2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrobromide | 109114-01-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrobromide
• CAS: 109114-01-4
• 化学式: BrH*C₈H₇F₃N₂O
• 分子量: 285.064
• InChiKey: IWPQLMLEFHUGSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  35.83
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 3-溴-1,1,1-三氟丙酮 以 丙酮 为溶剂， 以90%的产率得到2-(trifluoromethyl)-2,3-dihydroimidazo[1,2-a]pyridin-2-ol hydrobromide
  参考文献：
  名称：

  Intramolecular hydrogen bond stabilization of hemiaminal structures, precursors of imidazo[1,2-a]pyridine

  摘要：

  A theoretical study supported by calculations at the B3LYP/6-31+G and B3LYP/6-311++G(d,p) levels demonstrated that an attractive interaction involving a hydrogen bond between a hydroxyl group and an acceptor halogen atom (O-H center dot center dot center dot Cl) is present in 2,3-dihydro-2-hydroxy-2-chloromethylimidazo[1,2-a]pyridinium salts, which have an hemiaminal structure. However, the conformers obtained from a dihedral angle analysis performed upon these hemiaminal structures showed relatively small differences in energy among them, indicating that the hydrogen bonding interaction is not entirely responsible for preventing the aromatization process. Calculations were carried out on the gas phase of the hemiaminal cation 6b and the corresponding fully aromatic heterocycle cation 8b. It was found that the difference in energy between the two species is rather small, suggesting that other factors must be contributing to the hemiaminal isolation. The fact that a hydrogen bond is a stabilizing element of the hemiaminal suggests that the formation process of this compound should be favored in aprotic solvents. Accordingly, the condensation of several 2-aminopyridines with 3-bromo-1,1,1-trifluoroacetone was revised. The reaction performed in dry acetone (a non-competing hydrogen bond solvent) proceeded to the hemiaminal derivative, thus confirming the prediction made by theoretical calculations. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.05.044

文献信息

• Research on heterocyclic compounds. XX. Synthesis of trifluoromethyl derivatives of fused imidazole systems
  作者：Enrico Abignente、Paolo de Caprariis、Rosaria Patscot、Antonella Sacchi

  DOI：10.1002/jhet.5570230413

  日期：1986.7

  A series of heterocyclic compounds having an imidazole ring fused with another ring with a bridgehead nitrogen atom and bearing a trifluoromethyl moiety was synthesized by reaction of 3-bromo-1,1,1-trifluoroacetone with various heteroarylamines. In some cases, an intermediate compound obtained together with the required product was isolated and its structure was elucidated: e.g., starting from 2-aminopyridine

  通过3-溴-1,1,1-三氟丙酮与各种杂芳基胺的反应合成了一系列具有咪唑环的杂环化合物，所述咪唑环与另一个带有桥头氮原子的环稠合并且带有三氟甲基部分。在某些情况下，分离出与所需产物一起获得的中间体化合物，并阐明其结构：例如，从2-氨基吡啶开始，我们获得了2-三氟甲基咪唑并[1,2-a]吡啶和2-羟基-2-三氟甲基-2，3-二氢-1 H-咪唑并[1,2- a ]溴化吡啶鎓。这样的结果证实了先前提出的用于该反应的机理。