470693-90-4

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 academic research and scientific papers

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.

Processing of cyclopropylarenes by toluene dioxygenase: Isolation and absolute configuration of metabolites

Several arenes possessing a cyclopropyl substituent were subjected to enzymatic oxidation with toluene dioxygenase. The absolute configuration of metabolites was established by chemical means.