39834-45-2

Usage

Uses

An initial mammalian metabolite of Phenanthrene.

InChI:InChI=1/C14H10O/c1-2-4-11-9(3-1)5-6-10-7-8-12-14(15-12)13(10)11/h1-8,12,14H

Upstream product

• 85-01-8 phenanthrene 
• 354762-78-0 (-)-(3S,4S)-1-Bromo-3-acetoxy-4-chloro-1,2,3,4-tetrahydrophenanthrene 
• 56179-96-5 4-Acetoxy-1,3-dibrom-1,2,3,4-tetrahydrophenanthren 
• 56179-98-7 1,3-Dibrom-4-trifluoracetoxy-1,2,3,4-tetrahydrophenanthren 
• 56179-98-7 Trifluoro-acetic acid (3R,4R)-1,3-dibromo-1,2,3,4-tetrahydro-phenanthren-4-yl ester 
• 56179-85-2 trans-3-bromo-4-hydroxy-1,2,3,4-terahydrophenanthrene 
• 39834-45-2 Phenanthren-3,4-oxid 
• 39834-45-2 (+)-(3S,4R)-3,4-epoxy-3,4-dihydrophenanthrene 
• 78549-60-7 (-)-3-bromo-4-trifluoroacetoxy-1,2,3,4-tetrahydrophenanthrene 
• 78549-54-9 (-)-(3R,4R)-trans-3-bromo-4-hydroxy-1,2,3,4-tetrahydrophenanthrene 
• 313511-71-6 3-bromo-1,2,3,4-tetrahydro-4-hydroxyphenanthrene 
• 80522-77-6 (-)-(3R,4R)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-1,2,3,4-tetrahydrophenanthrene 
• 80522-83-4 (+)-(3S,4S)-trans-3-bromo-4-(2-methoxy-2-phenyl-2-trifluoromethylacetoxy)-1,2,3,4-tetrahydrophenanthrene 
• 354762-74-6 (-)-(3S,4S)-3-Acetoxy-4-chloro-1,2,3,4-tetrahydrophenanthrene 

Downstream Products

• 39834-45-2 phenanthrene 3,4-oxide 

Relevant academic research and scientific papers

Synthesis and isomerization of arene oxide metabolites of phenanthrene, triphenylene, dibenz[a,c]anthracene and dibenz[a,h]anthracene

Dibenz[a,h]anthracene 3,4-oxide 5ARS, synthesised from the enantiopure dibromoMTPA precursor 9ARRS*, was found to have totally racemized and to be accompanied by benz[5,6]anthra[1,2-b]oxepine 11A. Phenanthrene 3,4-oxide 5BRS/su

A General Method for the Resolution of Cyclic trans-Bromohydrin Enantiomers. Absolute Configuration by Crystal Structure Analysis of a 2-Methoxy-2-phenyl-2-trifluoromethylacetate (MTPA) Diastereoisomer

trans-Bromohydrins of 1,2,3,4-tetrahydronaphthalene (1a), 1,2,3,4-tetrahydroanthracene (1b), and 1,2,3,4-tetrahydrophenanthrene (1c) and (1d) were isolated in optically pure forms by reductive cleavage of the corresponding 2-methoxy-2-phenyl-2-trifluoromethylacetate (MTPA) diastereoisomers (2a-d) which had been separated by preparative h.p.l.c.Using reactions with established mechanisms and stereochemistry, the configurations at the chiral centres in the bromohydrins (1) were correlated with those in the tetrahydroepoxides (5), the arene oxides (7), and cis- (3) and trans- (4) tetrahydrodiols.An X-ray structure analysis of the 1,2,3,4-tetrahydroanthracene bromo-MTPA ester (+)-(2bE) indicated the trans equatorial quasi-equatorial conformation and confirmed the absolute stereochemistry of the MTPA group as (S).

Racemization of Phenanthrene 3,4-Oxide. Absolute Stereochemistry of cis- and trans-Phenanthrene 3,4-Dihydrodiols

trans-3,4-Dihydroxy-1,2,3,4-tetrahydrophenanthrene (11) and cis-3,4-dihydroxy-1,2,3,4-tetrahydrophenanthrene (12) have been prepared in optically pure form via: (i) chromatographic separation of the trans-3-bromo-4-menthyloxyacetoxy-1,2,3,4-tetrahydrophenanthrene diastereoisomers (7a), (7b), (ii) conversion of (7a) into the optically pure (+)-tetrahydro-3,4-epoxide (8), (iii) acid-catalysed hydrolysis of (+)-(8) by attack at C-4 to yield (+)-trans-(11) and (-)-cis-(12).Several lines of evidence, including spectral methods and chemical transformation to compounds of known absolute stereochemistry, have been used to assing absolute stereochemistry to all chiral compounds described in the present study.The availability of optically pure diols (11) and (12) has allowed the absolute stereochemistry of the trans- and cis-3,4-dihydrodiol metabolites of phenanthrene (4) and (2) to be determined as (-)-(3R,4R) and (+)-(3S,4R) respectively.Phenanthrene 3,4-oxide,an initial mammalian metabolite of phenanthrene prepared from optically pure precursors, was optically active but racemized spontaneously at ambient temperature.

AN IMPROVED METHOD FOR THE SYNTHESIS OF OPTICALLY PURE EPOXIDE AND ALCOHOL DERIVATIVES OF CHIRAL BROMOHYDRINS

The resolution of arene oxides, diols and other derivatives of bromohydrins has been markedly improved by the use of bromohydrin esters of (-)-(S)-α-methoxy-α-trifluoromethyl-phenylacetic acid (MTPA).

Stereochemical and Mechanistic Aspects of Sulphoxide, Epoxide, Arene Oxide, and Phenol Formation by Photochemical Oxygen Atom Transfer from Aza-aromatic N-Oxides

Stereoselectivity and relative yields are determined for the sulphoxide formation resulting from the u.v. irradiation of a range of aza-aromatic N-oxides in the presence of cyclic thioethers.A comparison is made with the results of oxidation by oxaziridines and by mono-oxygenase enzymes present in the fungus Aspergillus niger.The photochemical oxidation results are consistent with a transition state involving an oxaziridine intermediate where partial bonding of the oxygen atom to the ring nitrogen atom is maintained during the oxygen transfer process.Photolysis of aza-aromatic N-oxides in the presence of cis- and trans-olefins yields epoxides. cis-4-Methylpent-2-ene yielded both cis and trans-epoxides in almost equal proportions indicating that the oxygen atom addition to a carbon-carbon bond in this system is non-concerted.The photochemically induced oxygenation of perdeuteriated aromatic substrates provides no evidence for direct insertion of an oxygen atom into an aromatic carbon-hydrogen bond.Addition of an oxygen atom to form an epoxide (arene oxide) intermediate in this system is evidenced by the NIH shift in a wide range of aromatic substrates, and by the detection of arene oxide intermediates (and their isomeric phenols) from naphthalene and phenanthrene.