114763-28-9

Basic information

• Product Name: 3,5-Cyclohexadiene-1,2-diol, 3-ethenyl-, (1S,2R)-
• CAS NO: 114763-28-9
• Molecular Formula: C8H10O2
• Molecular Weight: 138.166
• Mol File: 114763-28-9.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 3,5-Cyclohexadiene-1,2-diol, 3-ethenyl-, (1S,2R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Cyclohexadiene-1,2-diol, 3-ethenyl-, (1S,2R)-(114763-28-9)
• EPA Substance Registry System: 3,5-Cyclohexadiene-1,2-diol, 3-ethenyl-, (1S,2R)-(114763-28-9)

Safety Data

• Hazardous Substances Data: 114763-28-9(Hazardous Substances Data)

Upstream product

• 591-50-4 iodobenzene 
• 108-86-1 bromobenzene 
• 100-42-5 styrene 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 

Relevant articles and documents

Site-Directed Mutagenesis Studies on the Toluene Dioxygenase Enzymatic System: Role of Phenylalanine 366, Threonine 365 and Isoleucine 324 in the Chemo-, Regio-, and Stereoselectivity

Toluene Dioxygenase (TDO) enzymatic complex has been widely used as a biocatalyst for the regio- and enantioselective preparation of cis-cyclohexadienediols, which are very important starting materials for organic synthesis. However, the lack of regio- and stereodiversity of the dioxygenation process by TDO and related dioxygenases constitutes a clear drawback when planning the use of these diols in synthetic schemes. In this work, we developed three TDO mutants in residues phenylalanine 366, threonine 365 and isoleucine 324, with the aim to alter the chemo-, regio- and stereoselectivity of the biotransformation of arenes. While no changes in the regioselectivity of the process were observed, dramatic variations in the chemo- and enantioselectivity were found for mutants I324F, T365N and F366 V in a substrate-dependent manner. (Figure presented.).

Medium-scale preparation of useful metabolites of aromatic compounds via whole-cell fermentation with recombinant organisms

The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10-15L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.

New Diol Metabolites Derived by Biooxidation of Chlorostyrenes with Pseudomonas putida: Determination of Absolute Stereochemistry and Enantiomeric Excess by Convergent Syntheses

The three isomers of chlorostyrenes were subjected to whole cell biooxidation by means of a mutant strain of Pseudomonas putida 39D.The metabolites were isolated and their absolute stereochemistry determined by conversion to known standards derived from 1-ethenyl-2,3-dihydroxycyclohexa-4,6-diene whose absolute configuration has been previously established.The extent of ring vs side chain oxidation of the chlorostyrene isomers was evaluated and the enantiomeric excess determined for all compounds.