105928-96-9

Basic information

• Product Name: (1R,2S)-1-methyl-1,2-cyclohexanediol
• Synonyms: (1R,2S)-1-methyl-1,2-cyclohexanediol
• CAS NO: 105928-96-9
• Molecular Weight: 130.187
• Mol File: 105928-96-9.mol
• Article Data: 30

Chemical Properties

• CAS DataBase Reference: (1R,2S)-1-methyl-1,2-cyclohexanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-1-methyl-1,2-cyclohexanediol(105928-96-9)
• EPA Substance Registry System: (1R,2S)-1-methyl-1,2-cyclohexanediol(105928-96-9)

Safety Data

• Hazardous Substances Data: 105928-96-9(Hazardous Substances Data)

Upstream product

• 19324-75-5 2-chloro-1-methylcylohexanol 
• 591-49-1 1-methylcyclohex-1-ene 
• 1713-33-3 1,2-epoxy-1-methylcyclohexane 
• 63703-34-4 2,2-dimethoxycyclohexanol 
• 96304-40-4 (R)-(+)-2-hydroxy-2-methylcyclohexanone 
• 52718-65-7 1-methyl-1,2-cyclohexanediol 
• 82166-21-0 methyl cyclohexane 
• 590-67-0 1-Methylcyclohexanol 
• 591-47-9 4-methylcyclohexene 
• 4065-80-9 2-methylenecyclohexanol 
• 4892-02-8 Methyl thiosalicylate 
• 1126-81-4 4-acetamidothiophenol 
• 137-07-5 2-amino-benzenethiol 
• 1074-36-8 4-mercaptobenzoic acid 

Downstream Products

• 583-60-8 2-Methylcyclohexanone 
• 6140-63-2 1-methyl-1-cyclopentanecarbaldehyde 
• 19324-75-5 2-chloro-1-methylcylohexanol 
• 96304-02-8 2-hydroxy-2-methylcyclohexanone 
• 3128-07-2 6-oxoheptanoic acid 
• 81455-05-2 trans-1-Methyl-2-phenoxycyclohexan-1-ol 
• 90-27-7 2-Phenylbutyric acid 
• 118907-66-7 2-Phenyl-butyric acid (1S,2R)-2-hydroxy-2-methyl-cyclohexyl ester 
• 118907-66-7 2-Phenyl-butyric acid (1R,2R)-2-hydroxy-2-methyl-cyclohexyl ester 
• 54826-46-9 (+/-)-1,2c-dibenzoyloxy-1r-methyl-cyclohexane 
• 16749-63-6 (+/-)-1r,2t-diacetoxy-1-methyl-cyclohexane 

Relevant articles and documents

ASYMMETRIC OXIDATION OF OLEFINS TO VICINAL DIOLS WITH OSMIUM TETROXIDE

High levels of asymmetry can be achieved in the osmium tetroxide cis-hydroxylation of olefins by employing (-)-(R,R)-N,N,N',N'-tetramethylcyclohexane-1,2-trans-diamine as a chiral ligand for the osmium.

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Catalytic asymmetric dihydroxylation of olefins using a recoverable and reusable OsO42- in ionic liquid [bmim][PF6]

The use of the solvent systems water/ionic liquid or water/ionic liquid/tert-butanol provides a recoverable, reusable, robust and simple system for the asymmetric dihydroxylation of olefins, based on the immobilization of the osmium-ligand catalyst in the ionic liquid phase.

Chemoenzymic resolution and deracemisation of (±)-1-methyl-1,2- epoxycyclohexane: The synthesis of (1-S, 2-S)-1-methylcyclohexane-1,2-diol

Corynebacterium C12 epoxide hydrolase transforms (±)-1-methyl-1,2-epoxy-cyclohexane 1 to the (1-S, 2-S)-1-methylcyclohexane-1,2-diol 2 leaving the (1-S, 2-R)-epoxide 3 unchanged. The diol 2 is converted to the (1-R, 2-S)-epoxide 4 by sulfonation-ring closure. A one pot combination of Corynebacterium C12 epoxide hydrolase and acid catalysed ring opening converts (±)-1-methyl-1,2-epoxycyclohexane 1 to (1-S, 2-S)-1-methylcyclohexane-1,2-diol 2.

Acid-catalyzed enzymatic hydrolysis of 1-methylcyclohexene oxide

Limonene-1,2-epoxide hydrolase from Rhodococcus erythropolis DCL14, an enzyme involved in the limonene metabolism of this microorganism, catalyzes the enantioselective hydrolysis of 1-methylcyclohexene oxide. (1R,2S)-1- Methylcyclohexene oxide was the preferred substrate and it was mainly hydrolyzed to (1S,2S)-1-methylcyclohexane-1,2-diol, while (1S,2R)-1- methylcyclohexene oxide was converted more slowly and mainly yielded (1R,2R)- 1-methylcyclohexane-1,2-diol. The reaction proceeded with a high regioselectivity (C1:C2, 85:15). H218O-labelling experiments confirmed that the nucleophile was mainly incorporated at the most substituted carbon atom, suggesting that limonene-1,2-epoxide hydrolase uses an acid-catalyzed enzyme mechanism.

Efficient photocatalytic oxidation of cycloalkenes by dihydroxo(tetraphenylporphyrinato)-antimony supported on silica gel under visible light irradiation

In order to develop a photocatalyst operating under visible light irradiation, silica gel-supported dihydroxo(tetraphenylporphyrinato)antimony (V) complex, [SbTPP(OH)2]+/SiO2, was prepared. The photocatalytic oxidation of cycloalkenes with oxygen molecule was performed on [SbTPP(OH)2]+/SiO2 particles under irradiation of fluorescent light. The photocatalytic oxidation of cycloalkenes gave the corresponding cis-1,2-epoxycycloalkane, 2-cycloalkene-1-ol, and trans-1,2-cycloalkanediol.

A Change from Kinetic to Thermodynamic Control Enables trans-Selective Stereochemical Editing of Vicinal Diols

Here, we report the selective, catalytic isomerization of cis-1,2-diols to trans-diequatorial-1,2-diols. The method employs triphenylsilanethiol (Ph3SiSH) as a catalyst and proceeds under mild conditions in the presence of a photoredox catalyst and under

Hydrodealkenylative C(sp3)–C(sp2) bond fragmentation

Chemical synthesis typically relies on reactions that generate complexity through elaboration of simple starting materials. Less common are deconstructive strategies toward complexity—particularly those involving carbon-carbon bond scission. Here, we introduce one such transformation: the hydrodealkenylative cleavage of C(sp3)–C(sp2) bonds, conducted below room temperature, using ozone, an iron salt, and a hydrogen atom donor. These reactions are performed in nonanhydrous solvents and open to the air; reach completion within 30 minutes; and deliver their products in high yields, even on decagram scales. We have used this broadly functionality tolerant transformation to produce desirable synthetic intermediates, many of which are optically active, from abundantly available terpenes and terpenoid-derived precursors. We have also applied it in the formal total syntheses of complex molecules.