3a-methyl-2-phenyl-4,5,6,7-tetrahydro-3aH-benzimidazole | 89002-64-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3a-methyl-2-phenyl-4,5,6,7-tetrahydro-3aH-benzimidazole
• 英文别名: 3a-methyl-2-phenyl-4,5,6,7-tetrahydrobenzimidazole
• CAS: 89002-64-2
• 化学式: C₁₄H₁₆N₂
• 分子量: 212.294
• InChiKey: CFCHARDAYQAMFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3a-methyl-2-phenyl-4,5,6,7-tetrahydro-3aH-benzimidazole 以22%的产率得到9-Methyl-2-phenyl-1,3-diazaspiro<4.4>nona-2,9-diene
  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-(2-methylcyclohex-1-enyl)-5-phenyltetrazole 以 Petroleum ether 为溶剂， 以55%的产率得到3a-methyl-2-phenyl-4,5,6,7-tetrahydro-3aH-benzimidazole
  参考文献：
  名称：

  Synthesis and properties of 4H-imidazoles

  摘要：

  烯基四唑（1）的光解为获得简单的 4H-imidazoles （2）提供了第一条合理的途径；当 C-5 处未被取代时，它们对亲核物具有很高的反应活性，并在加热时迅速重排为芳香族 1H-imidazoles。

  DOI：

  10.1039/c39830001082

文献信息

• Casey, Michael; Moody, Christopher; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1987, p. 1389 - 1394
  作者：Casey, Michael、Moody, Christopher、Rees, Charles W.

  DOI：——

  日期：——
• CASEY, MICHAEL;MOODY, CHRISTOPHER J.;REES, CHARLES W., J. CHEM. SOC. PERKIN TRANS.,(1987) N 6, 1389-1393
  作者：CASEY, MICHAEL、MOODY, CHRISTOPHER J.、REES, CHARLES W.

  DOI：——

  日期：——
• Synthesis and properties of 4H-imidazoles. Part 2.
  作者：Christopher J. Moody、Charles W. Rees、Richard G. Young

  DOI：10.1039/p19910000335

  日期：——

  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.
• Synthesis and properties of 4H-imidazoles
  作者：Michael Casey、Christopher J. Moody、Charles W. Rees

  DOI：10.1039/c39830001082

  日期：——

  Photolysis of alkenyltetrazoles (1) provides the first rational route to simple 4H-imidazoles (2); When unsubstituted at C-5 these are highly reactive towards nucleophiles and rearrange rapidly to the aromatic 1H-imidazoles on heating.

  烯基四唑（1）的光解为获得简单的 4H-imidazoles （2）提供了第一条合理的途径；当 C-5 处未被取代时，它们对亲核物具有很高的反应活性，并在加热时迅速重排为芳香族 1H-imidazoles。