(S)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizin-2-one | 136657-36-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (S)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizin-2-one
• 英文别名: (11bS)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydrobenzo[a]quinolizin-2-one
• CAS: 136657-36-8
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: RTZZLKNSTLYSOA-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  (S)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizin-2-one 在 氘氧化钠 作用下， 以 1,4-二氧六环 、 重水 为溶剂， 反应 3.0h， 以80%的产率得到1,1,3,3-d4-2-oxo-9,10-dimethoxy-1,2,3,4,6,7-hexahydro-11bH-benzoquinolizine
  参考文献：
  名称：

  3-亚苄基苯并[a]喹啉中B/C环连接的立体化学

  摘要：

  已发现 3-苄基苯并[a]喹啉中存在反式 B/C 环连接。部分氘化化合物的 1H NMR 分析表明，4.0-4.2 ppm 处的信号应归属于 H-4-exo 质子。

  DOI：

  10.1002/mrc.1260250805
• 作为产物：
  描述：

  ((S)-1-tert-Butoxymethyl-2-methyl-propyl)-[1-(6,7-dimethoxy-3,4-dihydro-1H-isoquinolin-2-yl)-meth-(E)-ylidene]-amine 在 camphor-10-sulfonic acid 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 (S)-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-benzoquinolizin-2-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

• Pyrido [2,1-a] isoquinoline derivatives
  申请人：——

  公开号：US20040259902A1

  公开（公告）日：2004-12-23

  The present invention relates to compounds of formula (I) 1 wherein R 1 is as defined in the description, and pharmaceutically acceptable salts thereof. The compounds are useful for the treatment and/or prophylaxis of diseases which are associated with DPP-IV, such as diabetes, particularly non-insulin dependent diabetes mellitus, and impaired glucose tolerance.

  本发明涉及式(I)化合物，其中R1如描述中所定义，并且其药学上可接受的盐。该化合物可用于治疗和/或预防与DPP-IV相关的疾病，如糖尿病，特别是非胰岛素依赖性糖尿病和糖耐量受损。
• RUBIRALTA, MARIO;DIEZ, ANNA;BALET, ANTONIA;BOSCH, JOAN, TETRAHEDRON, 43,(1987) N 13, 3021-3030
  作者：RUBIRALTA, MARIO、DIEZ, ANNA、BALET, ANTONIA、BOSCH, JOAN

  DOI：——

  日期：——
• HEXAHYDROPYRIDOISOQINOLINES AS DPP-IV INHIBITORS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1638968B1

  公开（公告）日：2009-07-29
• US7718666B2
  申请人：——

  公开号：US7718666B2

  公开（公告）日：2010-05-18
• 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.

表征谱图