114763-29-0

Basic information

• Product Name: 3,5-Cyclohexadiene-1,2-diol, 3-ethynyl-, (1S,2R)- (9CI)
• Synonyms: 3,5-Cyclohexadiene-1,2-diol, 3-ethynyl-, (1S,2R)- (9CI)
• CAS NO: 114763-29-0
• Molecular Formula: C₈H₈O₂
• Molecular Weight: 136.14792
• Mol File: 114763-29-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5-Cyclohexadiene-1,2-diol, 3-ethynyl-, (1S,2R)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Cyclohexadiene-1,2-diol, 3-ethynyl-, (1S,2R)- (9CI)(114763-29-0)
• EPA Substance Registry System: 3,5-Cyclohexadiene-1,2-diol, 3-ethynyl-, (1S,2R)- (9CI)(114763-29-0)

Safety Data

• Hazardous Substances Data: 114763-29-0(Hazardous Substances Data)

Upstream product

• 138769-92-3 cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene 
• 67451-62-1 cis-(1S,2S)-1,2-dihydroxy-3-bromocyclohexa-3,5-diene 
• 108-86-1 bromobenzene 
• 591-50-4 iodobenzene 
• 536-74-3 phenylacetylene 
• 138769-95-6 (1S,2R)-3-Trimethylsilanylethynyl-cyclohexa-3,5-diene-1,2-diol 
• 994-89-8 tributylethynyltin 

Downstream Products

• 209858-52-6 (1S,7S,10R,11S)-1-Ethynyl-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 

Relevant articles and documents

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.

Enzymatic and chemoenzymatic synthesis and stereochemical assignment of cis-dihydrodiol derivatives of monosubstituted benzenes

Toluene dioxygenase-catalysed oxidation of mono-substituted benzene substrates (R = F, Cl, Br, I, Me, Et, CH2OAc, CH=CH2, C=CH, CF3, CN, OMe, OEt, SMe) in growing cultures of Pseudomonas putida UV4 yielded the corresponding cis-dihydrodiol metabolites. Palladium-catalysed cross-coupling of cis-(1S,2S)-1,2-dihydroxy-3-iodocyclohexa-3,5-diene with a range of tributyltin compounds provided a chemoenzymatic route to a further series of cis-dihydrodiol derivatives of monosubstituted benzenes (R = D, CH2CH=CH2, Bun, SEt, SPr1, SBu1, SPh, SC6H4Me-4). The enantiopurities and absolute configurations of the cis-dihydrodiols, obtained by both enzymatic and chemoenzymatic routes, were determined by several new methods including 1H NMR spectroscopic analysis of the bis-MTPA esters of the 4-phenyl-1,2,4-triazoline-3,5-dione cycloadducts, X-ray crystallography, circular dichroism spectroscopy and stereochemical correlation.

Enzymatic and Chemical Syntheses of cis-Dihydrodiol Derivatives of Monocyclic Arenes

Metabolism of bromobenzene and iodobenzene by growing cultures of Pseudomonas putida UV4 gave the corresponding cis-dihydrodiol products 1 and 2 in high yields; subsequent direct chemical substitution of the halogen atoms in these metabolites provided a new range of enantiomerically pure cis-dihydrodiols of known absolute configuration.