(+/-)-ethyl (2-cyanoethyl)(2,5-dimethoxyphenyl)acetate | 150129-94-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-ethyl (2-cyanoethyl)(2,5-dimethoxyphenyl)acetate
• 英文别名: ethyl 4-cyano-2-(2,5-dimethoxyphenyl)butanoate
• CAS: 150129-94-5
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: ZUGCGNLQHZJOJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  20.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  68.55
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-ethyl (2-cyanoethyl)(2,5-dimethoxyphenyl)acetate 在 platinum(IV) oxide 、 palladium on activated charcoal lithium aluminium tetrahydride 、 氨 、 氢气 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 31.0h， 生成 (R)-1-<(1-naphthylethyl)carbamoyl>-3-(2,5-dimethoxyphenyl)piperidine
  参考文献：
  名称：

  2,5-Dimethoxy congeners of (+)- and (-)-3-(3-hydroxyphenyl)-N-n-propylpiperidine

  摘要：

  p-Dimethoxyaryl analogs of certain potent catechol-derived dopaminergic agonists show dopaminergic properties for which no structure-activity relationship has yet been defined. (S)-3-(3-Hydroxyphenyl)-N-n-propylpiperidine (1, S-''3-PPP'') is a dopaminergic autoreceptor agonist, and at high doses it also exhibits postsynaptic antagonism. (R)-1 is a postsynaptic agonist. In a continuation of studies of effects of the p-dimethoxy moiety at dopamine receptors, synthesis and resolution of the 2,5-dimethoxy analog 3 of 3-PPP was undertaken. The two enantiomers and the racemic modification showed cardiovascular effects consistent with actions at DA-2 receptors. The potency of all three compounds was much lower than that of 3-PPP, although they displayed approximately the same duration of action. Absolute configuration does not seem to be a major determinant of these compounds' ability to interact with DA-2 receptors.

  DOI：

  10.1021/jm00068a021
• 作为产物：
  描述：

  2,5-二甲氧基苯基乙酸 在 硫酸 、 苄基三甲基氢氧化铵 作用下， 反应 11.17h， 生成 (+/-)-ethyl (2-cyanoethyl)(2,5-dimethoxyphenyl)acetate
  参考文献：
  名称：

  2,5-Dimethoxy congeners of (+)- and (-)-3-(3-hydroxyphenyl)-N-n-propylpiperidine

  摘要：

  p-Dimethoxyaryl analogs of certain potent catechol-derived dopaminergic agonists show dopaminergic properties for which no structure-activity relationship has yet been defined. (S)-3-(3-Hydroxyphenyl)-N-n-propylpiperidine (1, S-''3-PPP'') is a dopaminergic autoreceptor agonist, and at high doses it also exhibits postsynaptic antagonism. (R)-1 is a postsynaptic agonist. In a continuation of studies of effects of the p-dimethoxy moiety at dopamine receptors, synthesis and resolution of the 2,5-dimethoxy analog 3 of 3-PPP was undertaken. The two enantiomers and the racemic modification showed cardiovascular effects consistent with actions at DA-2 receptors. The potency of all three compounds was much lower than that of 3-PPP, although they displayed approximately the same duration of action. Absolute configuration does not seem to be a major determinant of these compounds' ability to interact with DA-2 receptors.

  DOI：

  10.1021/jm00068a021