111114-35-3

Basic information

• Product Name: 3-Pentanone, 2-(triphenylphosphoranylidene)-
• CAS NO: 111114-35-3
• Molecular Formula: C23H23OP
• Molecular Weight: 346.409
• Mol File: 111114-35-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 3-Pentanone, 2-(triphenylphosphoranylidene)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pentanone, 2-(triphenylphosphoranylidene)-(111114-35-3)
• EPA Substance Registry System: 3-Pentanone, 2-(triphenylphosphoranylidene)-(111114-35-3)

Safety Data

• Hazardous Substances Data: 111114-35-3(Hazardous Substances Data)

Upstream product

• 1754-88-7 ethylenetriphenylphosphorane 
• 3740-01-0 <1-Trimethylsilyl-ethyl>-triphenyl-phosphoniumiodid 
• 603-35-0 triphenylphosphine 
• 96-22-0 pentan-3-one 
• 815-52-1 2-bromopentan-3-one 
• 123-62-6 propionic acid anhydride 
• 82294-33-5 1-trimethylsilyl ethylene triphenylphosphorane 
• 111114-34-2 triphenyl(1-propionylethyl)phosphonium bromide 
• 16844-98-7 trimethylsilyl propionate 
• 51314-22-8 C₂₁H₁₉O₂P 

Downstream Products

• 129083-11-0 1-Hydroxy-2-methyl-4-(triphenyl-λ⁵-phosphanylidene)-pentan-3-one 
• 72522-40-8 (4RS,6SR,7SR)-Serricornin 
• 72598-35-7 (-)-serricornin 
• 72522-40-8 (4R,6S,7S)-7-hydroxy-4,6-dimethyl-3-nonanone 
• 350246-40-1 (7S,8R,8aS,6E)-7,8-Dihydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizidine 
• 350246-39-8 (8R,8aS,6E)-8-Hydroxy-8-methyl-[(2R,4E,6S)-2,5-dimethyl-6-benzyloxymethyloxy-4-octenylidene]octahydroindolizin-7-done 
• 350246-38-7 (8R,8aS)-6-((E)-(2R,6S)-6-Benzyloxymethoxy-1-hydroxy-2,5-dimethyl-oct-4-enyl)-8-hydroxy-8-methyl-hexahydro-indolizin-7-one 
• 350246-36-5 (2R,6S,4E)-6-Benzyloxymethyloxy-1-(tert-butyldiphenylsiloxy)-2,5-dimethyl-4-octene 
• 350246-35-4 (2R,6S,4E)-1-(tert-Butyldiphenylsiloxy)-2,5-dimethyl-4-octen-6-ol 
• 350246-37-6 (2R,6S,4E)-6-Benzyloxymethyloxy-2,5-dimethyl-4-octen-1-ol 
• 350246-24-1 (2R,6S,4E)-6-Benzyloxymethyloxy-2,5-dimethyl-4-octen-1-al 
• 350246-34-3 (2R,4E)-1-(tert-Butyldiphenylsiloxy)-2,5-dimethyl-4-octen-6-one 

Relevant articles and documents

The synthesis of (+)-Allopumiliotoxin 323B′

This paper describes the synthesis of (+)-allopumiliotoxin 323B′ (1) using the intramolecular [3 + 2]-cyclo-addition reaction of the (Z)-N-alkenylnitrone 4. This synthesis began with (R)-tert-butyl-3-hydroxy-pent-4-enoate [(R)-13] which was obtained by enzymatic resolution with Amano PS lipase. A series of manipulations gave intermediate 17 and in situ coupling with 4-benzoyloxybutanal lead to the (Z)-N-alkenylnitrone 4 which underwent an intramolecular [3 + 2]-cycloaddition reaction to give the isoxazolidine 3 as the major cycloadduct. Isoxazolidine 3 provided the piperidinone 24 which upon diastereofacial selective addition of MeMgBr gave the required tertiary alcohol 25. Formation of the indolizidine core 2 was achieved by an intramolecular SN2 reaction. The side chain was assembled from a Wittig reaction between the phosphorane 8 and the enantiomerically pure aldehyde 9. Further modifications afforded the aldehyde 7 which underwent an aldol condensation with the potassium enolate of the indolizidone core 2. Dehydration gave the enone 37 which was converted into the anti-diol 38 by intramolecular hydride reduction. Finally, deprotection of the BOM protecting group gave (+)-allopumiliotoxin 323B′ (1).

Facile synthesis of (-)-serricornin by means of palladium-catalyzed hydrogenolysis of alkenyloxiranes

Chiral synthesis of (-)-serricornin by using palladium-catalyzed stereoselective hydrogenolysis of the alkenyloxirane to the homoallylic alcohol with formic acid as a key step was carried out.

Pheromones, 65. - Identification of the Volatile Components of the Mandibular Gland Secretion of the Ant Manica rubida: Structure Elucidation, Synthesis, and Absolute Configuration of Manicone

By means of gas chromatography and mass spectrometry, manicone, (4E)-4,6-dimethyl-4-octen-3-one (1), was identified as the main component of the mandibular gland secretion of the ant Manica rubida.In addition the presence of homomanicone (2), bishomomanicone (3), normanicone (7), and a few aliphatic aldehydes and ketones was also evident in the gland.Racemic 1, 2, and 7 and optically active dihydromanicone (4), were synthesized.The (S) configuration of 1 was determined by complexation gas chromatography, on a chiral phase, of 4 as well as of the hydrogenation products of racemic and natural 1.