of a range of ylides 4 with R1 and/or R2 being aromatic groups, using KMnO4 in a two-phase system, affords unsymmetrical benzils and 1-arylpropane-1,2-diones 5 in moderate to good yield, and the ylide formation and oxidation can be combined in a convenient one-pot method.Key words: Phosphorus ylides, oxidation, 1,2-diketones, benzils, permanganate, oxoalkylidenetriphenylphosphoranes.

Synthesis and reactions of [1-(trialkylsilyl)alkylidene]triphenylphosphoranes

Alkylidenetriphenylphosphoranes 1 react with trialkyl halosilanes 2 to afford silylated alkylidenephosphoranes 5, which can be converted to acylated alkylidenephosphoranes 8 and 10 by trimethylsilyl carboxylates 6 or carboxylic anhydrides 10. Bis(acylalkylidenephosphoranes) 13-15 are available from 5 and bis(trimethylsilyl) dicarboxylates 12 or cyclic or polymeric anhydrides 16, 17.

Reactions with Phosphine Alkylenes, XLII. A Sequence for the Preparation of Acetylenes Starting from Carboxylic Chlorides and Phosphorus Ylides via 1,2-Diketones.

Phosphorus ylides 1 and carboxylic chlorides 2 react with transylidation to give acyl ylides 3 which are oxidized with the adduct of ozone to triphenyl phosphite to yield 1,2-diketones 5.These are converted into the bis(hydrazones) 6 which are oxidized with O2/CuCl in pyridine giving acetylenes 7.