3,6-Dimethyl-9-(p-tolyl)-10(5-phenyltetrazol-1-yl)phenanthrene | 133387-53-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3,6-Dimethyl-9-(p-tolyl)-10(5-phenyltetrazol-1-yl)phenanthrene
• 英文别名: 1-[3,6-dimethyl-10-(4-methylphenyl)phenanthren-9-yl]-5-phenyltetrazole
• CAS: 133387-53-8
• 化学式: C₃₀H₂₄N₄
• 分子量: 440.547
• InChiKey: XDUFQVHWYKMNOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  34
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,6-Dimethyl-9-(p-tolyl)-10(5-phenyltetrazol-1-yl)phenanthrene 以 甲醇 为溶剂， 反应 24.0h， 以43%的产率得到7,9-Dimethyl-3a-(p-tolyl)-2-phenyl-3aH-phenanthro<9,10-d>imidazole
  参考文献：
  名称：

  Synthesis and properties of 4H-imidazoles. Part 2.

  摘要：

  The 1-(2,2-disubstituted alk-1-enyl)-5-phenyltetrazoles 2 and 4 are prepared from 1-methyl-5-phenyltetrazole and 5-phenyl-1-trimethylsilylmethyltetrazole by formation and appropriate interception of the alpha-lithioalkyl derivatives. Photolysis of the tetrazoles 2a and 4 gives the stable 4H-imidazoles 9 and 5, respectively. Similar photolysis of the tetrazole 2b gives the tetrazolophenanthrene 12 by an oxidative photocyclisation which is faster than nitrogen extrusion from the tetrazole ring. However, on further irradiation the tetrazolophenanthrene 12 can be transformed into the polycyclic 4H-imidazole 13. The 4H-imidazoles all undergo [1,5] alkyl or aryl shifts to carbon when heated, 5, 7, 9 and 13 giving 6, 8, 10 and 14 respectively.

  DOI：

  10.1039/p19910000335
• 作为产物：
  描述：

  1,1,2-Tris(p-tolyl)-2-(5-phenyltetrazol-1-yl)-ethene 在 air 、 碘 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 反应 1.0h， 以97%的产率得到3,6-Dimethyl-9-(p-tolyl)-10(5-phenyltetrazol-1-yl)phenanthrene
  参考文献：
  名称：

  Synthesis and properties of 4H-imidazoles. Part 2.

  摘要：

  The 1-(2,2-disubstituted alk-1-enyl)-5-phenyltetrazoles 2 and 4 are prepared from 1-methyl-5-phenyltetrazole and 5-phenyl-1-trimethylsilylmethyltetrazole by formation and appropriate interception of the alpha-lithioalkyl derivatives. Photolysis of the tetrazoles 2a and 4 gives the stable 4H-imidazoles 9 and 5, respectively. Similar photolysis of the tetrazole 2b gives the tetrazolophenanthrene 12 by an oxidative photocyclisation which is faster than nitrogen extrusion from the tetrazole ring. However, on further irradiation the tetrazolophenanthrene 12 can be transformed into the polycyclic 4H-imidazole 13. The 4H-imidazoles all undergo [1,5] alkyl or aryl shifts to carbon when heated, 5, 7, 9 and 13 giving 6, 8, 10 and 14 respectively.

  DOI：

  10.1039/p19910000335