2-(2-azidoethoxy)-N,N-diethylethanamine | 136089-18-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 2-(2-azidoethoxy)-N,N-diethylethanamine
• CAS: 136089-18-4
• 化学式: C₈H₁₈N₄O
• 分子量: 186.257
• InChiKey: BQDFDHKKSJJINS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  13.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  61.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-azidoethoxy)-N,N-diethylethanamine 在 palladium on activated charcoal 氢气 、 sodium cyanoborohydride 、 碳酸氢钠 、 红铝 、 正戊烷 作用下， 以 乙醇 、 氯仿 、 水 、 甲苯 、 乙腈 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 50.0h， 生成 N-<2-<2-(diethylamino)ethoxy>ethyl>-N-methyl-1-phenyl-1-cyclopentanemethylamine
  参考文献：
  名称：

  Novel 1-phenylcycloalkanecarboxylic acid derivatives as potential anticonvulsant agents

  摘要：

  A series of analogues based on the anticonvulsant carbetapentane (1, 2-[2-(diethylamino)ethoxy]ethyl 1-phenyl-1-cyclopentylcarboxylate) was prepared as potential novel anticonvulsant drugs. Structure-activity relationships of analogues in which the ester function and cyclopentane moieties were modified have been investigated by evaluating their ability to prevent seizures in the rat maximal electroshock test. These compounds (11, ED50 = 16-mu-mol/kg; 12, ED50 = 86-mu-mol/kg, and 23, ED50 = 173-mu-mol/kg) were effective anticonvulsants. Compound 11, an alkyl ether derivative of 1, was more potent than the parent compound (ED50 = 48-mu-mol/kg) and also showed a 2-fold increase in potency compared to that of the prototypic anticonvulsant drug diphenylhydantoin.

  DOI：

  10.1021/jm00115a002
• 作为产物：
  描述：

  2-(2-二乙氨基乙氧基)乙醇 在 Zn(N3)2-2 pyr 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2-(2-azidoethoxy)-N,N-diethylethanamine
  参考文献：
  名称：

  Novel 1-phenylcycloalkanecarboxylic acid derivatives as potential anticonvulsant agents

  摘要：

  A series of analogues based on the anticonvulsant carbetapentane (1, 2-[2-(diethylamino)ethoxy]ethyl 1-phenyl-1-cyclopentylcarboxylate) was prepared as potential novel anticonvulsant drugs. Structure-activity relationships of analogues in which the ester function and cyclopentane moieties were modified have been investigated by evaluating their ability to prevent seizures in the rat maximal electroshock test. These compounds (11, ED50 = 16-mu-mol/kg; 12, ED50 = 86-mu-mol/kg, and 23, ED50 = 173-mu-mol/kg) were effective anticonvulsants. Compound 11, an alkyl ether derivative of 1, was more potent than the parent compound (ED50 = 48-mu-mol/kg) and also showed a 2-fold increase in potency compared to that of the prototypic anticonvulsant drug diphenylhydantoin.

  DOI：

  10.1021/jm00115a002