5-(3-甲氧基苯基)吡啶-3-甲酸甲酯 | 97000-24-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-(3-甲氧基苯基)吡啶-3-甲酸甲酯
• 英文名称: methyl 5-(3-methoxyphenyl)nicotinate
• 英文别名: methyl 5-(3-methoxyphenyl)pyridine-3-carboxylate
• CAS: 97000-24-3
• 化学式: C₁₄H₁₃NO₃
• 分子量: 243.262
• InChiKey: XIHHVNOLKZCWEN-UHFFFAOYSA-N

物化性质

• 沸点：
  384.7±32.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  48.4
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-(3-甲氧基苯基)吡啶-3-甲酸甲酯 在 platinum(IV) oxide 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醇 、 水 为溶剂， 55.0 ℃ 、344.73 kPa 条件下， 反应 28.08h， 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：

  3-溴吡啶-5-甲醇 在 盐酸 、 六甲基磷酰三胺 、 potassium permanganate 、 四(三苯基膦)钯 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 5-(3-甲氧基苯基)吡啶-3-甲酸甲酯
  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

文献信息

• Synthesis and dopamine autoreceptor activity of a 5-(methylmercapto)methyl-substituted derivative of(.+-.)-3-PPP [3-(3-hydroxyphenyl)-1-propylpiperidine]
  作者：T. Ross Kelly、Harry R. Howard、B. Kenneth Koe、Reinhard Sarges

  DOI：10.1021/jm00147a046

  日期：1985.9

  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.