15131-84-7

Usage

InChI:InChI=1/C18H12O/c1-2-6-12-11(5-1)9-10-14-13-7-3-4-8-15(13)17-18(19-17)16(12)14/h1-10,17-18H

Upstream product

• 132335-14-9 2-Phenylnaphthalene-1,2'-dicarboxaldehyde 
• 218-01-9 chrysene 
• 74087-85-7 3,3-dimethyldioxirane 
• 89523-48-8 trans-5-acetoxy-6-bromo-5,6-dihydrochrysene 

Downstream Products

• 105882-38-0 (5S,6S)-5-Methoxy-5,6-dihydro-chrysen-6-ol 
• 105882-39-1 (5S,6S)-6-Methoxy-5,6-dihydro-chrysen-5-ol 
• 37515-51-8 6-hydroxychrysene 
• 84498-34-0 chrysen-5-ol 
• 7499-59-4 6-acetoxychrysene 
• 120018-42-0 6-Azidochrysene 
• 132335-15-0 1a,11c-Dihydrochryseno<5,6-b>azirine 
• 105882-39-1 (5S,6R)-6-Methoxy-5,6-dihydro-chrysen-5-ol 

Relevant academic research and scientific papers

Reactions of the K-Region Epoxides of Polycyclic Aromatic Hydrocarbons with Phosphodiesters. A Potential Detoxification Reaction

Phenanthrene 9,10-oxide reacts with diethyl hydrogen phosphate to give 9-phenanthrol.The reaction was first order in both epoxide and phosphate concentrations, with a pseudo-first-order rate constant kφ = 6.2e-1 mol-1Ls-1.Similarly, chrysene 5,6-oxide on reaction with phosphate opened regiospecifically to give 6-chrysenol.Several anilinium phosphate salts were prepared and reacted with phenanthrene 9,10-oxide.The extent of reaction was markedly influenced by the pKa of the anilinium salt.The biological implications of this study in understanding the relative noncarcinogenicity of K-region arene oxides are discussed.

The reaction of dimethyldioxirane with chrysene: Formation of a trioxide

Oxidation of chrysene with dimethyldioxirane gives a number of products including the interesting trioxide, chrysene-5,6:4b, 10b:11,12-trioxide, 3. The x-ray crystallographic structure of 3 indicates that it is a non-planar system.

Arene Imine Derivatives of Chrysene and of Benzochrysene: 1a,11c-Dihydrochrysenoazirine and 1a,13c-Dihydrobenzochrysenoazirine

The syntheses of the K-imines (which are also benzo-bay-region derivatives) of chrysene (1) and benzochrysene (2) are described.The preparation of 1a,11c-dihydrochrysenoazirine (5) was accomplished by treatment of 1a,11c-dihydrochrysenooxirene (4) with sodium azide, and the mixture of trans-azido-alcohols 6 and 7, so formed, was either cyclized with triethyl phosphite, or converted into E-6-azido-5-chloro-5,6-dihydrochrysene (8) followed by lithium aluminium hydride reduction.The synthesis of 1a,13c-dihydrobenzochrysenoazirine (12) included the transformation of the corresponding oxide 11 into a mixture of E-9-azido-9,10-dihydrobenzochrysen-10-ol (13) and E-10-azido-9,10-dihydrobenzochrysen-9-ol (14), and reaction with tri-n-butylphosphine to give a mixture of Staudinger adducts 15 and 16 that underwent thermal decomposition into 12 upon heating in boiling dichloromethane.

FACILE SYNTHESIS OF K-REGION ARENE OXIDES

Polycyclic aromatic hydrocarbons reacts at the K-region with N-bromoacetamide in acetic acid to provide trans-bromohydrin acetates which are readly cyclized to arene oxides.The simplicity of the approach makes radioactive and optically active K-region arene oxides easily available.