(+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzoquinoline | 87479-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzoquinoline
• 英文别名: (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzo[g]quinoline
• CAS: 87479-83-2
• 化学式: C₁₇H₂₃NO₄
• 分子量: 305.374
• InChiKey: JLCSYSYTJSTZIU-YDHLFZDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  48.0
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzoquinoline 在 吡啶 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-<(methylthio)methyl>benzoquinoline
  参考文献：
  名称：

  Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine

  摘要：

  A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.

  DOI：

  10.1021/jm00381a017
• 作为产物：
  描述：

  (+/-)-(3α,4aα,10aβ)-3-(tertbutoxycarbonyl)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxybenzo(g)quinoline 在 sodium hydroxide 、 硫酸 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 (+/-)-(3β,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzoquinoline
  参考文献：
  名称：

  Octahydrobenzo[g]quinolines: potent dopamine agonists which show the relationship between ergolines and apomorphine

  摘要：

  A synthesis of all four diastereoisomeric 3-(tert-butoxycarbonyl)-1,6-dimethoxyoctahydrobenzo[g]quinolines 13a-d is presented. The two trans isomers 13b and 13c have been converted to tricyclic analogues 20 (CV 205-502) and 26 (205-503) of the potent dopaminomimetic ergolines CQ 32-084 and pergolide, respectively. These two compounds combine the essential moiety of apomorphine with the important 8-substituents of ergolines. Preliminary pharmacological evaluation of 20 and 26 suggests that these novel dopamine agonists combine the specificity of apomorphine with the potency, long duration of action, and good oral activity of the ergolines.

  DOI：

  10.1021/jm00381a017