N-(1-methyl-1H-benzoimidazol-2-yl)-diacetamide | 17228-39-6

• 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: N-(1-methyl-1H-benzoimidazol-2-yl)-diacetamide
• 英文别名: N-acetyl-N-(1-methylbenzimidazol-2-yl)acetamide
• CAS: 17228-39-6
• 化学式: C₁₂H₁₃N₃O₂
• 分子量: 231.254
• InChiKey: VBCHPMGWNJGSFT-UHFFFAOYSA-N

物化性质

• 沸点：
  383.8±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰氯 、 2-氨-1-甲基苯咪唑 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94 mg的产率得到N-(1-甲基-1H-苯并[d]咪唑-2-基)-乙酰胺
  参考文献：
  名称：

  Intramolecular Hydrogen Bonding in Medicinal Chemistry

  摘要：

  The formation of intramolecular hydrogen bonds has a very pronounced effect on molecular structure and properties. We study both aspects in detail with the aim of enabling a more rational use of this class of interactions in medicinal chemistry. On the basis of exhaustive searches in crystal structure databases, we derive propensities for intramolecular hydrogen bond formation of five- to eight-membered ring systems of relevance in drug discovery. A number of motifs, several of which arc clearly underutilized in drug discovery, are analyzed in more detail by comparing small molecule and protein ligand X-ray structures. To investigate effects on physicochemical properties, sets of closely related structures with and without the ability to form intramolecular hydrogen bonds were designed, synthesized, and characterized with respect to membrane permeability, water solubility, and lipophilicity. We find that changes in these properties depend on a subtle balance between the strength of the hydrogen bond interaction, geometry of the newly formed ring system, and the relative energies of the open and closed conformations in polar and unpolar environments. A number of general guidelines for medicinal chemists emerge from this study.

  DOI：

  10.1021/jm100087s