(+/-)-(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-3-(methoxycarbonyl)benzoquinoline | 87056-65-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (+/-)-(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-3-(methoxycarbonyl)benzoquinoline
• 英文别名: (+/-)-(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-3-(methoxycarbonyl)benzo[g]quinoline
• CAS: 87056-65-3
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: ZBWWOTROKLWPOH-SCRDCRAPSA-N

物化性质

• 沸点：
  417.2±45.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (+/-)-(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-3-(methoxycarbonyl)benzoquinoline 在 palladium on activated charcoal 盐酸 、 氢气 、 三溴化硼 、 一水合肼 、 亚硝酰氯 、 三乙胺 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：

  (+/-)-(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-1,6-dimethoxy-3-(methoxycarbonyl)benzoquinoline 在 溶剂黄146 、 锌 作用下， 生成 (+/-)-(3α,4aα,10aβ)-1,2,3,4,4a,5,10,10a-octahydro-6-methoxy-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

文献信息

• Development of an asymmetric formal synthesis of (−)-quinagolide <i>via</i> enzymatic resolution and stereoselective iminium ion reduction
  作者：Lucrezia Margherita Comparini、Andrea Menichetti、Lucilla Favero、Sebastiano Di Pietro、Fabrizio Badalassi、Per Ryberg、Mauro Pineschi

  DOI：10.1039/d3ob00946g

  日期：——

  stereoselective reduction of a diastereoisomeric mixture of benzo[g]octahydroquinolinium ion was examined in detail. A diastereoselective borohydride reduction in combination with an efficient deacylative enzymatic resolution of its β-aminoester precursor are the key steps for a stereoselective installation of the three chiral centres present in the (3S,4aS,10aR)-eutomer of the medicinal drug quinagolide. The

  详细研究了苯并[ g ]八氢喹啉鎓离子的非对映异构混合物的立体选择性还原。非对映选择性硼氢化物还原与其 β-氨基酯前体的有效脱酰酶解相结合是立体选择性安装药物 (3 S ,4a S ,10a R )-eutomer中存在的三个手性中心的关键步骤喹高利特。获得的数据为简单实用地获得手性3-取代八氢苯并[ g ]喹啉铺平了道路，手性3-取代八氢苯并[g]喹啉是药物化学中的特殊结构。
• 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).