181185-39-7

Basic information

• Product Name: 2-Hexanone, 4-hydroxy-, (S)- (9CI)
• Synonyms: 2-Hexanone, 4-hydroxy-, (S)- (9CI)
• CAS NO: 181185-39-7
• Molecular Formula: C6H12O2
• Molecular Weight: 116.15828
• Product Categories: ACETYLGROUP
• Mol File: 181185-39-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Hexanone, 4-hydroxy-, (S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hexanone, 4-hydroxy-, (S)- (9CI)(181185-39-7)
• EPA Substance Registry System: 2-Hexanone, 4-hydroxy-, (S)- (9CI)(181185-39-7)

Safety Data

• Hazardous Substances Data: 181185-39-7(Hazardous Substances Data)

Upstream product

• 66536-78-5 (+)-(R)-1-(p-tolylsulfinyl)-2-propanone 
• 123-38-6 propionaldehyde 
• 97169-20-5 N,N-Dimethyl-N'-[1-methyl-2-((R)-toluene-4-sulfinyl)-eth-(E)-ylidene]-hydrazine 
• 67-64-1 acetone 
• 917-64-6 methyl magnesium iodide 

Relevant articles and documents

Method for synthesizing beta-hydroxy carbonyl compound by catalyzing asymmetric Aldol reaction in water phase

The invention discloses a method for synthesizing a beta-hydroxy carbonyl compound by catalyzing asymmetric Aldol reaction in a water phase. The method comprises the following steps: in the water phase, catalyzing ketone and aldehyde with equal molar weig

Synthesis of Enantiomerically Pure β-Hydroxy Ketones via β-Keto Weinreb Amides by a Condensation/Asymmetric-Hydrogenation/Acylation Sequence

An established route to enantiomerically pure β-hydroxy ketones proceeds through the asymmetric hydrogenation of β-keto esters, an ester/amide exchange, and the use of the resulting β-hydroxy amide for the acylation of an organometallic compound. We shortened this route by showing that β-keto Weinreb amides are hydrogenated with up to 99 % ee in the presence of [Me2NH2]+{[RuCl(S)-BINAP]2(μ-Cl)3}–(0.5 mol-%) at room temp./5 bar. These Weinreb amides were prepared by seemingly obvious yet unprecedented condensations of lithiated N-methoxy-N-methylacetamide with carboxylic chlorides (51–87 % yield). The resulting β-hydroxy Weinreb amides were used for the acylation of organolithium and Grignard reagents. They thus gave enantiomerically pure β-hydroxy ketones (28 examples). A selection of these compounds gave anti-1,3-diols after another C=O bond hydrogenation, or syn-1,3-diols by a Narasaka–Prasad reduction.

Contrasting steric effects of the ketones and aldehydes in the reactions of the diisopinocampheyl enolborinates of methyl ketones with aldehydes

Treatment of the diisopinocampheylborinates of a representative series of methyl ketones with a representative series of aldehydes, both of differing steric requirements provides aldols whose enantiomeric purifies depend on the steric requirements of both the ketones and the aldehydes. This study has shown that increasing the steric requirements of the R group in the ketones has a pernicious effect on the ee, while increasing the steric requirements of the R group in the aldehydes exerts a beneficial effect on the ee.

Preparation of Chiral β-Hydroxyketones by Aldol-type Condensation of Chiral p-Tolylsulfinylmethyl Ketones

Chiral β-hydroxyketones 7 with fair e.e. were prepared by treating newly prepared optically pure p-tolylsulfinylmethyl ketones 4 with t-butylmagnesium bromide and aldehydes 5 followed by desulfurization with aluminium amalgam.

C-C ASYMMETRIC BOND FORMATION MEDIATED BY OPTICALLY ACTIVE SULFOXIDES

Highly stereoselective C-C bond forming reactions can be performed with a variety of optically active sulfinyl derivatives to afford, after desulfurization, optically active sulfur-free products.