7-(4-chlorophenoxy)heptanenitrile | 875923-65-2

• 英文名称: 7-(4-chlorophenoxy)heptanenitrile
• CAS: 875923-65-2
• 化学式: C₁₃H₁₆ClNO
• 分子量: 237.729
• InChiKey: PLIIYFPHYXYKDG-UHFFFAOYSA-N

物化性质

• 沸点：
  386.0±22.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  33.02
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-(4-chlorophenoxy)heptanenitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 异戊醇 为溶剂， 反应 16.5h， 生成 N-[7-(4-chlorophenoxy)heptyl]-1H-benzimidazol-2-amine
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063
• 作为产物：
  描述：

  7-溴庚腈 、 对氯苯酚 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以98%的产率得到7-(4-chlorophenoxy)heptanenitrile
  参考文献：
  名称：

  Synthesis and biological evaluation of new non-imidazole H3-receptor antagonists of the 2-aminobenzimidazole series

  摘要：

  A novel series of non-imidazole H-3-receptor antagonists was developed, by chemical modification of a potent lead H-3-antagonist composed by an imidazole ring connected through an alkyl spacer to a 2-aminobenzimidazole moiety (e.g., 2-[[3-[4(5)-imidazolyl]propyl]amino]benzimidazole), previously reported by our research group. We investigated whether the removal of the imidazole ring could allow retaining high affinity for the H-3-receptor, thanks to the interactions undertaken by the 2-aminobenzimidazole moiety at the binding site. The imidazole ring of the lead was replaced by a basic piperidine or by a lipophilic p-chlorophenoxy substituent, modulating the spacer length from three to eight methylene groups; moreover, the substituents were moved to the 5(6) position of the benzimidazole nucleus. Within both the 2-alkylaminobenzimidazole series and the 5(6)-alkoxy-2-amino-benzimidazole one, the greatest H-3-receptor affinity was obtained for the piperidine-substituted compounds, while the presence of the p-chlorophenoxy group resulted in a drop in affinity. The optimal chain length was different in the two series. Even if the new compounds did not reach the high receptor affinity shown by the imidazole-containing lead compound, it was possible to get good H-3-antagonist potencies with 2-aminobenzimidazoles having a tertiary amino group at appropriate distance. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.063