一种新型氟化苯并[a]芘的合成：4,5-二氟苯并[a]芘。
Synthesis of a novel fluorinated benzo[a]pyrene: 4,5-difluorobenzo[a]pyrene.
作者信息
Agarwal S C, Lambert G, Padgett W, Nesnow S
机构信息
Environmental Health Research and Testing, Inc., Research Triangle Park, NC 27709.
出版信息
Carcinogenesis. 1991 Sep;12(9):1647-50. doi: 10.1093/carcin/12.9.1647.
The synthesis of 4,5-difluorobenzo[a]pyrene, as a fluorinated probe to investigate the involvement of the K-region in the further metabolic activation of benzo[a]pyrene metabolites, is described. Benzo[a]pyrene-4,5-dione obtained from 2,3-dichloro-5,6-dicyano-1,4-benzoquinone oxidation of cis-4,5-dihydro-4,5-dihydroxybenzo[a]pyrene was fluorinated with dimethylaminosulfur trifluoride to give 4H,5H,4,4,5,5,-tetra-fluorobenzo[a]pyrene. Defluorination using lithium aluminum hydride in tetrahydrofuran gave 4,5,-difluorobenzo[a]pyrene.
本文描述了4,5-二氟苯并[a]芘的合成，该化合物作为一种氟化探针，用于研究K区域在苯并[a]芘代谢物进一步代谢活化中的作用。由顺式-4,5-二氢-4,5-二羟基苯并[a]芘经2,3-二氯-5,6-二氰基-1,4-苯醌氧化得到的苯并[a]芘-4,5-二酮，用三氟甲磺酸二甲胺基硫进行氟化反应，得到4H,5H,4,4,5,5-六氟苯并[a]芘。在四氢呋喃中用氢化铝锂进行脱氟反应，得到4,5-二氟苯并[a]芘。
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