176166-10-2

Basic information

• Product Name: (+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene
• Synonyms: (+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene
• CAS NO: 176166-10-2
• Molecular Weight: 297.974
• Mol File: 176166-10-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene(176166-10-2)
• EPA Substance Registry System: (+)-(1S,2R)-1-acetoxy-2,3-dibromocyclohex-3-ene(176166-10-2)

Safety Data

• Hazardous Substances Data: 176166-10-2(Hazardous Substances Data)

Upstream product

• 40635-67-4 acetoxyisobutyryl bromide 
• 174817-06-2 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohex-3-ene 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 

Downstream Products

• 71942-12-6 2-bromo-1a,5a-dihydro-1-benzoxirene 
• 1431975-75-5 (-)-(1S)-1-hydroxy-3-bromocyclohexa-2,4-diene 
• 1498378-85-0 (1S,4S)-3-bromo-4-(p-toluenesulfonamido)cyclohex-2-enyl acetate 

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.