951-85-9

Basic information

• Product Name: 1-Propanone, 1,2-diphenyl-, (S)-
• CAS NO: 951-85-9
• Molecular Formula: C15H14O
• Molecular Weight: 210.276
• Mol File: 951-85-9.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: 1-Propanone, 1,2-diphenyl-, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Propanone, 1,2-diphenyl-, (S)-(951-85-9)
• EPA Substance Registry System: 1-Propanone, 1,2-diphenyl-, (S)-(951-85-9)

Safety Data

• Hazardous Substances Data: 951-85-9(Hazardous Substances Data)

Usage

Enantiomer

1-phenyl-1,2-propanedione

Uses

Chiral building block in organic synthesis (preparation of pharmaceuticals, agrochemicals, and other fine chemicals), chiral auxiliary in asymmetric synthesis, fragrance ingredient in perfumes and cosmetics

Physical properties

Yellow to brownish liquid, sweet and floral odor

Stability

Relatively stable under normal conditions

Upstream product

• 25145-43-1 (2S)-2-phenylpropionyl chloride 
• 2674-04-6 diphenyl cadmium 
• 14037-02-6 2-(2-phenyl-propenyl)-pyridine 
• 1832-41-3 2-bromo-1,2-diphenyl-propan-1-one 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 144930-50-7 mesityl(phenyl)iodonium triflouromethanesulfonate 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 22293-10-3 (1-diazoethyl)benzene 
• 100-52-7 benzaldehyde 
• 13466-30-3 (1-phenylethylidene)hydrazine 
• 100-58-3 phenylmagnesium bromide 
• 46755-94-6 (S)-1,1-diphenyl-1,2-propanediol 
• 195832-80-5 (R)-1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-2-phenyl-propan-1-one 
• 129505-03-9 (2R)-N-(phenylacetyl)bornane-10,2-sultam 

Downstream Products

• 100-42-5 styrene 
• 18220-90-1 4-ethylbenzophenone 
• 2042-85-5 1,2-diphenylpropan-1-one 
• 100-52-7 benzaldehyde 
• 58751-83-0 1,2-diphenylpropan-1-one 
• 1857-74-5 2,3-diphenylbutane 
• 19643-70-0 (2R)-propane-1,2-diyldibenzene 
• 89103-75-3 (1R,2S)-1,2-diphenylpropan-1-ol 
• 89103-72-0 (1S,2S)-1,2-diphenylpropan-1-ol 

Relevant articles and documents

Enantioselective decarboxylative protonation and deuteration of β-ketocarboxylic acids

Enantioselective decarboxylative protonation of tetralone-derived β-ketocarboxylic acids was achieved with up to 89% enantiomeric excess (ee)-in the presence of a chiral primary amine catalyst. Furthermore, this method was applied to enantioselective deuteration to afford the corresponding α-deuterioketones with up to 88% ee.

Enantioselective α-Arylation of Ketones via a Novel Cu(I)-Bis(phosphine) Dioxide Catalytic System

A novel catalytic system based on copper(I) and chiral bis(phosphine) dioxides is described. This allows the arylation of silyl enol ethers to access enolizable α-arylated ketones in good yields and enantiomeric excess up to 95%. Noncyclic ketones are amenable substrates with this method, which complements other approaches based on palladium catalysis. Optimization of the ligand structure is accomplished via rational design driven by correlation analysis. Preliminary mechanistic hypotheses are also evaluated in order to identify the role of chiral bis(phosphine) dioxides.

Mechanistic Investigation of Enantioconvergent Kumada Reactions of Racemic α-Bromoketones Catalyzed by a Nickel/Bis(oxazoline) Complex

In recent years, a wide array of methods for achieving nickel-catalyzed substitution reactions of alkyl electrophiles by organometallic nucleophiles, including enantioconvergent processes, have been described; however, experiment-focused mechanistic studies of such couplings have been comparatively scarce. The most detailed mechanistic investigations to date have examined catalysts that bear tridentate ligands and, with one exception, processes that are not enantioselective; studies of catalysts based on bidentate ligands could be anticipated to be more challenging, due to difficulty in isolating proposed intermediates as a result of instability arising from coordinative unsaturation. In this investigation, we explore the mechanism of enantioconvergent Kumada reactions of racemic α-bromoketones catalyzed by a nickel complex that bears a bidentate chiral bis(oxazoline) ligand. Utilizing an array of mechanistic tools (including isolation and reactivity studies of three of the four proposed nickel-containing intermediates, as well as interrogation via EPR spectroscopy, UV-vis spectroscopy, radical probes, and DFT calculations), we provide support for a pathway in which carbon-carbon bond formation proceeds via a radical-chain process wherein a nickel(I) complex serves as the chain-carrying radical and an organonickel(II) complex is the predominant resting state of the catalyst. Computations indicate that the coupling of this organonickel(II) complex with an organic radical is the stereochemistry-determining step of the reaction.