5-(N-ethyl-N-methyl)amino-5,6,7,8-tetrahydro-5-quinoline | 185510-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 5-(N-ethyl-N-methyl)amino-5,6,7,8-tetrahydro-5-quinoline
• 英文别名: N-ethyl-N-methyl-5,6,7,8-tetrahydroquinolin-5-amine
• CAS: 185510-56-9
• 化学式: C₁₂H₁₈N₂
• 分子量: 190.288
• InChiKey: STJUNYXASPJZGY-UHFFFAOYSA-N

物化性质

• 沸点：
  287.6±28.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  16.13
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(N-ethyl-N-methyl)amino-5,6,7,8-tetrahydro-5-quinoline 在 盐酸 作用下， 以 乙醚 为溶剂， 以24%的产率得到
  参考文献：
  名称：

  Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation

  摘要：

  Because the structural requirements for the binding of nicotine to central nicotine receptors remain largely uninvestigated, we undertook a systematic investigation of pyrrolidine ring-opened analogs. This led to a subsequent investigation of related conformationally restricted derivatives of these analogs. The results are reported relative to the binding of several well-known and widely used nicotine receptor ligands. Although none of the ring-opened analogs binds with higher affinity than (-)nicotine (K-i = 2.3 nM), 3-(N-methyl-N-ethylaminomethyl)pyridine (12a; K-i = 28 nM) binds with significant affinity. A conformationally restricted analog of 12a, N-methyl [2,7]naphthyridine 30b (K-i = 18 nM), binds with similar affinity. 6-Substitution of 12a and racemic nicotine seems to be tolerated when the substituent is halogen or methyl. In functional studies (hypolocomotion and antinociception in mice; stimulus generalization in nicotine-trained rats) 30b retains nicotine-like properties. Several of the 6-substituted compounds were 2 to 20 times more potent than (+/-)nicotine. Although the intact pyrrolidine ring of nicotine appears important for optimal affinity, its pre presence is not an absolute requirement for activity, and 6-position substitution of the pyridine nucleus can influence both binding and functional activity.

  DOI：

  10.1016/s0223-5234(97)89850-9
• 作为产物：
  描述：

  5,6,7,8-四氢喹啉-5-酮 在 lithium aluminium tetrahydride 、 ammonium acetate 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 、 甲苯 、 乙腈 为溶剂， 反应 67.83h， 生成 5-(N-ethyl-N-methyl)amino-5,6,7,8-tetrahydro-5-quinoline
  参考文献：
  名称：

  Pyrrolidine-modified and 6-substituted analogs of nicotine: A structure—affinity investigation

  摘要：

  Because the structural requirements for the binding of nicotine to central nicotine receptors remain largely uninvestigated, we undertook a systematic investigation of pyrrolidine ring-opened analogs. This led to a subsequent investigation of related conformationally restricted derivatives of these analogs. The results are reported relative to the binding of several well-known and widely used nicotine receptor ligands. Although none of the ring-opened analogs binds with higher affinity than (-)nicotine (K-i = 2.3 nM), 3-(N-methyl-N-ethylaminomethyl)pyridine (12a; K-i = 28 nM) binds with significant affinity. A conformationally restricted analog of 12a, N-methyl [2,7]naphthyridine 30b (K-i = 18 nM), binds with similar affinity. 6-Substitution of 12a and racemic nicotine seems to be tolerated when the substituent is halogen or methyl. In functional studies (hypolocomotion and antinociception in mice; stimulus generalization in nicotine-trained rats) 30b retains nicotine-like properties. Several of the 6-substituted compounds were 2 to 20 times more potent than (+/-)nicotine. Although the intact pyrrolidine ring of nicotine appears important for optimal affinity, its pre presence is not an absolute requirement for activity, and 6-position substitution of the pyridine nucleus can influence both binding and functional activity.

  DOI：

  10.1016/s0223-5234(97)89850-9