7,8-dihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene | 37994-80-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 7,8-dihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene
• 英文别名: trans-7,8,9,10-Tetrahydrobenzo(a)pyrene-7,8-diol；(7S,8S)-7,8,9,10-tetrahydrobenzo[a]pyrene-7,8-diol
• CAS: 37994-80-2
• 化学式: C₂₀H₁₆O₂
• 分子量: 288.346
• InChiKey: BZKFNBASVGRQMC-PXNSSMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7,8-dihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene 在 二乙胺基三氟化硫 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 7-氟苯并(a)芘
  参考文献：
  名称：

  A novel synthesis of 7-fluorobenzo[a]pyrene involving two new molecular rearrangements

  摘要：

  DOI：

  10.1021/ja00516a068
• 作为产物：
  描述：

  苯并(a)芘-7,8-二酮 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 16.0h， 以42%的产率得到7,8-dihydroxy-7,8,9,10-tetrahydrobenzo[a]pyrene
  参考文献：
  名称：

  Synthesis of the non-K-region o-quinones and dihydrodiols of polycyclic aromatic hydrocarbons from the corresponding phenols

  摘要：

  DOI：

  10.1021/jo01310a029

文献信息

• Enantioselective synthesis of the tumorigenic anti-diol epoxide metabolites of benzo[a]pyrene
  作者：Ronald G. Harvey、Xiao-Qing Tang

  DOI：10.1016/0040-4039(95)00385-p

  日期：1995.4

  Efficient, highly enantioselective syntheses of (+) and (−)-anti-benzo[a]pyrene diol epoxide (BPDE) from 9,10-dihydrobenzo[a]pyrene are described. Initial epoxidation catalyzed by (salen) Mn(III) complex gives 7,8-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (>90% ee). Acid-catalyzed hydration occurs regio- and stereo-selectively to furnish the trans-tetrahydrodiols which are converted into the optically

  描述了由9,10-二氢苯并[a] py制成的高效，高对映选择性的（+）和（-）-抗-苯并[a] py二醇环氧化物（BPDE）。（salen）Mn（III）配合物催化的初始环氧化反应得到7,8-环氧-7,8,9,10-四氢苯并[a] py（> 90％ee）。酸催化的水合在区域和立体选择性地发生，以提供反式-四氢二醇，该反式-四氢二醇被转化为光学活性的抗-BPDE。
• Enantioselective synthesis of the (+)-anti-7,8-dihydrodiol-9,10-epoxide of the potent carcinogen benzo[a]pyrene
  作者：Xiaoming Huang、Thomas M. Harris

  DOI：10.1039/c39950001699

  日期：——

  The title compound, the most important genotoxic metabolite of benzo[a]pyrene, has been prepared efficiently in a synthesis which capitalized on Jacobsen-type enantioselective epoxidation of 9,10-dihydrobenzo[a]pyrene, cleavage of the epoxide by KOH–Me2SO to give the tetrahydro-trans-7,8-diol, and formation of the dibenzoate from which the contaminating antipode was removed by crystallization.

  利用 9,10- 二氢苯并[a]芘的雅各布森型对映体选择性环氧化作用、环氧化物在 KOH-Me2SO 作用下裂解生成四氢-反式-7,8-二醇，并形成二苯甲酸酯，通过结晶去除其中的污染性反式，从而高效地制备出了苯并[a]芘最重要的基因毒性代谢物--标题化合物。
• (+)- and (–)-Benzo[a]pyrene 7,8-oxide : synthesis, absolute stereochemistry, and stereochemical correlation with other mammalian metabolites of benzo[a]pyrene
  作者：Derek R. Boyd、Guru S. Gadaginamath、Anil Kher、John F. Malone、Haruhiko Yagi、Donald M. Jerina

  DOI：10.1039/p19800002112

  日期：——

  Optically pure samples of (+)- and (–)-benzo[a]pyrene 7,8-oxide have been synthesized from the separated diastereoisomers of trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tetrahydrobenzo[a]pyrene. The latter separation was effected by short-column chromatography–recrystallization or high pressure liquid chromatography. The absolute stereochemistry of (+)-trans-8-bromo-7-menthyloxyacetoxy-7,8,9,10-tet

  从分离的反式-8-溴-7-薄荷氧基乙酰氧基-7,8,9,10-四氢苯并的非对映异构体合成了（+）-和（-）-苯并[ a ] re7,8-氧化物的光学纯样品[ a ]。后者的分离是通过短柱色谱-重结晶或高压液相色谱进行的。通过X射线晶体结构分析，将（+）-反式-8-溴-7-薄荷氧基乙酰氧基-7,8,9,10-四氢苯并[ a ] py的绝对立体化学定为（7 S，8 S）。; 反过来，这种结构已经明确地与（7 S，8 R）-（-）-苯并[ a ] py 7,8-氧化物和一系列哺乳动物代谢产物。
• Superoxide oxidation: a novel route to aromatic 1,2-dicarboxylic acids
  作者：Chariklia Sotiriou、Wenni Lee、Roger W. Giese

  DOI：10.1021/jo00294a033

  日期：1990.3
• Resolution of polycyclic aromatic hydrocarbon dihydrodiols via diastereomeric formaldehyde acetals
  作者：Mahesh K. Lakshman、Surendrakumar Chaturvedi、Panna L. Kole、James H. Windels、Mark B. Myers、Michael A. Brown

  DOI：10.1016/s0957-4166(97)00464-3

  日期：1997.10

  Diastereomeric formaldehyde acetals, formed from the reaction of racemic benzo[a]pyrene dihydrodiol and (-)-chloromethylmenthyl ether, are novel intermediates for effecting the convenient resolution of these metabolites by HPLC. This resolution technique seems generally applicable since the dihydrodiols of benzo[c]phenanthrene can also be readily resolved through this methodology. Key differences in the proton NMR spectra of the diastereomeric dihydrodiol menthyloxymethyl ethers have been identified which could be used for absolute stereochemical assignments. (C) 1997 Elsevier Science Ltd.