(4aS,10aR)-6-Methoxy-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline

• 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: (4aS,10aR)-6-Methoxy-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline
• 英文别名: (4aS,10aR)-6-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinoline
• 化学式: C₁₄H₁₉NO
• 分子量: 217.311
• InChiKey: XGPVZNWBBGCYKA-WCQYABFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aS,10aR)-6-Methoxy-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline 在 偶氮二异丁腈 、 氢溴酸 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 生成
  参考文献：
  名称：

  cis- and trans-N-Benzyl-octahydrobenzo[g]quinolines. Adrenergic and Dopaminergic Activity Studies

  摘要：

  In vitro assays on a series of cis- and trans-octahydrobenzo[g]quinolines indicated an unusual trend of affinities at the dopaminergic receptors and ct adrenoceptors. The trans N-benzyl analogues exhibited affinity at the alpha (2) as well as the D1-like receptors whereas their N-unsubstituted congeners showed a distinct preference for the alpha (2) adrenoceptor. Enhanced activity for the alpha (2) receptors was also exhibited by the cia N-benzylated isomers. These observations are interpreted by theoretical calculations. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00076-2
• 作为产物：
  描述：

  6-methoxy-3-(2'-(methoxycarbonyl)ethyl)-2-tetralone 在 palladium on activated charcoal sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氢气 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 (4aS,10aR)-6-Methoxy-1,2,3,4,4a,5,10,10a-octahydro-benzo[g]quinoline
  参考文献：
  名称：

  cis- and trans-N-Benzyl-octahydrobenzo[g]quinolines. Adrenergic and Dopaminergic Activity Studies

  摘要：

  In vitro assays on a series of cis- and trans-octahydrobenzo[g]quinolines indicated an unusual trend of affinities at the dopaminergic receptors and ct adrenoceptors. The trans N-benzyl analogues exhibited affinity at the alpha (2) as well as the D1-like receptors whereas their N-unsubstituted congeners showed a distinct preference for the alpha (2) adrenoceptor. Enhanced activity for the alpha (2) receptors was also exhibited by the cia N-benzylated isomers. These observations are interpreted by theoretical calculations. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00076-2

文献信息

• Stereoselective synthesis of methoxy substituted 1,2,3,4,4a,5,10,10a-octahydrobenzo[g]quinolines
  作者：Charlotta Mellin、Uli Hacksell

  DOI：10.1016/s0040-4020(01)87725-5

  日期：1987.1

  The preparation of the cis- and trans-isomers of 6- and 9-methoxy-1,2,3,4,4a,5,10,10a-octahydrobenzo[g]-quinoline is reported. The syntheses involved reductions of cyclic iminium chlorides, which afforded the diastereomers conveniently and in good yields. Small cis/trans ratios were obtained with NaCNBH3 as the reducing agent. Catalytic hydrogenation using PtO2 in THF or t-BuOH gave the largest cis/trans

  报道了6-和9-甲氧基-1,2,3,4,4a，5,10,10a-八氢苯并[g]-喹啉的顺式和反式异构体的制备。合成涉及环状亚氯化亚胺的还原，这方便地且以高收率提供了非对映异构体。用NaCNBH 3作为还原剂可获得小的顺式/反式比率。使用PtO 2在THF或t-BuOH中的催化加氢得到最大的顺式/反式比。制备N-苄基衍生物以允许确定相对立体化学。
• MELLIN, CHARLOTTA;HACKSELL, ULI, TETRAHEDRON, 43,(1987) N 22, 5443-5450
  作者：MELLIN, CHARLOTTA、HACKSELL, ULI

  DOI：——

  日期：——
• SEILER, MAX PETER
  作者：SEILER, MAX PETER

  DOI：——

  日期：——
• US4692453A
  申请人：——

  公开号：US4692453A

  公开（公告）日：1987-09-08