6-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine hydrochloride | 1172561-55-5

• 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: 6-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine hydrochloride
• 英文别名: 6-bromo-2-(chloromethyl)imidazo[1,2-a]pyridine;hydrochloride
• CAS: 1172561-55-5
• 化学式: C₈H₆BrClN₂*ClH
• mdl: MFCD10697624
• 分子量: 281.967
• InChiKey: ZSZPMWPHFPYFBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  17.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2,3-dihydro-2-hydroxy-6-bromo-2-(chloromethyl)imidazo[1,2-a]pyridine hydrochloride 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 生成 6-Bromo-2-(chloromethyl)imidazo[1,2-a]pyridine hydrochloride
  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

• Intramolecular hydrogen bond stabilization of hemiaminal structures, precursors of imidazo[1,2-a]pyridine
  作者：Manuel Velázquez、Héctor Salgado-Zamora、Cuauhtémoc Pérez、Ma Elena Campos-A、Patricia Mendoza、Hugo Jiménez、Rogelio Jiménez

  DOI：10.1016/j.molstruc.2010.05.044

  日期：2010.8

  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.