17180-49-3

Basic information

• Product Name: 4-Penten-1-one, 2-methyl-1-phenyl-
• CAS NO: 17180-49-3
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Mol File: 17180-49-3.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: 4-Penten-1-one, 2-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Penten-1-one, 2-methyl-1-phenyl-(17180-49-3)
• EPA Substance Registry System: 4-Penten-1-one, 2-methyl-1-phenyl-(17180-49-3)

Safety Data

• Hazardous Substances Data: 17180-49-3(Hazardous Substances Data)

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 71-43-2 benzene 
• 2004-70-8 1-methylbuta-1,3-diene 
• 100-52-7 benzaldehyde 
• 557-40-4 Allyl ether 
• 107-18-6 allyl alcohol 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 762-72-1 allyl-trimethyl-silane 
• 1356393-67-3 (E)-(3-(allyloxy)-3-phenylprop-1-en-1-yl)dimethyl(phenyl)silane 
• 82215-67-6 1-Phenyl-1-(tri-n-butylstannyloxy)-propen 
• 106-95-6 allyl bromide 
• 146431-09-6 N,N-dimethylhydrazone de methyl-2 phenyl-1 pentene-4 one 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 133464-91-2 2-(tert-Butyl-dimethyl-silanyloxy)-1-phenyl-propan-1-one 

Downstream Products

• 78167-61-0 (2-methylpent-4-en-1-yl)benzene 
• 65912-65-4 3-Methyl-2-phenyl-1,5-hexadien 
• 120536-73-4 (E)-2-methyl-1-phenylpent-3-en-1-one 
• 124306-44-1 (E)-2-methyl-1-phenyl-2-penten-1-one 
• 31366-05-9 (±)2-methyl-1-phenylpentan-1-one 
• 1616560-16-7 (E)-1-(2-methyl-1-phenylpent-4-en-1-ylidene)-2-phenylhydrazine 
• 94922-24-4 (3aS,6S,8aR)-6-Benzoyl-6-methyl-2-phenyl-4,5,6,7,8,8a-hexahydro-3aH-cyclopenta[f]isoindole-1,3-dione 
• 94922-14-2 1-benzoyl-1-methyl-5-methylenecyclohex-3-ene 
• 94922-13-1 1-benzoyl-1-methyl-3,4-bis(methylene)cyclopentane 
• 224426-62-4 1-phenyl-2-methyl-4,5-epoxypentan-1-one 
• 94922-10-8 2-bromo-4-benzoyl-4-methylhepta-1,6-diene 
• 145295-78-9 1-phenyl-2-methyl-2-(2-propen-1-yl)- 4-penten-1-one 

Relevant articles and documents

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α- And β-Functionalized Ketones from 1,3-Dienes and Aldehydes: Control of Regio- And Enantioselectivity in Hydroacylation of 1,3-Dienes

Ketones are among the most widely used intermediates in organic synthesis, and their synthesis from inexpensive feedstocks could be quite impactful. Regio- and enantioselective hydroacylation reactions of dienes provide facile entry into useful ketone-bearing chiral motifs with an additional latent functionality (alkene) suitable for further elaboration. Three classes of dienes, 2- or 4-monosubstituted and 2,4-disubstituted 1,3-dienes, undergo cobalt(I)-catalyzed regio- and enantioselective hydroacylation, giving products with high enantiomeric ratios (er). These reactions are highly dependent on the ligands, and we have identified the most useful ligands and reaction conditions for each class of dienes. 2-Substituted and 2,4-disubstituted dienes predominantly undergo 1,2-addition, whereas 4-substituted terminal dienes give highly enantioselective 4,1- or 4,3-hydroacylation depending on the aldehyde, aliphatic aldehydes giving 4,1-addition and aromatic aldehydes giving 4,3-addition. Included among the substrates are feedstock dienes, isoprene (US$1.4/kg) and myrcene (US$129/kg), and several common aldehydes. We propose an oxidative dimerization mechanism that involves a Co(I)/Co(III) redox cycle that appears to be initiated by a cationic Co(I) intermediate. Studies of reactions using isolated neutral and cationic Co(I) complexes confirm the critical role of the cationic intermediates in these reactions. Enantioselective 1,2-hydroacylation of 2-trimethylsiloxy-1,3-diene reveals a hitherto undisclosed route to chiral siloxy-protected aldols. Finally, facile syntheses of the anti-inflammatory drug (S)-Flobufen (2 steps, 92% yield, >99:1 er) and the food additive (S)-Dihydrotagetone (1 step, 83% yield; 96:4 er) from isoprene illustrate the power of this method for the preparation of commercially relevant compounds.

Enolonium Species—Umpoled Enolates

Enolonium species/iodo(III)enolates of carbonyl compounds have been suggested to be intermediates in a wide variety of hypervalent iodine induced chemical transformations of ketones, including α-C?O, α-C?N, α-C?C, and α-carbon–halide bond formation, but they have never been characterized. We report that these elusive umpoled enolates may be made as discrete species that are stable for several minutes at ?78 °C, and report the first spectroscopic identification of such species. It is shown that enolonium species are direct intermediates in C?O, C?N, C?Cl, and C?C bond forming reactions. Our results open up chemical space for designing a variety of new transformations. We showcase the ability of enolonium species to react with prenyl, crotyl, cinnamyl, and allyl silanes with absolute regioselectivity in up to 92 % yield.

Copper-catalyzed cyclization and azidation of γ,δ-unsaturated ketone O-benzoyl oximes

An intramolecular imination/azidation sequence has been realized through the tetrakis(acetonitrile)copper(I) hexafluorophophate [Cu(CH3CN)4PF6]-catalyzed reaction of γ,δ-unsaturated ketone O-benzoyl oximes with trimethylsi