23406-52-2

Basic information

• Product Name: (S)-3-Phenyl-2-butanone
• Synonyms: (3S)-3-Phenyl-2-butanone;(S)-3-Phenyl-2-butanone;[S,(+)]-3-Phenyl-2-butanone;Methyl[(S)-α-methylbenzyl] ketone
• CAS NO: 23406-52-2
• Molecular Formula: C₁₀H₁₂O
• Molecular Weight: 148.2
• Mol File: 23406-52-2.mol

Chemical Properties

• Boiling Point: 207.3±9.0 °C(Predicted)
• Appearance: /
• Density: 0.967±0.06 g/cm3(Predicted)
• CAS DataBase Reference: (S)-3-Phenyl-2-butanone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-Phenyl-2-butanone(23406-52-2)
• EPA Substance Registry System: (S)-3-Phenyl-2-butanone(23406-52-2)

Safety Data

• Hazardous Substances Data: 23406-52-2(Hazardous Substances Data)

Upstream product

• 7782-24-3 (S)-2-Phenylpropionic acid 
• 32123-84-5 3-phenylbut-3-en-2-one 
• 769-59-5 3-phenyl-butan-2-one 
• 512176-79-3 benzyl 3-oxo-2-phenylbutanoate 
• 103-79-7 1-phenyl-acetone 
• 1429767-28-1 4,4,5,5-tetramethyl-2-(3-phenylbut-1-en-2-yl)-1,3,2-dioxaborolane 
• 102-16-9 benzyl 2-phenylacetate 
• 103-82-2 phenylacetic acid 
• 512176-91-9 benzyl 2-acetyl-2-phenylpropanoate 
• 87841-67-6 C₂₀H₂₄O 
• 100-44-7 benzyl chloride 

Downstream Products

• 119788-61-3 (2R,3S)-2-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-1,3-diphenyl-butan-1-one 
• 119788-60-2 (2R*,3S*)-2-(tert-Butyldimethylsilyloxy)-2-methyl-1,3-diphenyl-1-butanon 
• 119788-55-5 (2R,3S)-2-Methyl-1,3-diphenyl-2-trimethylsilanyloxy-butan-1-one 
• 119788-54-4 (2R*,3S*)-2-Methyl-1,3-diphenyl-2-(trimethylsilyloxy)-1-butanon 
• 119788-74-8 (2S*,3S*)-2-Hydroxy-2-methyl-1,3-diphenyl-1-butanon 
• 119788-73-7 (2R*,3S*)-2-Hydroxy-2-methyl-1,3-diphenyl-1-butanon 
• 23406-53-3 ((R)-1,2-Dimethyl-allyl)-benzene 
• 33484-95-6 2-Phenyl-3-methyl-3-pentanol 
• 33484-95-6 2-Phenyl-3-methyl-3-pentanol 
• 26306-08-1 (S)-2-phenyl-butanone-⁽³⁾-oxime 

Relevant articles and documents

Catalytic enantioselective protoboration of disubstituted allenes. Access to alkenylboron compounds in high enantiomeric purity

Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0-5.0 mol % of chiral NHC-Cu complexes, B2(pin)2, and t-BuOH proceed to afford alkenyl-B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. T

BVMO-catalysed dynamic kinetic resolution of racemic benzyl ketones in the presence of anion exchange resins

4-Hydroxyacetophenone monooxygenase from Pseudomonas fluorescens ACB was employed in the presence of a weak anion exchange resin to perform dynamic kinetic resolutions of racemic benzyl ketones with high conversions and good optical purities. Different parameters that affect to the efficiency of the enzymatic Baeyer-Villiger oxidation and racemisation were analyzed in order to optimize the activity and selectivity of the biocatalytic system. The Royal Society of Chemistry.

Baeyer-Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters

The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic α-alkyl benzylketones with longer alkyl chains as well as with two substituted α-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis.

Selective Baeyer-Villiger oxidation of racemic ketones in aqueous-organic media catalyzed by phenylacetone monooxygenase

The enantioselective kinetic resolution of a set of racemic substituted 3-phenylbutan-2-ones employing phenylacetone monooxygenase (PAMO) in non-conventional media was performed. The studies have revealed the effects of a range of solvents on the biocatalytic properties of the biocatalyst. Also, the enzymatic oxidation of α-acetylphenylacetonitrile was performed using organic cosolvents. This has resulted in a dynamic kinetic resolution of this cyanoketone yielding enantiopure (R)-2-acetoxyphenylacetonitrile with moderate yields depending on the reaction conditions employed.

Enzymatic kinetic resolution of racemic ketones catalyzed by Baeyer-Villiger monooxygenases

A set of racemic cyclic and linear ketones, as well as 2-phenylpropionaldehyde, were tested as substrates in the enzymatic Baeyer-Villiger oxidation catalyzed by two Baeyer-Villiger monooxygenases: phenylacetone monooxygenase (PAMO) and 4-hydroxyacetophenone monooxygenase (HAPMO). Excellent enantioselectivites (E > 200) can be obtained in the kinetic resolution processes depending on the substrate structure and the reaction conditions. The parameters affecting the biocatalytic properties of these enzymes were also studied, in order to establish a deeper understanding of these novel biocatalysts.

Enantioselective kinetic resolution of 3-phenyl-2-ketones using Baeyer-Villiger monooxygenases

The enantioselective kinetic resolution of two 3-phenyl-2-ketones using four different Baeyer-Villiger monooxygenases (BVMO) expressed recombinantly in Escherichia coli was studied. The highest enantioselectivity (E = 82) was achieved for 3-phenyl-2-butanone using a BVMO originating from Pseudomonas fluorescens. A BVMO from Pseudomonas putida showed an opposite (R)-enantiopreference and E = 12.

Catalysed asymmetric protonation of simple linear keto-enolic species a route to chiral α-arylpropionic acids

The reaction cascade consisting of deprotection/decarboxylation/asymmetric protonation of enolic species, starting from open-chain benzyl β-oxo esters, has been studied. When carried out in the presence of catalytic amounts of cinchonine, the reaction gave optically active α-aryl ketones with up to 75% ee. Enantio-enriched (S)-3-phenyl-2-butanone can be converted into 2-phenylpropionic acid without racemisation. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Baker's yeast reduction of α-methyleneketones

The bioreduction of α-methyleneketones, R1C(=O)C(=CH2)R2 (R1 = Me, Et, Pr, iso-Bu, Ph, CH2CH2Ph; R2 = Cl, Me, Et, n-Pr, iso-Pr, n-Bu, n-C6H13, Ph, CH2Ph), was mediated by baker's yeast (Saccharomyces cerevisiae) to obtain the corresponding α-methylketones. The R1 and R2 groups had a significant influence on the rate and enantioselectivity of the reductions. The rate of C=C bond reduction was higher than that of C=O bond reduction. Only α-methyleneketones having R1 = Me yielded α-methylketones in high enantioselectivity with e.e.s of 88-99%.