[5-(3-methoxyphenyl)-1-propylpiperidin-3-yl]methanol | 97000-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: [5-(3-methoxyphenyl)-1-propylpiperidin-3-yl]methanol
• CAS: 97000-27-6；97000-28-7
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: WVWJGUWEJLNLCU-UHFFFAOYSA-N

物化性质

• 沸点：
  370.8±37.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [5-(3-methoxyphenyl)-1-propylpiperidin-3-yl]methanol 在 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 1.08h， 生成 cis-3-(3-methoxyphenyl)-5-((methylmercapto)methyl)-N-n-propylpiperidine
  参考文献：
  名称：

  Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)methyl-substituted derivative of(.+-.)-3-PPP [3-(3-hydroxyphenyl)-1-propylpiperidine]

  摘要：

  In an attempt to enhance the potency of the dopamine autoreceptor agonist 3-PPP, racemic cis-3-(3-hydroxyphenyl)-5-[(methylmercapto)methyl]-N-n-propylpiperidine has been prepared in a stereoselective synthesis. NMR studies of 3 show a diequatorial conformation for the 3- and 5-substituents, which gives compound 3 an intriguing overlap with the ergoline derivative pergolide. Pharmacological testing revealed that 3, which is a 5-(methylmercapto)methyl derivative of racemic 3-PPP does not show the anticipated potency increase as a dopamine autoreceptor agonist. In vitro (inhibition of tyrosine hydroxylation) 3 and 1 have similar potency, and the in vivo potency (inhibition of GBL accelerated dopamine synthesis) of 3 is inferior to that of 1.

  DOI：

  10.1021/jm00147a046
• 作为产物：
  描述：

  氯化烟碱盐酸盐 在 platinum(IV) oxide 盐酸 、 六甲基磷酰三胺 、 sodium tetrahydroborate 、 potassium permanganate 、 lithium aluminium tetrahydride 、 四(三苯基膦)钯 、 氢气 、 溴 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 为溶剂， 25.0 ℃ 、344.73 kPa 条件下， 反应 48.5h， 生成 [5-(3-methoxyphenyl)-1-propylpiperidin-3-yl]methanol
  参考文献：
  名称：

  Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)methyl-substituted derivative of(.+-.)-3-PPP [3-(3-hydroxyphenyl)-1-propylpiperidine]

  摘要：

  In an attempt to enhance the potency of the dopamine autoreceptor agonist 3-PPP, racemic cis-3-(3-hydroxyphenyl)-5-[(methylmercapto)methyl]-N-n-propylpiperidine has been prepared in a stereoselective synthesis. NMR studies of 3 show a diequatorial conformation for the 3- and 5-substituents, which gives compound 3 an intriguing overlap with the ergoline derivative pergolide. Pharmacological testing revealed that 3, which is a 5-(methylmercapto)methyl derivative of racemic 3-PPP does not show the anticipated potency increase as a dopamine autoreceptor agonist. In vitro (inhibition of tyrosine hydroxylation) 3 and 1 have similar potency, and the in vivo potency (inhibition of GBL accelerated dopamine synthesis) of 3 is inferior to that of 1.

  DOI：

  10.1021/jm00147a046