(+/-)-(3α,4aα,10aβ)-3-(tertbutoxycarbonyl)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxybenzo(g)quinoline | 87098-97-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (+/-)-(3α,4aα,10aβ)-3-(tertbutoxycarbonyl)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxybenzo(g)quinoline
• 英文别名: (+/-)-(3α,4aα,10aβ)-3-(tertbutoxycarbonyl)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxybenzoquinoline；(+/-)-(3α,4aα,10aβ)-3-(tertbutoxycarbonyl)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxybenzo[g]quinoline
• CAS: 87098-97-3
• 化学式: C₂₀H₂₉NO₄
• 分子量: 347.455
• InChiKey: UFKPKIGNJVDDIL-UXLLHSPISA-N

物化性质

• 沸点：
  451.5±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.0
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 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：

  (+/-)-(3α,4aα,10aβ)-3-(tertbutoxycarbonyl)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxybenzo(g)quinoline 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 三溴化硼 、 一水合肼 、 溶剂黄146 、 亚硝酰氯 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 丙醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 28.0h， 生成 quinagolide
  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：

  tert-butyl 3-(1,2,3,4-tetrahydro-2-oxo-3-naphthyl)-2-methylenepropionate 在 盐酸 、 disodium hydrogenphosphate 、 potassium dihydrogenphosphate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 79.0h， 生成 (+/-)-(3α,4aα,10aβ)-3-(tertbutoxycarbonyl)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxybenzo(g)quinoline
  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

文献信息

• Resolution and absolute configuration of the potent dopamine agonist N,N-diethyl-N'-[(3.alpha.,4a.alpha.,10a.beta.)-1,2,3,4,4a,5,10,10a-octahydro-6-hydroxy-1-propyl-3-benzo[g]quinolinyl]sulfamide
  作者：Rene Nordmann、Armin Widmer

  DOI：10.1021/jm00148a030

  日期：1985.10

  The synthesis and preliminary pharmacological evaluation of the optical antipodes of the title compound (+/-)-1 (CV 205-502) is presented. The dopaminomimetic activity is shown to reside entirely in the (-) enantiomer. Crystallographic analysis has proven that the absolute configuration of the active (-) enantiomer corresponds to that of its ergoline analogue 3 (CQ 32-084) and of apomorphine (5).