114818-70-1

Basic information

• Product Name: (R)-α-hydroxycyclohexanone
• CAS NO: 114818-70-1
• Molecular Weight: 114.144
• Mol File: 114818-70-1.mol

Chemical Properties

• CAS DataBase Reference: (R)-α-hydroxycyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-α-hydroxycyclohexanone(114818-70-1)
• EPA Substance Registry System: (R)-α-hydroxycyclohexanone(114818-70-1)

Safety Data

• Hazardous Substances Data: 114818-70-1(Hazardous Substances Data)

Upstream product

• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 
• 147168-86-3 (2R,4R,7R)-2,4-Dimethyl-1,5-dioxa-spiro[5.5]undecan-7-ol 
• 931-57-7 1-methoxy-cyclohex-1-ene 
• 108-94-1 cyclohexanone 
• 627106-80-3 (7β,11β)-3,3-dimethyl-7,11-diphenyl-2,4-dioxaspiro[5.5]undecane-1,5,9-trione 
• 533-60-8 cyclohexanone-2-ol 
• 286-20-4 cyclohexane-1,2-epoxide 
• 765-87-7 cyclohexane-1,2-dione 
• 1792-81-0 cis-1,2-cyclohexane 
• 1460-57-7 trans-1,2-cyclohexandiol 
• 1072-21-5 hexanedial 
• 1638623-52-5 (cyclohex-1-en-1-yloxy)dimethylsilanol 
• 58101-72-7 C₈H₁₅ClOSi 
• 1161819-40-4 (R)-2-(2-tolylaminooxy)cyclohexanone 

Downstream Products

• 1792-81-0 cis-1,2-cyclohexane 
• 1072-86-2 (1R,2R)-trans-1,2-cyclohexanediol 

Relevant articles and documents

Selective Oxidation of Optically Active sec,sec-1,2-Diols by Dioxiranes. A Practical Method for the Synthesis of Homochiral α-Hydroxy Ketones in High Optical Purity

By employing either dimethyldioxirane or its trifluoromethyl analog, the direct, high-yield conversion of one cyclic and three open chain optically sec,sec-1,2-diols to the corresponding α-hydroxy ketones in high optical yield has been achieved.

Isoquinolinium dichromate: A new and selective oxidant for primary and secondary alcohols

Isoquinolinium clichromate is a new versatile reagent for selective oxidation of primary and secondary alcohols under mild conditions. It also oxidises vicinal and nonvicinal diols to the corresponding α-hydroxy carbonyl compounds.

Site-Selective and Product Chemoselective Aliphatic C-H Bond Hydroxylation of Polyhydroxylated Substrates

Site-selective and product chemoselective aliphatic C-H bond oxidation of 1,2-diols and of polyhydroxylated substrates using iron and manganese catalysts and hydrogen peroxide as terminal oxidant is described. The reaction capitalizes on the use of fluorinated alcohol solvents such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP), which exert a strong polarity reversal in the hydroxyl moieties of 1,2-diols via hydrogen bonding, in turn translating into a strong deactivation of proximal C-H bonds against a HAT initiated oxidation by the putative high-valent and electrophilic metal-oxo species. As a result, site-selective and product chemoselective oxidation of complex polyfunctional molecules such as steroids, sugars, and pharmaceuticals is described, where exclusive or predominant C-H bond hydroxylation at a remote and nonactivated site takes place. The current report discloses HAT initiated hydroxylations in fluorinated alcohol solvents as methods displaying orthogonal chemoselectivity to contemporary alcohol oxidations providing a useful tool for synthetic planning in densely functionalized molecules.

Electroenzymatic Oxidation of Alcohols on a Poly(acrylic acid)-coated Graphite Felt Electrode Terimmobilizing Ferrocene, Diaphorase and Alcohol Dehydrogenase

A preparative electroenzymatic oxidation of alcohols was successfully carried out on a poly(acrylic acid)-coated graphite felt electrode ter-immobilizing ferrocene, diaphorase and alcohol dehydrogenase in the domain of the poly(acrylic acid) layer in a 1 mM NADH / phosphate buffer (pH 7.2) with high stereoselectivity (> 96percent), high isolated yield (> 90percent) and high current efficiency (>89percent).

