176166-15-7

Basic information

• Product Name: 3-Cyclohexene-1,2-diol, 3-chloro-, (1S,2S)-
• CAS NO: 176166-15-7
• Molecular Formula: C6H9ClO2
• Molecular Weight: 148.589
• Mol File: 176166-15-7.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 3-Cyclohexene-1,2-diol, 3-chloro-, (1S,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1,2-diol, 3-chloro-, (1S,2S)-(176166-15-7)
• EPA Substance Registry System: 3-Cyclohexene-1,2-diol, 3-chloro-, (1S,2S)-(176166-15-7)

Safety Data

• Hazardous Substances Data: 176166-15-7(Hazardous Substances Data)

Upstream product

• 86992-79-2 (1S,2S)-3-Chloro-cyclohexa-3,5-diene-1,2-diol 

Downstream Products

• 1569135-06-3 (1S,2R)-2,3-dichlorocyclohex-3-enol 
• 1498378-66-7 (1S,2R)-2-azido-3-chlorocyclohex-3-enol 
• 1498378-67-8 (1S,4S)-4-azido-3-chloro-3-cyclohexen-1-ol 
• 1569135-02-9 (1S,2R)-2,3-dichlorocyclohex-3-en-1-yl sulfochloridate 
• 1431975-48-2 (+)-(1S,2R)-1-acetoxy-2-bromo-3-chlorocyclohex-3-ene 
• 1392229-39-8 (4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-3-chlorocyclohex-2-en-1-one 
• 1392229-29-6 (4S,5S)-3-chloro-4,5-dihydroxycyclohex-2-enone 
• 426206-55-5 {[(1S,2S)-3-chloro-3-cyclohexene-1,2-diyl]bis(oxy)}bis[(1,1-dimethylethyl)dimethylsilane] 
• 1228121-64-9 (1S,2S)-1-benzyloxy-3-chlorocyclohex-3-en-2-ol 
• 1228121-63-8 (1S,2S)-2-benzyloxy-3-chlorocyclohex-3-en-1-ol 
• 828295-37-0 trans-(1S,2R)-1,2-dihydroxy-3-chlorocyclohex-3-ene 
• 929619-83-0 trans-(1S,2R)-1,2-diacetoxy-3-chloro-5-bromocyclohex-3-ene 
• 929619-77-2 trans-(1S,2R)-1,2-diacetoxy-3-chlorocyclohex-3-ene 
• 929619-90-9 trans-(1S,2R)-1,2-diacetoxy-3-chlorocyclohexa-3,5-diene 

Relevant articles and documents

Chemoenzymatic synthesis of monocyclic arene oxides and arene hydrates from substituted benzene substrates

Enantiopure cis-dihydrodiol bacterial metabolites of substituted benzene substrates were used as precursors, in a chemoenzymatic synthesis of the corresponding benzene oxides and of a substituted oxepine, via dihydrobenzene oxide intermediates. A rapid total racemization of the substituted benzene 2,3-oxides was found to have occurred, via their oxepine valence tautomers, in accord with predictions and theoretical calculations. Reduction of a substituted arene oxide to yield a racemic arene hydrate was observed. Arene hydrates have also been synthesised, in enantiopure form, from the corresponding dihydroarene oxide or trans-bromoacetate precursors. Biotransformation of one arene hydrate enantiomer resulted in a toluene-dioxygenase catalysed cis-dihydroxylation to yield a benzene cis-triol metabolite. The Royal Society of Chemistry 2013.

Cycloalkenyl halide substitution reactions of enantiopure arene cis-tetrahydrodiols with boron, nitrogen and phosphorus nucleophiles

Enantiopure arene cis-tetrahydrodiols of bromobenzene and iodobenzene have been obtained in good yields, from chemoselective hydrogenation (rhodium-graphite) of the corresponding cis-dihydrodiol metabolites. Palladium-catalysed substitution of the halogen, by hydrogen, boron, nitrogen and phosphorus nucleophiles, in the acetonide derivatives, has yielded highly functionalised products for application in synthesis with potential as scaffolds for chiral ligands. Copyright

Chemoenzymatic synthesis of trans-dihydrodiol derivatives of monosubstituted benzenes from the corresponding cis-dihydrodiol isomers

Enantiopure trans-dihydrodiols have been obtained by a chemoenzymatic synthesis from the corresponding cis-dihydrodiol metabolites, obtained by dioxygenase-catalysed arene cis-dihydroxylation at the 2,3-bond of monosubstituted benzene substrates. This gen