15,16-dihydro-11-hydroxycyclopenta[a]phenanthrene | 83053-63-8

• 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: 15,16-dihydro-11-hydroxycyclopenta[a]phenanthrene
• 英文别名: 11-hydroxy-15,16-dihydro-cyclopenta[a]phenanthren-17-one；11-Hydroxy-15,16-dihydro-cyclopenta[a]phenanthren-17-on；17H-Cyclopenta(a)phenanthren-17-one, 15,16-dihydro-11-hydroxy-；11-hydroxy-15,16-dihydrocyclopenta[a]phenanthren-17-one
• CAS: 83053-63-8
• 化学式: C₁₇H₁₂O₂
• 分子量: 248.281
• InChiKey: JCENDEWOZZOHKV-UHFFFAOYSA-N

物化性质

• 沸点：
  351.35°C (rough estimate)
• 密度：
  1.1290 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  15,16-dihydro-11-hydroxycyclopenta[a]phenanthrene 在 溴 、 potassium carbonate 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 120.0h， 生成 15-bromo-15,16-dihydro-11-methoxycyclopentaphenanthren-17-one
  参考文献：
  名称：

  Coombs, Maurice M; Boyd, Gary W., Journal of Chemical Research, Miniprint, 1998, # 11, p. 2901 - 2911

  摘要：

  DOI：
• 作为产物：
  描述：

  11-acetoxy-15,16-dihydrocyclopentaphenanthren-17-one 在 甲醇 、 氢氧化钾 作用下， 反应 48.0h， 以7.5 g的产率得到15,16-dihydro-11-hydroxycyclopenta[a]phenanthrene
  参考文献：
  名称：

  Coombs, Maurice M; Boyd, Gary W., Journal of Chemical Research, Miniprint, 1998, # 11, p. 2901 - 2911

  摘要：

  DOI：

文献信息

• Potentially carcinogenic cyclopenta[a]phenanthrenes. Part V. Synthesis of 15,16-dihydro-7-methylcyclopenta[a]phenanthren-17-one
  作者：M. M. Coombs、S. B. Jaitly

  DOI：10.1039/j39710000230

  日期：——

  15,16-Dihydro-7-methylcyclopenta[a]phenanthren-17-one has been prepared by sodium and liquid ammonia reduction of the diethyl phosphate of its readily available 11-hydroxy-derivative.

  15,16-二氢-7- methylcyclopenta [一个]菲-17-酮已准备由钠和其容易得到11-羟基衍生物的磷酸二乙酯的液态氨还原。
• 261. Experiments on the synthesis of substances related to the sterols. Part XXI. A new synthesis of derivatives of ketocyclopentenophenanthrene
  作者：Robert Robinson

  DOI：10.1039/jr9380001390

  日期：——
• 102. Experiments on the synthesis of substances related to the sterols. Part XXXVI (Continuation of part XXII)
  作者：A. Koebner、Robert Robinson

  DOI：10.1039/jr9410000566

  日期：——
• Bioactivation of the carcinogen 11-methoxy-16,17-dihydro-15H-cyclopenta[a]phenanthrene
  作者：Fenton S Catterall、Maurice M Coombs、Costas Ioannides、Kim Walton

  DOI：10.1016/s1383-5718(99)00215-6

  日期：2000.2

  The title compound is a more potent carcinogen than would be anticipated from its simple phenanthrene structure lacking further D-ring conjugation. In vitro it undergoes microsomal metabolism to yield as major metabolites its 15- and 17-alcohols and its 16,17-diol; other minor metabolites are also derived from attack at the 5-membered ring, but no evidence of aromatic oxidation is apparent. The title compound is a weak mutagen in the Ames' test with Salmonella typhimurium TA100, bur only with microsomal bio-activation. The 17-ol and 16,17-diol are inactive, with or without biological activation. By contrast the 15-alcohol, a rather reactive compound, is a strong mutagen both in the presence and absence of the bio-activation system. This, therefore, may be the proximate carcinogen, and its structural analogy to the naturally occurring hepato-carcinogen safrole is noted. (C) 2000 Elsevier Science B.V. All rights reserved.
• Elvidge, John A.; Jones, John R.; Russell, Jeremy C., Journal of the Chemical Society. Perkin transactions II, 1985, p. 563 - 566
  作者：Elvidge, John A.、Jones, John R.、Russell, Jeremy C.、Wiseman, Alan、Coombs, Maurice M.

  DOI：——

  日期：——