17-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol | 1053182-92-5

• 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: 17-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol
• 英文别名: 17-[tert-butyl(diphenyl)silyl]oxy-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol
• CAS: 1053182-92-5
• 化学式: C₃₄H₃₄O₂Si
• 分子量: 502.728
• InChiKey: YVHLTKKFXQDILA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.57
• 重原子数：
  37
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  17-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol 在 potassium dihydrogenphosphate 、 adogen 464 、 potassium nitrososulfonate 作用下， 以 苯 为溶剂， 反应 3.0h， 以82%的产率得到17-<(tert-Butyldiphenylsilyl)oxy>-15,16-dihydro-11-methylcyclopentaphenanthrene-3,4-dione
  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：

  3-Methoxy-11-methyl-6,7,15,16-tetrahydrocyclopentaphenanthrene 在 palladium on activated charcoal 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 氢氧化钾 、 sodium tetrahydroborate 、 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 为溶剂， 反应 40.0h， 生成 17-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-16,17-dihydro-15H-cyclopenta[a]phenanthren-3-ol
  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

文献信息

• 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.