66008-19-3

Basic information

• Product Name: (1S,2R)-3-ethylcyclohexa-3,5-diene-1,2-diol
• CAS NO: 66008-19-3
• Molecular Formula: C₈H₁₂O₂
• Molecular Weight: 140.1797
• Mol File: 66008-19-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 250.1°C at 760 mmHg
• Flash Point: 118.3°C
• Density: 1.143g/cm³
• Vapor Pressure: 0.00351mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: (1S,2R)-3-ethylcyclohexa-3,5-diene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2R)-3-ethylcyclohexa-3,5-diene-1,2-diol(66008-19-3)
• EPA Substance Registry System: (1S,2R)-3-ethylcyclohexa-3,5-diene-1,2-diol(66008-19-3)

Safety Data

• Hazardous Substances Data: 66008-19-3(Hazardous Substances Data)

Upstream product

• 100-41-4 ethylbenzene 

Downstream Products

• 131043-57-7 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7R,8R,9S)-7-ethyl-3,5-dioxo-4-phenyl-9-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester 
• 131101-30-9 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7R,8R,9S)-7-ethyl-3,5-dioxo-4-phenyl-9-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl ester 

Relevant articles and documents

Enantioselective toluene dioxygenase catalysed di- and tri-hydroxylation of monosubstituted benzenes

Asymmetric cis-dihydroxylation to yield diols 2A-2G and sequential benzylic monohydroxylation-cis-dihydroxylation to yield triols 4A-4G (trihydroxylation), occurred during biotransformation of a series of monosubstituted alkylbenzene substrates 1A-1G using toluene dioxygenase, a biocatalyst present in Pseudomonas putida UV4. Dioxygenase-catalysed cis-dihydroxylation of the R and S benzylic alcohol enantiomers 3B-3D, 3B′-3D′ gave the corresponding enantiopure triols 4B-4D, 4B′-4D′. Biotransformation of substrates 1J-1L yielded cis-diols 2J-2L and a minor triol metabolite 4A. Benzylic alcohols 3J-3L were postulated as unstable intermediates yielding triol 4A via benzaldehyde 5 and benzyl alcohol 3A intermediates, cis-Dihydroxylation of monosubstituted benzylic substrates containing bulky groups (1H, 1I) or 1,4-dialkyl-substituted benzene substrates (10A-10C) gave the corresponding cis-dihydrodiol metabolites (2H, 2I, 11A-11C) exclusively. The cis-diols 2A-2L, 11A-11C and triols 4A-4F, 4B′-4D′ were stereochemically assigned as single enantiomers of 1S,2R-configuration based on NMR and CD spectroscopy. The absolute configurations of the exocylic chiral centres in the triol bioproducts 4A-4F, 4B′-4D′ were established by stereochemical correlation and aromatisation/hydrogenation to yield the corresponding enantiopure phenolic benzylic alcohols having similar CD spectra.

Enantiomeric Excess and Absolute Configuration Determination of cis-Dihydrodiols from Bacterial Metabolism of Monocyclic Arenes

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