1,2-环氧-1H-环戊二烯并[a]菲-3,4-二酚,2,3,4,15,16,17-六氢-11-甲基-,(1a,2a,3a,4b)-(9CI) | 145679-85-2

• 中文名称: 1,2-环氧-1H-环戊二烯并[a]菲-3,4-二酚,2,3,4,15,16,17-六氢-11-甲基-,(1a,2a,3a,4b)-(9CI)
• 英文名称: trans-3,4-Dihydroxy-syn-1,2-epoxy-1,2,3,4,15,16-hexahydro-11-methylcyclopentaphenanthrene
• 英文别名: (3S,5R,6S,7R)-18-methyl-4-oxapentacyclo[9.7.0.02,8.03,5.012,16]octadeca-1(11),2(8),9,12(16),17-pentaene-6,7-diol
• CAS: 145679-85-2
• 化学式: C₁₈H₁₈O₃
• 分子量: 282.339
• InChiKey: DWZYLQQRBUCHIM-VSZNYVQBSA-N

物化性质

• 沸点：
  539.1±50.0 °C(Predicted)
• 密度：
  1.415±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-Bromo-1,2,3,4,15,16-hexahydro-11-methyl-1,3,4-trihydroxycyclopentaphenanthrene 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 0.67h， 以72%的产率得到1,2-环氧-1H-环戊二烯并[a]菲-3,4-二酚,2,3,4,15,16,17-六氢-11-甲基-,(1a,2a,3a,4b)-(9CI)
  参考文献：
  名称：

  Synthesis of the active dihydrodiol and diol epoxide metabolites of the steroid-related carcinogen 15,16-dihydrocyclopenta[a]phenanthrene and its 11-methyl derivative

  摘要：

  Cyclopenta[a]phenanthrenes are a class of environmentally occurring carcinogens that are structurally related to sterols. While the parent hydrocarbon is biologically inactive, its 11-methyl and 17-keto derivatives are relatively potent carcinogens. Recent research has identified trans-3,4-dihydrodiol metabolites as the metabolic precursors of the corresponding anti- and/or syn-diol epoxides, implicated as the ultimate carcinogenic forms that bind to DNA. We now report the synthesis of the trans-3,4-dihydrodiol derivatives of cyclcopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene, 3a and 3b, respectively, and the corresponding anti- and syn-diol epoxides of each of these hydrocarbons, 4a, 4b and 5a, 5b, respectively. Syntheses of the analogous trans-3,4-dihydrodiol metabolites of the 17-keto derivatives of cyclopenta[a]phenanthrene and 11-methylcyclopenta[a]phenanthrene are described in the accompanying paper.

  DOI：

  10.1021/jo00054a017