(+/-)-2,3-dimethoxy-5,6,8,8a,9,10,13,13a-octahydro-11H-dibenzoquinolizin-1-one | 19778-10-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: (+/-)-2,3-dimethoxy-5,6,8,8a,9,10,13,13a-octahydro-11H-dibenzoquinolizin-1-one
• 英文别名: 2,3-dimethoxy-5,6,8,8a,9,10,13,13a-octahydro-11 H-dibenzoquinolizin-11-one；11H-Dibenzo[a,g]quinolizin-11-one, 5,6,8,8a,9,10,13,13a-octahydro-2,3-dimethoxy-；2,3-dimethoxy-5,6,8,8a,9,10,13,13a-octahydroisoquinolino[2,1-b]isoquinolin-11-one
• CAS: 19778-10-0；55090-58-9；136657-33-5
• 化学式: C₁₉H₂₃NO₃
• 分子量: 313.397
• InChiKey: KIJMJVNSLOIVHT-UHFFFAOYSA-N

物化性质

• 沸点：
  481.9±45.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-(-)-(3-methoxybenzyl)-1,2,3,4-tetrahydroisoquinoline 在 氨 、 水 、 sodium 、 溶剂黄146 、 叔丁醇 作用下， 反应 3.25h， 生成 (+/-)-2,3-dimethoxy-5,6,8,8a,9,10,13,13a-octahydro-11H-dibenzoquinolizin-1-one
  参考文献：
  名称：

  Asymmetric synthesis of benzoquinolizidines: a formal synthesis of (-)-emetine

  摘要：

  Chiral formamidines affixed to tetrahydroisoquinoline derivatives affords the appropriate precursor 9 to various benzo[a]quinolizidines 2 and 3 and dibenzo[a,g]quinolizidines 4 in modest to high optical purity. Both 3 and 4 have been utilized in total syntheses of natural emetine 1, thus the route herein constitutes a formal total synthesis of 1. Furthermore, Mannich cyclizations of 1-alkylisoquinolines 18a-c proceeded with or without loss of absolute stereochemistry at the C-1 position. Explanation for this behavior is based upon whether a [3,3] rearrangement or a Mannich reaction takes place. The former results in virtually complete racemization of 18, whereas the latter totally conserves the chirality in 18. Finally, 1-alkynylisoquinolines of high optical purity were transformed, via the Overman protocol, to alkylidine benzo[a]quinolizidines 24 in good yield and to our knowledge, high enantiomeric excess.

  DOI：

  10.1021/jo00024a032

文献信息

• Akhrem, A. A.; Chernov, Yu. G., Doklady Chemistry, 1986, vol. 291, p. 488 - 489
  作者：Akhrem, A. A.、Chernov, Yu. G.

  DOI：——

  日期：——
• AXREM, A. A.;CHERNOV, YU. G.
  作者：AXREM, A. A.、CHERNOV, YU. G.

  DOI：——

  日期：——
• Asymmetric synthesis of benzoquinolizidines: a formal synthesis of (-)-emetine
  作者：Joseph W. Guiles、A. I. Meyers

  DOI：10.1021/jo00024a032

  日期：1991.11

  Chiral formamidines affixed to tetrahydroisoquinoline derivatives affords the appropriate precursor 9 to various benzo[a]quinolizidines 2 and 3 and dibenzo[a,g]quinolizidines 4 in modest to high optical purity. Both 3 and 4 have been utilized in total syntheses of natural emetine 1, thus the route herein constitutes a formal total synthesis of 1. Furthermore, Mannich cyclizations of 1-alkylisoquinolines 18a-c proceeded with or without loss of absolute stereochemistry at the C-1 position. Explanation for this behavior is based upon whether a [3,3] rearrangement or a Mannich reaction takes place. The former results in virtually complete racemization of 18, whereas the latter totally conserves the chirality in 18. Finally, 1-alkynylisoquinolines of high optical purity were transformed, via the Overman protocol, to alkylidine benzo[a]quinolizidines 24 in good yield and to our knowledge, high enantiomeric excess.