470693-88-0Relevant academic research and scientific papers
Explorations of [4+2] and [5+2] cycloadditions of dienylcyclopropane derived enzymatically from cyclopropylbenzene
Hudlicky, Jason Reed,Hopkins-Hill, John,Hudlicky, Tomas
supporting information; experimental part, p. 2891 - 2895 (2012/01/06)
Fermentation of cyclopropylbenzene with E. coli JM109(pDTG601a) furnished optically pure 1-cyclopropyl-2,3-dihydroxycyclohexa-4,6-diene whose reactivity in [4+2]- and [5+2]-cycloaddition chemistry was explored. Georg Thieme Verlag Stuttgart. New York.
Processing of cyclopropylarenes by toluene dioxygenase: Isolation and absolute configuration of metabolites
Finn, Kevin J.,Rochon, Lena,Hudlicky, Tomas
, p. 3606 - 3613 (2007/10/03)
Several arenes possessing a cyclopropyl substituent were subjected to enzymatic oxidation with toluene dioxygenase. The absolute configuration of metabolites was established by chemical means.
Enzymatic oxidation of cyclopropylbenzene: Structures of new metabolites and possible mechanistic implications
Bui, Vu P.,Nguyen, Minh,Hansen, Jeff,Baker, John,Hudlicky, Tomas
, p. 708 - 713 (2007/10/03)
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.
