N-(1,1-Dimethyl-propyl)-N'-[4-(1H-imidazol-4-yl)-phenyl]-formamidine; hydrochloride | 133753-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(1,1-Dimethyl-propyl)-N'-[4-(1H-imidazol-4-yl)-phenyl]-formamidine; hydrochloride
• CAS: 133753-33-0
• 化学式: C₁₅H₂₀N₄*2ClH
• 分子量: 329.272
• InChiKey: FVCWYAKXRZKTBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.94
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.07
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-(1,1-二甲基丙基)甲酰胺 、 4-(1H-咪唑-4-基)苯胺盐酸盐 以52.3%的产率得到N-(1,1-Dimethyl-propyl)-N'-[4-(1H-imidazol-4-yl)-phenyl]-formamidine; hydrochloride
  参考文献：
  名称：

  Substituent effect on the stereochemistry of H2-receptor antagonists of the phenylformamidine series. A conformation-dependent mode of interaction with the H2 receptor

  摘要：

  The influence of alkyl substitution on the stereoisomerism of the formamidine cation (E,E vs E,Z) of several N-substituted (imidazolylphenyl)formamidines (1-10) was investigated. As (imidazolylphenyl)formamidines having alkyl substituents of more than three carbon atoms bind to H-2-receptor preparations in a pseudoirreversible mode causing unsurmountable antagonism, the four isomeric butylformamidines (5-7 and 9) having comparable lipophilic character but different E,E/E,Z composition were investigated in H-2-receptor assays to determine quantitatively any difference in their pseudoirreversible inhibitory pattern. It was found that the geometry of the formamidine cation is affected by the steric bulk of the substituent on the formamidine nitrogen. A relationship between the percentage of the E,E conformation of the formamidine cation and degree of pseudoirreversible antagonism was also found. The present studies support the hypothesis that bidentate hydrogen bonding plays an important role in the interaction of (imidazolylphenyl)formamidines with the H-2 receptor.

  DOI：

  10.1021/jm00110a004