470693-90-4

Basic information

• Product Name: 3-Cyclohexene-1,2-diol, 3-cyclopropyl-, (1S,2R)-
• CAS NO: 470693-90-4
• Molecular Formula: C9H14O2
• Molecular Weight: 154.209
• Mol File: 470693-90-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-Cyclohexene-1,2-diol, 3-cyclopropyl-, (1S,2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Cyclohexene-1,2-diol, 3-cyclopropyl-, (1S,2R)-(470693-90-4)
• EPA Substance Registry System: 3-Cyclohexene-1,2-diol, 3-cyclopropyl-, (1S,2R)-(470693-90-4)

Safety Data

• Hazardous Substances Data: 470693-90-4(Hazardous Substances Data)

Upstream product

• 174953-42-5 (3aS,7aS)-7-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole 
• 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 
• 873-49-4 cyclopropylbenzene 
• 100-42-5 styrene 
• 470693-89-1 7-cyclopropyl-2,2-dimethyl-3a,4,5,7a-tetrahydrobenzo[1,3]dioxole 
• 470693-88-0 3-cyclopropylcyclohexa-3,5-diene-1,2-diol 

Relevant articles and documents

Enzymatic oxidation of cyclopropylbenzene: Structures of new metabolites and possible mechanistic implications

Cyclopropylbenzene was subjected to whole-cell fermentation with either Escherichia coli JM109 (pDTG601) or E. coli JM109 (pDTG602), expressing toluene dioxygenase and toluene dioxygenase - dihydrodiol dehydrogenase enzymes, respectively. The corresponding metabolites, 3-cyclopropylcyclohexa-3,5-diene-1,2-diol (3) and 3-cyclopropylbenzene-1,2-diol (5) have been isolated in yields of 2.5 and 1 g L-1, respectively. The absolute stereochemistry correlation for 3 is provided, along with a preliminary discussion of its potential in asymmetric synthesis. Possible mechanistic implications are indicated for the enzymatic oxygenation through the use of calculations. Experimental data are provided for all new compounds.