79314-55-9

Basic information

• Product Name: 1-Pentanone, 3-hydroxy-2-methyl-1-phenyl-
• CAS NO: 79314-55-9
• Molecular Formula: C12H16O2
• Molecular Weight: 192.258
• Mol File: 79314-55-9.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: 1-Pentanone, 3-hydroxy-2-methyl-1-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pentanone, 3-hydroxy-2-methyl-1-phenyl-(79314-55-9)
• EPA Substance Registry System: 1-Pentanone, 3-hydroxy-2-methyl-1-phenyl-(79314-55-9)

Safety Data

• Hazardous Substances Data: 79314-55-9(Hazardous Substances Data)

Upstream product

• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 123-38-6 propionaldehyde 
• 93-55-0 1-phenyl-propan-1-one 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 19347-08-1 acetic acid 1-methyl-2-oxo-2-phenyl-ethyl ester 
• 6084-15-7 2-iodo-1-phenylpropan-1-one 
• 57204-88-3 propiophenone lithium enolate 
• 73739-31-8 (3SR,2RS)-1-phenyl-2-methyl-3-hydroxy-pentan-1-one 
• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 71268-59-2 (E)-1-phenyl-1-(trimethylsiloxy)propene 

Downstream Products

• 73739-31-8 (3SR,2SR)-1-phenyl-2-methyl-3-hydroxy-pentan-1-one 
• 13618-19-4 1-phenyl-2-methyl-1,3-pentanedione 
• 93-55-0 1-phenyl-propan-1-one 
• 124306-44-1 (E)-2-methyl-1-phenyl-2-penten-1-one 

Relevant articles and documents

Borane-Catalyzed Direct Asymmetric Vinylogous Mannich Reactions of Acyclic α,β-Unsaturated Ketones

Herein, we report that, by using chiral bicyclic bisborane catalysts, we have achieved the first highly regio-, diastereo-, and enantioselective direct asymmetric vinylogous Mannich reactions of acyclic α,β-unsaturated ketones. The strong Lewis acidity and steric bulk of the bisborane catalysts were essential for the observed high yields and selectivities.

Neodymium(III)-mediated reformatsky-type reactions of α-halo ketones with carbonyl compounds

In a neodymium(III) iodide induced process, α-bromo ketones 1 and aldehydes 2 are effectively converted into aldol products 3. This Reformatsky-type reaction proceeds through the formation of a neodymium enolate at room temperature in CH2Cl2. The analogous reaction in the presence of NdBr3/NaI at 50°C in THF favors the formation of corresponding aldol-Tishchenko products 5 in good yields. Studies to define the scope and limitations of these reactions mediated by neodymium(III) salts are also described. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Diastereomer-differentiating photochemistry of β-arylbutyrophenones: Yang cyclization versus type II elimination

The diastereomers of ketones 2 and 3 are shown to exhibit distinct photochemical reactivities due to conformational preferences; while the anti isomers of 2 and 3 undergo efficient Yang cyclization in 75-90% yields with a remarkable diastereoselectivity (> 90%), the syn isomers predominantly undergo Norrish Type II elimination. The differences in the product profiles of the diastereomers are consistent with a mechanistic picture involving the formation of precursor diastereomeric triplet 1,4-biradicals in which the substituents at α and β-positions stabilize the cisoid (cyclization) or transoid (elimination) geometry. The fact that such a diastereomeric relationship does indeed ensue at the triplet-excited-state itself is demonstrated via the nanosecond laser-flash photolysis of model ketones 1. The diastereomeric discrimination in the product profiles observed for ketones 2 and 3 as well as in the triplet lifetimes observed for ketones 1 can both be mechanistically traced back to different conformational preferences of the ground-state diastereomeric ketones and the intermediary 1,4-biradicals. Additionally, it emerges from the present study that the syn and anti diastereomers of ketones 2 and 3 represent two extremes of a broad range of widely examined butyrophenones, which lead to varying degrees of Yang photocyclization depending on the alkyl substitution pattern.