Diastereoface-differentiating oxidation of 1-cyclohexenyl ether using a 2,4-pentanediol tether

Diastereoface-differentiating oxidation of the chiral enol ether prepared from cyclohexanone and optically active 2,4-pentanediol gave a diastereomeric mixture of the corresponding 2-hydroxycyclohexanone acetal. The diastereomeric excess of the product reached over 99% by oxidation with m-chloroperbenzoic acid at -78°C. Oxidation with t-butyl hydroperoxide in the presence of metal catalysts also resulted in high diastereomeric excesses of up to 97%.

Chemoenzymatic synthesis of α′- And α-acetoxylated cyclic ketones

α,β-Unsaturated and saturated cyclic ketones were selectively oxidized at the α′- and α-positions using Mn(OAc)3 and Pb(OAc)4, respectively, resulting in high chemical yields. The resultant racemic α′- and α-acetoxylated substrates were resolved into corresponding enantiomerically enriched α′- and α-hydroxylated and acetoxylated compounds with 96-98% ee via PLE hydrolysis. The absolute configurations of α′-acetoxy-α,β-unsaturated cyclic ketones were determined by transforming them into the corresponding saturated α-acetoxy cyclic ketones of known absolute configuration.

Diastereoface Differentiating Peracid Oxidation of the Enol Ether Derived from Cyclohexanone and 2,4-Pentanediol: Preparation of Optically Pure 2-Hydroxycyclohexanone Acetal

Diastereoface differentiating m-chloroperbenzoic acid oxidation of the chiral enol ether prepared from cyclohexanone and optically active 2,4-pentanediol proceeded from -72 to 39 deg C to give a diastereomeric mixture of the corresponding 2-hydroxycyclohexanone acetal.The diastereomeric excess of the product reached almost 100 percent at -72 deg C.

SYNTHESIS AND APPLICATION OF CHIRAL SUBSTITUTED POLYVINYLPYRROLIDINONES

Chiral polyvinylpyrrolidinone (CSPVP), complexes of CSPVP with a core species, such as a metallic nanocluster catalyst, and enantioselective oxidation reactions utilizing such complexes are disclosed. The CSPVP complexes can be used in asymmetric oxidation of diols, enantioselective oxidation of alkenes, and carbon-carbon bond forming reactions, for example. The CSPVP can also be complexed with biomolecules such as proteins, DNA, and RNA, and used as nanocarriers for siRNA or dsRNA delivery.

One-Pot Enzymatic Synthesis of Cyclic Vicinal Diols from Aliphatic Dialdehydes via Intramolecular C?C Bond Formation and Carbonyl Reduction Using Pyruvate Decarboxylases and Alcohol Dehydrogenases

An enzymatic cascade reaction was developed for one-pot enantioselective conversion of aliphatic dialdehydes to chiral vicinal diols using pyruvate decarboxylases (PDCs) and alcohol dehydrogenases (ADHs). The PDCs showed promiscuity in catalysing the cyclization of aliphatic dialdehydes through intramolecular stereoselective carbon-carbon bond formation. Consequently, 1,2-cyclopentanediols in three different stereoisomeric forms and 1,2-cyclohexanediols in two different stereoisomeric forms could be prepared with high conversion and stereoisomeric ratio from the respective initial substrates, glutaraldehyde and adipaldehyde. These cascade reactions represent a promising approach to the biocatalytic synthesis of important chiral vicinal diols. (Figure presented.).

Regio- and enantioselective reduction of diketones: Preparation of enantiomerically pure hydroxy ketones catalysed by Candida parapsilosis ATCC 7330

Enantiomerically enriched hydroxy ketones were prepared by the reduction of the corresponding diketones with excellent enantiomeric excess (98%) and in good yields (up to 75%) using whole cells of Candida parapsilosis ATCC 7330. Cyclic diketones, such as 1,2-cyclohexanedione and 1,4-cyclohexanedione, resulted in hydroxy ketones as products. Cyclohexane-1,3-dione and 5,5-dimethylcyclohexane-1,3-dione gave dimerised products, such as 2,2′-(ethane-1,1-diyl)bis(3-hydroxycyclohex-2-enone) and 2,2′-(ethane-1,1-diyl)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) with acetaldehyde generated in situ from whole cells of Candida parapsilosis ATCC 7330, which is reported here for the first time.