4H-cyclopentachrysen-2-ol | 160086-41-9

• 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: 4H-cyclopentachrysen-2-ol
• 英文别名: Pentacyclo[14.2.1.03,8.09,18.012,17]nonadeca-1,3,5,7,9(18),10,12,14,16-nonaen-14-ol
• CAS: 160086-41-9
• 化学式: C₁₉H₁₂O
• 分子量: 256.304
• InChiKey: XNDWYNOSROINLN-UHFFFAOYSA-N

物化性质

• 沸点：
  543.062±29.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.394±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4H-cyclopentachrysen-2-ol 在 sodium tetrahydroborate 、 potassium dihydrogenphosphate 、 adogen 464 、 potassium nitrososulfonate 、 氧气 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 49.5h， 生成 trans-1,2-dihydroxy-anti-3,3a-epoxy-1,2,3,3a-tetrahydro-4H-cyclopentachrysene
  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 、 sodium tetrahydroborate 、 氢氟酸 、 三溴化硼 、 对甲苯磺酸 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 二乙二醇 为溶剂， 反应 86.0h， 生成 4H-cyclopentachrysen-2-ol
  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

文献信息

• Stereoselective synthesis of putative diol epoxide metabolites of 4H-cyclopenta[def]chrysene.
  作者：Wei Dai、Elias Abu-Shqara、Ronald G. Harvey

  DOI：10.1021/jo00120a039

  日期：1995.7

  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.