4-(4-Benzyloxy-phenyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 4-(4-Benzyloxy-phenyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine
• 英文别名: 4-(4-phenylmethoxyphenyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine
• 化学式: C₁₉H₁₉N₃O
• 分子量: 305.379
• InChiKey: IPORPIQXJQGXGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  49.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(4-Benzyloxy-phenyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine 在 溴 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 5-(5-bromomethyl-4,5-dihydro-1,3-thiazol-2-yl)-4-(4-benzyloxyphenyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine hydrotribromide
  参考文献：
  名称：

  Cyclization of thioureas from the series of 4-aryl(hetaryl)spinaceamines

  摘要：

  Reaction of allylthiocarbamoyl fragment of N-allylthioureas with excess bromine or iodine leads to the formation of 5-halomethyldihydrothiazole ring as confirms the dehydroiodination of the 5-(5-iodomethyl-4,5-dihydro-1,3-thiazol-2-yl)-4-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine with the formation of a 5-methylthiazole ring. The reaction of allylthiourea with hydrochloric acid affords a 5-methyldihydrothiazole ring.

  DOI：

  10.1134/s1070428014110189
• 作为产物：
  描述：

  4-苄氧基苯甲醛 、 histamine dichloride 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以71%的产率得到4-(4-Benzyloxy-phenyl)-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  摘要：

  4-Phenyl derivatives of spinaceamine and spinacine undergo mild catalytic hydrogenation under atmospheric pressure with cleavage of the C-4-N-5 bond to give 5-benzyl-substituted histamines and histidines. The process is likely to be facilitated by the double benzylic effect on the C-N bond of the imidazole and benzene rings.

  DOI：

  10.1023/a:1012346021943

文献信息

• Dehydrogenation of 4-phenyl-substituted spinaceamine and spinacine
  作者：N. N. Smolyar、M. G. Abramyants、Yu. M. Yutilov

  DOI：10.1134/s1070428006040099

  日期：2006.4

  The dehydrogenation of 4-phenyl-substituted spinaceamine and spinacine with elemental sulfur in dimethylformamide at 120-150 degrees C leads to the corresponding imidazo[4,5-c]pyridines. Sulfur may be regarded as a specific reagent for oxidative decarboxylation which accompanies dehydrogenation of 4-phenyl-substituted spinacine derivatives.
• Cyclization of thioureas from the series of 4-aryl(hetaryl)spinaceamines
  作者：N. V. Astashkina、D. A. Lomov、M. G. Abramyants、N. I. Korotkikh、N. N. Smolyar

  DOI：10.1134/s1070428014110189

  日期：2014.11

  Reaction of allylthiocarbamoyl fragment of N-allylthioureas with excess bromine or iodine leads to the formation of 5-halomethyldihydrothiazole ring as confirms the dehydroiodination of the 5-(5-iodomethyl-4,5-dihydro-1,3-thiazol-2-yl)-4-phenyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine with the formation of a 5-methylthiazole ring. The reaction of allylthiourea with hydrochloric acid affords a 5-methyldihydrothiazole ring.
• ——
  作者：Yu. M. Yutilov、M. G. Abramyants、N. N. Smolyar

  DOI：10.1023/a:1012346021943

  日期：——

  4-Phenyl derivatives of spinaceamine and spinacine undergo mild catalytic hydrogenation under atmospheric pressure with cleavage of the C-4-N-5 bond to give 5-benzyl-substituted histamines and histidines. The process is likely to be facilitated by the double benzylic effect on the C-N bond of the imidazole and benzene rings.