174817-06-2

Basic information

• Product Name: 3-Cyclohexene-1,2-diol, 3-bromo-, (1S,2S)-
• CAS NO: 174817-06-2
• Molecular Formula: C6H9BrO2
• Molecular Weight: 193.04
• Mol File: 174817-06-2.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: 3-Cyclohexene-1,2-diol, 3-bromo-, (1S,2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1,2-diol, 3-bromo-, (1S,2S)-(174817-06-2)
• EPA Substance Registry System: 3-Cyclohexene-1,2-diol, 3-bromo-, (1S,2S)-(174817-06-2)

Safety Data

• Hazardous Substances Data: 174817-06-2(Hazardous Substances Data)

Upstream product

• 130669-75-9 (3aS,7aS)-4-bromo-2,2-dimethyl-3a,7a-dihydro-1,3-benzodioxole 
• 108-86-1 bromobenzene 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 

Downstream Products

• 1358516-96-7 (1S,6S)-2-bromo-6-(tert-butyldiphenylsilyloxy)cyclohex-2-enol 
• 1358516-98-9 [[(1S,4R)-3-bromo-4-(diphenylphosphoryl)cyclohex-2-en-1-yl]oxy](tert-butyl)diphenylsilane 
• 1358517-02-8 (1S,4R)-3-diphenylphosphino-4-diphenylphosphoryl-cyclohex-2-enyloxy(tert-butyl)diphenylsilane 
• 1370320-05-0 (+)-tert-butyl N-[(1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-(6-chloropyridin-3-yl)cyclohex-2-en-1-yl]carbamate 
• 1370320-06-1 (+)-tert-butyl N-[(1R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohex-2-en-1-yl]carbamate 
• 211503-91-2 (-)-tert-butyl N-[(1R,2R,4S)-2-(6-chloropyridin-3-yl)-4-hydroxycyclohexyl]carbamate 
• 211503-92-3 N-[(1R,2R,4R)-4-bromo-2-(6-chloro(3-pyridyl))cyclohexyl](tert-butoxy)carboxamide 
• 217323-82-5 (1R,2R,4R)-4-bromo-2-(6-chloropyridin-3-yl)cyclohexanamine 
• 1370320-08-3 (+)-tert-butyl (1R,4S)-2-bromo-4-hydroxycyclohex-2-enylcarbamate 
• 455330-42-4 4R-(4-oxocyclohex-2-enyl)carbamic acid tert-butyl ester 
• 1370320-03-8 C₁₃H₂₄BrNO₃Si 
• 1370320-04-9 (+)-tert-butyl N-[(1R,4S)-2-bromo-4-[(tert-butyldimethylsilyl)oxy]cyclohex-2-en-1-yl]carbamate 
• 1569135-07-4 (1S,2R)-3-bromo-2-chlorocyclohex-3-enol 
• 1569135-03-0 (1S,2R)-3-bromo-2-chlorocyclohex-3-en-1-yl sulfochloridate 

Relevant articles and documents

Chemoenzymatic synthesis of trans -tetrahydrofuran cores of annonaceous acetogenins from bromobenzene

Two types of trans-THF cores, present in acetogenins, have been synthesized by an intramolecular iodoetherification reaction. The starting alkenol was obtained in a few steps from a chiral cis-diol resulting from microbial oxidation of bromobenzene. The cyclization gave complete stereoselectivity for trans-THF cores with either (S,S) or (R,R) configurations at the THF chiral carbons.

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.

Chemoenzymatic formal synthesis of (-)- and (+)-epibatidine

The cis-dihydrocatechol, derived from enzymatic cis-dihydroxylation of bromobenzene using the microorganism Pseudomonas putida UV4, was converted into (-)-epibatidine in eleven steps with complete stereocontrol. In addition, an unprecedented palladium-catalysed disproportionation reaction gave the (+)-enantiomer of an advanced key intermediate employed in a previous synthesis of epibatidine.