methyl 2-methoxy-4H-cyclopentaphenanthrene-6-butyrate | 169383-24-8

• 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: methyl 2-methoxy-4H-cyclopentaphenanthrene-6-butyrate
• 英文别名: Methyl 4-(10-methoxy-3-tetracyclo[10.2.1.05,14.08,13]pentadeca-1(14),2,4,6,8,10,12-heptaenyl)butanoate
• CAS: 169383-24-8
• 化学式: C₂₁H₂₀O₃
• 分子量: 320.388
• InChiKey: HMWOVMOSRMDJFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-methoxy-4H-cyclopentaphenanthrene-6-butyrate 在 氢氧化钾 、 氢氟酸 作用下， 以 乙醇 为溶剂， 反应 25.0h， 生成 2-methoxy-6,7,8,9-tetrahydro-4H-cyclopentachrysen-9-one
  参考文献：
  名称：

  Stereoselective synthesis of putative diol epoxide metabolites of 4H-cyclopenta[def]chrysene.

  摘要：

  Syntheses of the anti-diol epoxide derivatives of the methylene-bridged polycyclic aromatic hydrocarbon 4H-cyclopenta[def]chrysene in both the bridge- and non-bridge-substituted rings (2 and 3) and the syn-diol epoxide derivative in the non-bridge-substituted ring (14) are described. These compounds are suspected to be active carcinogenic metabolites of the parent hydrocarbon. They are the first examples of the diol epoxide derivatives of a nonalternant methylene-bridged tumorigenic hydrocarbon to be synthesized, The bridge-substituted anti-diol epoxide derivative 2 is relatively stable, despite its relatively strained structure, and it possesses a unique ''locked'' structure which severely restricts conformational interconversion.

  DOI：

  10.1021/jo00120a039
• 作为产物：
  描述：

  8,9-dihydro-2-methoxy-4H-cyclopenta-(6-phenanthrylcarbonyl)propanoic acid 在 palladium on activated charcoal 氢氧化钾 、 对甲苯磺酸 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 54.0h， 生成 methyl 2-methoxy-4H-cyclopentaphenanthrene-6-butyrate
  参考文献：
  名称：

  Stereoselective synthesis of putative diol epoxide metabolites of 4H-cyclopenta[def]chrysene.

  摘要：

  Syntheses of the anti-diol epoxide derivatives of the methylene-bridged polycyclic aromatic hydrocarbon 4H-cyclopenta[def]chrysene in both the bridge- and non-bridge-substituted rings (2 and 3) and the syn-diol epoxide derivative in the non-bridge-substituted ring (14) are described. These compounds are suspected to be active carcinogenic metabolites of the parent hydrocarbon. They are the first examples of the diol epoxide derivatives of a nonalternant methylene-bridged tumorigenic hydrocarbon to be synthesized, The bridge-substituted anti-diol epoxide derivative 2 is relatively stable, despite its relatively strained structure, and it possesses a unique ''locked'' structure which severely restricts conformational interconversion.

  DOI：

  10.1021/jo00120a039