11-甲氧基-15,16-二氢-17H-环戊二烯并[a]菲-17-酮 | 5836-85-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 中文名称: 11-甲氧基-15,16-二氢-17H-环戊二烯并[a]菲-17-酮
• 英文名称: 11-methoxycyclopenta[a]phenanthren-17-one
• 英文别名: 15,16-dihydro-11-methoxycyclopentaphenanthren-17-one；11-Methoxy-15,16-dihydro-cyclopentaphenanthren-17-on；11-methoxy-15,16-dihydro-cyclopenta[a]phenanthren-17-one；11-Methoxy-15,16-dihydro-cyclopenta[a]phenanthren-17-on；11-Methoxy-15,16-dihydrocyclopenta(a)phenanthren-17-one；11-methoxy-15,16-dihydrocyclopenta[a]phenanthren-17-one
• CAS: 5836-85-1
• 化学式: C₁₈H₁₄O₂
• 分子量: 262.308
• InChiKey: NGXQHSGMHCOILD-UHFFFAOYSA-N

物化性质

• 沸点：
  365.55°C (rough estimate)
• 密度：
  1.1113 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

上下游信息

反应信息

• 作为反应物：
  描述：

  11-甲氧基-15,16-二氢-17H-环戊二烯并[a]菲-17-酮 在 溴 、 potassium acetate 作用下， 以 氯仿 为溶剂， 反应 68.0h， 生成 Acetic acid 11-methoxy-17-oxo-16,17-dihydro-15H-cyclopenta[a]phenanthren-16-yl ester
  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 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 120.0h， 生成 11-甲氧基-15,16-二氢-17H-环戊二烯并[a]菲-17-酮
  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 (1,2-cyclopentenophenanthrenes). Part II. Derivatives containing further unsaturation in ring D
  作者：M. M. Coombs

  DOI：10.1039/j39660000963

  日期：——

  the Δ15– 17H-compound (A), but at 100° the Δ16– 15H-isomer was formed. Base-catalysed condensation of (A) with acetone and aryl aldehydes yielded 17-substituted-methylene derivatives. The chemical shifts of protones attached to ring D in these compounds are listed.

  通过格氏反应从相应的15,16-二氢-17-酮制备了取代的17-甲基-15 H-环戊[ a ]菲，并将其还原为Diels烃的类似物。通过Witting反应获得15，16-二氢-17-亚甲基衍生物（未取代）。消除从17甲苯p在170 -sulphonyloxy化合物°得到Δ 15 - 17 ħ -化合物（A），但在100℃的Δ 16 - 15 ħ形成异构体。（A）与丙酮和芳基醛的碱催化缩合产生17-取代的亚甲基衍生物。列出了这些化合物中连接在环D上的质子的化学位移。
• 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：——
• 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：——
• 72. Experiments on the synthesis of substances related to the sterols. Part XXIX
  作者：Robert Robinson、S. N. Slater

  DOI：10.1039/jr9410000376

  日期：——
• CYP1 induction, binding to the hepatic aromatic hydrocarbon receptor and mutagenicity of a series of 11-alkoxy cyclopenta[a]phenanthren-17-ones: a structure activity relationship
  作者：Gary W. Boyd、Maurice M. Coombs、Costas Ioannides

  DOI：10.1016/0300-483x(94)02870-z

  日期：1995.1

  A series of four 11-alkoxy cyclopenta[a]phenanthren-17-ones, ranging from the methoxy to the butoxy derivative, has been synthesised in order to investigate the effect of the size of the 11-substituent on the mutagenicity and ability of these compounds to induce hepatic CYP1 activity in rats. The latter was monitored by using as diagnostic probes methoxy and ethoxy-resorufin, and immunologically in Western blots employing anti-CYP1A1 antibodies. All four members of the series induced both CYP1A1 and CYP1A2 activities and apoprotein levels, but the methoxy- and ethoxy-CPP-17-ones were clearly the most potent. Of the four isomers, only 11-methoxy-CPP-17-one displaced H-3-TCDD from the cytosolic Ah receptor. Similarly only 11-methoxy-CPP-17-one elicited a positive mutagenic response in the Ames test in the presence of an Aroclor 1254-induced activation system. The relevance of these findings to the carcinogenicity of these compounds in the mouse skin painting model is discussed.