(R)-N-(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)acetamide | 502612-50-2

• 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: (R)-N-(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)acetamide
• 英文别名: N-[(8R)-2-methyl-5,6,7,8-tetrahydroquinolin-8-yl]acetamide
• CAS: 502612-50-2
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: ZSQAMSXTKYJJCC-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酸乙酯 、 2-methyl-5,6,7,8-tetrahydroquinolin-8-ylamine 在 Candida antarctica lipase B 作用下， 以 异丙醚 为溶剂， 反应 9.0h， 生成 (R)-2-methyl-5,6,7,8-tetrahydroquinolin-8-ylamine 、 (S)-2-methyl-5,6,7,8-tetrahydroquinolin-8-ylamine 、 (R)-N-(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)acetamide 、 (S)-N-(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)acetamide
  参考文献：
  名称：

  Enzymatic Resolution of Bicyclic 1-Heteroarylamines Using Candida antarctica Lipase B

  摘要：

  Candida antarctica lipase B has been used to kinetically resolve a structurally diverse series of bicyclic 1-heteroaryl primary amines by enantioselective acetylation. High yields of either enantiomer could be obtained with excellent enantioselectivity (90-99% ee), while the undesired enantiomer could, in some cases be recycled by thermal racemization. The absolute stereochemistry of the products was confirmed by an X-ray crystal structure.

  DOI：

  10.1021/jo026701r

文献信息

• Synthesis of enantiomerically pure amino-substituted fused bicyclic rings
  申请人：——

  公开号：US20030114679A1

  公开（公告）日：2003-06-19

  This invention describes various processes for synthesis and resolution of racemic amino-substituted fused bicyclic ring systems. One process utilizes selective hydrogenation of an amino-substituted fused bicyclic aromatic ring system. An alternative process prepares the racemic amino-substituted fused bicyclic ring system via nitrosation. In addition, the present invention describes the enzymatic resolution of a racemic mixture to produce the (R)- and (S)-forms of amino-substituted fused bicyclic rings as well as a racemization process to recycle the unpreferred enantioner. Further provided by this invention is an asymmetric synthesis of the (R)- or (S)-enantiomer of primary amino-substituted fused bicyclic ring systems.

  该发明描述了合成和分离外消旋氨基取代的融合双环环系统的各种过程。其中一种过程利用选择性氢化氨基取代的融合双环芳香环系统。另一种替代过程通过亚硝化制备外消旋氨基取代的融合双环环系统。此外，该发明描述了酶催化拆分外消旋混合物，以生产氨基取代的融合双环环的(R)-和(S)-形式，以及一个消旋过程来回收未优选的对映体。该发明还提供了外消旋氨基取代的融合双环环系统的(R)-或(S)-对映体的不对称合成。
• US6825351B2
  申请人：——

  公开号：US6825351B2

  公开（公告）日：2004-11-30
• US7135570B2
  申请人：——

  公开号：US7135570B2

  公开（公告）日：2006-11-14
• US7452994B2
  申请人：——

  公开号：US7452994B2

  公开（公告）日：2008-11-18
• Enzymatic Resolution of Bicyclic 1-Heteroarylamines Using <i>Candida antarctica</i> Lipase B
  作者：Krystyna A. Skupinska、Ernest J. McEachern、Ian R. Baird、Renato T. Skerlj、Gary J. Bridger

  DOI：10.1021/jo026701r

  日期：2003.5.1

  Candida antarctica lipase B has been used to kinetically resolve a structurally diverse series of bicyclic 1-heteroaryl primary amines by enantioselective acetylation. High yields of either enantiomer could be obtained with excellent enantioselectivity (90-99% ee), while the undesired enantiomer could, in some cases be recycled by thermal racemization. The absolute stereochemistry of the products was confirmed by an X-ray crystal structure.