2-[2-(pyridin-4-yl)ethyl]-1H-benzimidazole | 149208-16-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-[2-(pyridin-4-yl)ethyl]-1H-benzimidazole
• 英文别名: 2-(2-pyridin-4-ylethyl)-1H-benzimidazole
• CAS: 149208-16-2
• 化学式: C₁₄H₁₃N₃
• mdl: MFCD25660036
• 分子量: 223.277
• InChiKey: VITMUOYKXATDJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-methoxy-N-methyl-3-pyridin-4-ylpropionamide 、 邻苯二胺 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以78%的产率得到2-[2-(pyridin-4-yl)ethyl]-1H-benzimidazole
  参考文献：
  名称：

  Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles

  摘要：

  One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.075

文献信息

• Weinreb amide as an efficient reagent in the one pot synthesis of benzimidazoles and benzothiazoles
  作者：Yadaganahalli K. Bommegowda、Gejjalagere S. Lingaraju、Saji Thamas、Koravangala S. Vinay Kumar、Challanayakanahally S. Pradeepa Kumara、Kanchugarakoppal S. Rangappa、Marilinganadoddi P. Sadashiva

  DOI：10.1016/j.tetlet.2013.03.075

  日期：2013.5

  One pot synthesis of 2-substituted benzimidazoles/benzothiazoles through condensation is followed by cyclization of Weinreb amide with o-diaminoarene or o-aminothiophenol is reported. In the presence of boron trifluoride etherate in 1,4-dioxane solvent, a high yield (75-94%) was achieved within 60 min. Weinreb amide shows high selectivity in the reaction, even in presence of other active functional groups such as carboxyl, halogen, cyano, and methoxy. (c) 2013 Elsevier Ltd. All rights reserved.