3-Hydroxy-15,16-dihydrocyclopentaphenanthrene | 97835-10-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-Hydroxy-15,16-dihydrocyclopentaphenanthrene
• 英文别名: 16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol
• CAS: 97835-10-4
• 化学式: C₁₇H₁₄O
• 分子量: 234.298
• InChiKey: ZYSROUYANXUFML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-15,16-dihydrocyclopentaphenanthrene 在 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 adogen 464 、 potassium nitrososulfonate 、 氧气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 水 、 苯 为溶剂， 反应 78.25h， 生成 trans-3,4-Dihydroxy-anti-1,2-epoxy-1,2,3,4,15,16-hexahydrocyclopentaphenanthrene
  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
• 作为产物：
  描述：

  16,17-dihydro-3-methoxy-15H-cyclopentaphenanthren-17-one 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以88%的产率得到3-Hydroxy-15,16-dihydrocyclopentaphenanthrene
  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

文献信息

• Synthesis of the active dihydrodiol and diol epoxide metabolites of the steroid-related carcinogen 15,16-dihydrocyclopenta[a]phenanthrene and its 11-methyl derivative
  作者：Robert J. Young、Cecilia Cortez、Ernestina Luna、Hongmee Lee、Ronald G. Harvey

  DOI：10.1021/jo00054a017

  日期：1993.1

  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.