15,16-Dihydro-3-methoxy-11-methylcyclopentaphenanthrene | 145627-72-1

• 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-3-methoxy-11-methylcyclopentaphenanthrene
• 英文别名: 3-methoxy-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthrene
• CAS: 145627-72-1
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: RXTGJNNBBSXLLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

上下游信息

反应信息

• 作为反应物：
  描述：

  15,16-Dihydro-3-methoxy-11-methylcyclopentaphenanthrene 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 氢气 、 三溴化硼 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， -78.0~25.0 ℃ 、220.64 kPa 条件下， 反应 48.0h， 生成 Benzoic acid 17-hydroxy-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Synthesis of the trans-3,4-dihydrodiol metabolites of the steroid-related carcinogen 15,16-dihydrocyclopenta[a]phenanthren-17-one and its 11-methyl derivative

  摘要：

  Cyclopenta[a]phenanthrenes are a unique class of carcinogenic polycyclic aromatic hydrocarbons that are structurally related to steroids. Optimum tumorigenic activity is associated with a methyl group in the 11-position and a keto group in the 17-position. Syntheses of the putative active trans-3,4-dihydrodiol and anti- and syn-diol epoxide metabolites of cyclopenta[a]phenanthrene and its 11-methyl derivative are described in the preceding paper. This paper reports the syntheses of the analogous trans-3,4-dihydrodiol derivatives of these same hydrocarbons with a 17-carbonyl function. The related isomeric diol epoxide derivatives were found to be too unstable to isolate in pure state.

  DOI：

  10.1021/jo00054a018
• 作为产物：
  描述：

  2-<2-<1-(6-Methoxynaphthyl)>propyl>cyclopentanone 在 palladium on activated charcoal 甲烷磺酸 作用下， 生成 15,16-Dihydro-3-methoxy-11-methylcyclopentaphenanthrene
  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.
• Synthesis of the trans-3,4-dihydrodiol metabolites of the steroid-related carcinogen 15,16-dihydrocyclopenta[a]phenanthren-17-one and its 11-methyl derivative
  作者：Ronald G. Harvey、Robert J. Young、Cecilia Cortez、Hongmee Lee、Ernestina Luna

  DOI：10.1021/jo00054a018

  日期：1993.1

  Cyclopenta[a]phenanthrenes are a unique class of carcinogenic polycyclic aromatic hydrocarbons that are structurally related to steroids. Optimum tumorigenic activity is associated with a methyl group in the 11-position and a keto group in the 17-position. Syntheses of the putative active trans-3,4-dihydrodiol and anti- and syn-diol epoxide metabolites of cyclopenta[a]phenanthrene and its 11-methyl derivative are described in the preceding paper. This paper reports the syntheses of the analogous trans-3,4-dihydrodiol derivatives of these same hydrocarbons with a 17-carbonyl function. The related isomeric diol epoxide derivatives were found to be too unstable to isolate in pure state.