(+/-)-3-(2,5-dimethoxyphenyl)piperidin-2-one | 150129-95-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (+/-)-3-(2,5-dimethoxyphenyl)piperidin-2-one
• 英文别名: 3-(2,5-Dimethoxyphenyl)piperidin-2-one
• CAS: 150129-95-6；150129-96-7；150129-97-8
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: RZAMMSKFEPBJHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-(2,5-dimethoxyphenyl)piperidin-2-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 18.0h， 以84%的产率得到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：

  (+/-)-ethyl (2-cyanoethyl)(2,5-dimethoxyphenyl)acetate 在 platinum(IV) oxide 、 palladium on activated charcoal 氨 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以68%的产率得到(+/-)-3-(2,5-dimethoxyphenyl)piperidin-2-one
  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

文献信息

• 2,5-Dimethoxy congeners of (+)- and (-)-3-(3-hydroxyphenyl)-N-n-propylpiperidine
  作者：Joseph G. Cannon、Karen S. Kirschbaum、Victor E. D. Amoo、Alan K. Johnson、John Paul Long

  DOI：10.1021/jm00068a021

  日期：1993.8

  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.