N-(1,2,3,4-tetrahydroquinolin-8-yl)acetamide | 99840-76-3

• 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: N-(1,2,3,4-tetrahydroquinolin-8-yl)acetamide
• 英文别名: 8-Acetylamino-1,2,3,4-tetrahydrochinolin
• CAS: 99840-76-3
• 化学式: C₁₁H₁₄N₂O
• 分子量: 190.245
• InChiKey: KTHDNHNPVDWPBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1,2,3,4-tetrahydroquinolin-8-yl)acetamide 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-甲基-1,2,3,4-四氢-8-喹啉胺
  参考文献：
  名称：

  N-Tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl biaryl carboxamides as antagonists of TRPV1

  摘要：

  Starting from the high throughput screening hit (3), novel N-tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl carboxamides have been identified as potent antagonists of the ion channel TRPV1. The N-quinolinylnicotinamide (46) showed excellent potency at human, guinea pig and rat TRPV1, a favourable in vitro DMPK profile and activity in an in vivo model of inflammatory pain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.026
• 作为产物：
  描述：

  N-(quinolin-8-yl)acetamide 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、344.74 kPa 条件下， 生成 N-(1,2,3,4-tetrahydroquinolin-8-yl)acetamide
  参考文献：
  名称：

  N-Tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl biaryl carboxamides as antagonists of TRPV1

  摘要：

  Starting from the high throughput screening hit (3), novel N-tetrahydroquinolinyl, N-quinolinyl and N-isoquinolinyl carboxamides have been identified as potent antagonists of the ion channel TRPV1. The N-quinolinylnicotinamide (46) showed excellent potency at human, guinea pig and rat TRPV1, a favourable in vitro DMPK profile and activity in an in vivo model of inflammatory pain. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.026

文献信息

• Boric acid catalyzed chemoselective reduction of quinolines
  作者：Dipanjan Bhattacharyya、Sekhar Nandi、Priyanka Adhikari、Bikash Kumar Sarmah、Monuranjan Konwar、Animesh Das

  DOI：10.1039/c9ob02673h

  日期：——

  Boric acid promoted transfer hydrogenation of substituted quinolines to synthetically versatile 1,2,3,4-tetrahydroquinolines (1,2,3,4-THQs) was described under mild reaction conditions using a Hantzsch ester as a mild organic hydrogen source. This methodology is practical and efficient, where isolated yields are excellent and reducible functional groups are well tolerated in the N-heteroarene moiety

  硼酸促进了取代喹啉向合成多用途的1,2,3,4-四氢喹啉（1,2,3,4-THQs）的转移加氢反应，该反应在温和的反应条件下使用汉茨酯作为温和的有机氢源进行了描述。该方法是实用且有效的，其中分离的收率极好，并且在N-杂芳烃部分中可还原的官能团具有良好的耐受性。通过各种对照实验和NMR研究证明了反应参数和初步的机理途径。目前的工作也可以扩大规模以获得克量，并且通过将1,2,3,4-THQs转化为一系列具有生物学重要性的分子（包括抗心律不齐药物nicainoprol）来说明所开发方法的实用性。
• 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。
• Concise Preparation of Amino-5,6,7,8-tetrahydroquinolines and Amino-5,6,7,8-tetrahydroisoquinolines via Catalytic Hydrogenation of Acetamidoquinolines and Acetamidoisoquinolines
  作者：Krystyna A. Skupinska、Ernest J. McEachern、Renato T. Skerlj、Gary J. Bridger

  DOI：10.1021/jo026258k

  日期：2002.11.1

  via catalytic hydrogenation of the corresponding acetamido-substituted quinolines and isoquinolines followed by acetamide hydrolysis is described. The yields of the products are good when the acetamido substituent is present on the pyridine ring and moderate with the acetamido substituent on the benzene ring. This method has also been applied to the regioselective reduction of quinoline substrates bearing

  描述了一种通过相应的乙酰胺基取代的喹啉和异喹啉的催化氢化，然后乙酰胺水解制备氨基取代的5,6,7,8-四氢喹啉和5,6,7,8-四氢异喹啉的方法。当乙酰氨基取代基存在于吡啶环上且与乙酰氨基取代基在苯环上适度结合时，产物的收率良好。此方法也已应用于带有其他取代基（R = OMe，CO（2）Me，Ph）的喹啉底物的区域选择性还原。
• EP1487795A4
  申请人：——

  公开号：EP1487795A4

  公开（公告）日：2005-02-09
• SYNTHESIS OF ENANTIOMERICALLY PURE AMINO-SUBSTITUTED FUSED BICYCLIC RINGS
  申请人：ANORMED INC.

  公开号：EP1487795A2

  公开（公告）日：2004-12-22