131101-27-4

Usage

Chemical Properties

clear brown solution

InChI:InChI=1/C6H7FO2/c7-4-2-1-3-5(8)6(4)9/h1-3,5-6,8-9H/t5-,6+/m0/s1

Upstream product

• 462-06-6 fluorobenzene 

Downstream Products

• 131065-64-0 (1S,7S,10S,11S)-1-Fluoro-10,11-dihydroxy-4-phenyl-2,4,6-triaza-tricyclo[5.2.2.0^2,6]undec-8-ene-3,5-dione 
• 89533-81-3 (4S,5S,6S)-4,5,6-trihydroxycyclohex-2-enone 
• 131043-58-8 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8S,9S)-7-fluoro-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 
• 131101-31-0 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,7S,8S,9S)-7-fluoro-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 
• 363-52-0 3-fluorocatechol 
• 372-20-3 3-fluorophenol 
• 367-12-4 2-fluorophenol 
• 133218-73-2 Acetic acid (1S,2S,6R)-2,6-diacetoxy-5-hydroxy-cyclohex-3-enyl ester 
• 133319-94-5 (+)-(1S,5S,6S)-1,5,6-triacetoxy-4-oxocyclohex-2-ene 
• 123354-99-4 meso-Conduritol D tetraacetate 
• 133319-96-7 (1S,2S,3R,4S)-1,2,3,4-tetra-O-acetylconduritol C 
• 133319-93-4 (1S,2R,3S,4S)-5-cyclohexene-1,2,3,4-tetrol 
• 133218-71-0 6-fluoroconduritol C m-chlorobenzoate 
• 133218-72-1 6-fluoroconduritol C 

Relevant academic research and scientific papers

Enhancement of whole cell dioxygenase biotransformations of haloarenes by toxic ionic liquids

Accessing chirally pure cis-diols from arenes using micro-organisms over-expressing toluene dioxygenase (TDO) is now well established, but the conversions remain low for the more toxic and volatile substrates. For such arenes, improved production has alre

A comparative study of the synthesis of 3-substituted catechols using an enzymatic and a chemoenzymatic method

A series of cis-dihydrodiol metabolites, available from the bacterial dioxygenase-catalysed oxidation of monosubstituted benzene substrates using Pseudomonas putida UV4 , have been converted to the corresponding catechols using both a heterogeneous catalyst (Pd/c) and a naphthalene cis-diol dehydrogenase enzyme present in whole cells of the recombinant strain Escherichia coli DH5α(pUC129: nar B). A comparative study of the merits of both routes to 3-substituted catechols has been carried out and the two methods have been found to be complementary. A similarity in mechanism for catechol formation under both enzymatic and chemoenzymatic conditions, involving regioselective oxidation of the hydroxyl group at C-1, has been found using deuterium labelled toluene cis-dihydrodiols. The potential, of combining a biocatalytic step (dioxygenase-catalysed cis-dihydroxylation) with a chemocatalytic step (Pd/C-catalysed dehydrogenation), into a one-pot route to catechols, from the parent substituted benzene substrates, has been realised.

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.

Enantioselective Bacterial Biotransformation Routes to cis-Diol Metabolites of Monosubstituted Benzenes, Naphthalene and Benzocycloalkenes of Either Absolute Configuration

Enzyme-catalysed kinetic resolution and asymmetric dihydroxylation routes to enantiopure cis-diol metabolites of arenes and benzocycloalkenes of either absolute configuration have been developed using appropriate strains of the bacterium Pseudomonas putida.