methyl (S)-1,2,3,4-tetrahydroquinoline-2-acetate | 185854-46-0

• 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: methyl (S)-1,2,3,4-tetrahydroquinoline-2-acetate
• 英文别名: (S)-methyl 2-(1,2,3,4-tetrahydroquinolin-2-yl)acetate；methyl (S)-2-(1,2,3,4-tetrahydroquinolin-2-yl)acetate；methyl 2-[(2S)-1,2,3,4-tetrahydroquinolin-2-yl]acetate
• CAS: 185854-46-0
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: HDPKJUKZQOPEOF-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (S)-1,2,3,4-tetrahydroquinoline-2-acetate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor

  摘要：

  A series of tricyclic quinoxalinediones, 5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones, were synthesized and was evaluated for their affinity for the glycine binding site of the NMDA receptor using a [H-3]- 5,7-dichlorokynurenic acid binding assay. The six-membered ring-fused tricyclic quinoxalinedione 18g (K-i = 9.9 nM) displayed high affinity for the glycine site. The anilide derivative 20g (K-i = 2.6 nM) was 4-fold more potent than 18g and as potent as L-689,560, one of the most potent glycine antagonists so far prepared. Although the carboxylic acid derivative of the corresponding five-membered ring-fused tricyclic quinoxalinedione 18e (K-i = 7.3 nM) had affinity comparable to that of 18g, the anilide derivative 20e largely decreased in the affinity in contrast to 20g. Enantiomers 23g, 24g, 25g, and 26g were prepared and tested. Only the S enantiomer 25g (K-i = 0.96 nM) retained the affinity among the anilide derivatives, whereas both enantiomers 23g (K-i = 2.3 nM) and 24g (K-i = 9.6 nM) were active among the carboxylic acid derivatives. The origin of the high affinity of carboxylic acid derivatives such as 18e and 18g would be a charge-charge interaction between the anionic carboxylate residues of the compounds and the cationic proton-donor site in the receptor.

  DOI：

  10.1021/jm00049a015
• 作为产物：
  描述：

  (S)-2-Iodomethyl-1,2,3,4-tetrahydro-quinoline 在 盐酸 、 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.5h， 生成 methyl (S)-1,2,3,4-tetrahydroquinoline-2-acetate
  参考文献：
  名称：

  Tricyclic Quinoxalinediones: 5,6-Dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-Dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones as Potent Antagonists for the Glycine Binding Site of the NMDA Receptor

  摘要：

  A series of tricyclic quinoxalinediones, 5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-diones and 6,7-dihydro-1H,5H-pyrido[1,2,3-de]quinoxaline-2,3-diones, were synthesized and was evaluated for their affinity for the glycine binding site of the NMDA receptor using a [H-3]- 5,7-dichlorokynurenic acid binding assay. The six-membered ring-fused tricyclic quinoxalinedione 18g (K-i = 9.9 nM) displayed high affinity for the glycine site. The anilide derivative 20g (K-i = 2.6 nM) was 4-fold more potent than 18g and as potent as L-689,560, one of the most potent glycine antagonists so far prepared. Although the carboxylic acid derivative of the corresponding five-membered ring-fused tricyclic quinoxalinedione 18e (K-i = 7.3 nM) had affinity comparable to that of 18g, the anilide derivative 20e largely decreased in the affinity in contrast to 20g. Enantiomers 23g, 24g, 25g, and 26g were prepared and tested. Only the S enantiomer 25g (K-i = 0.96 nM) retained the affinity among the anilide derivatives, whereas both enantiomers 23g (K-i = 2.3 nM) and 24g (K-i = 9.6 nM) were active among the carboxylic acid derivatives. The origin of the high affinity of carboxylic acid derivatives such as 18e and 18g would be a charge-charge interaction between the anionic carboxylate residues of the compounds and the cationic proton-donor site in the receptor.

  DOI：

  10.1021/jm00049a015

文献信息

• Highly Enantioselective Iridium-Catalyzed Hydrogenation of 2-Benzylquinolines and 2-Functionalized and 2,3-Disubstituted Quinolines
  作者：Da-Wei Wang、Xiao-Bing Wang、Duo-Sheng Wang、Sheng-Mei Lu、Yong-Gui Zhou、Yu-Xue Li

  DOI：10.1021/jo900073z

  日期：2009.4.3

  The enantioselective hydrogenation of 2-benzylquinolines and 2-functionalized and 2,3-disubstituted quinolines was developed by using the [Ir(COD)Cl]2/bisphosphine/I2 system with up to 96% ee. Moreover, mechanistic studies revealed the hydrogenation mechanism of quinoline involves a 1,4-hydride addition, isomerization, and 1,2-hydride addition, and the catalytic active species may be a Ir(III) complex

  通过使用[Ir（COD）Cl] 2 /双膦/ I 2体系（ee高达96％）开发了2-苄基喹啉和2-官能化和2,3-二取代喹啉的对映选择性氢化。而且，机理研究表明，喹啉的氢化机理涉及1，4-氢化物的加成，异构化和1，2-氢化物的加成，并且催化活性物质可以是与氯化物和碘化物的Ir（III）络合物。
• Enzymatic resolution of 2-substituted tetrahydroquinolines. Convenient approaches to tricyclic quinoxalinediones as potent NMDA-glycine antagonists
  作者：Seiji Katayama、Nobuyuki Ae、Ryu Nagata

  DOI：10.1016/s0957-4166(98)00484-4

  日期：1998.12

  class of NMDA-glycine antagonists using enzymatic resolutions are described. An intermediate, racemic methyl 1,2,3,4-tetrahydroquinoline-2-carboxylate 3, was resolved to (S)-3 in 97% ee and 47% yield (E=67) using α-chymotrypsin. In an improved method, hydrolysis of another intermediate, racemic methyl 1,2,3,4-tetrahydroquinoline-2-acetate 4, with Novozym® 435 provided the desired (S)-4 in high enantioselectivity

  描述了使用酶促拆分导致对映体纯的三环喹喔啉二酮类NMDA-甘氨酸拮抗剂的两种方法。使用α-胰凝乳蛋白酶将中间体1,2,3,4-四氢喹啉-2-羧酸外消旋甲基1,2,3,4-四氢喹啉-2-羧酸酯3拆分为（S）-3，收率为97％ee，收率为47％（E = 67）。在一个改进的方法中，另一种中间体，外消旋甲基-1,2,3,4-四氢喹啉-2-乙酸乙酯水解4，用的Novozym ® 435提供所需的（小号） - 4在高对映选择性和产率（93％ee的，50 ％，E = 94）。
• Chiral Helical Oligotriazoles: New Class of Anion-Binding Catalysts for the Asymmetric Dearomatization of Electron-Deficient <i>N</i>-Heteroarenes
  作者：Mercedes Zurro、Sören Asmus、Stephan Beckendorf、Christian Mück-Lichtenfeld、Olga García Mancheño

  DOI：10.1021/ja507940k

  日期：2014.10.8

  Helical chirality and selective anion-binding processes are key strategies used in nature to promote highly enantioselective chemical reactions. Although enormous efforts have been made to develop simple helical chiral systems and thus open new possibilities in asymmetric catalysis and synthesis, the efficient use of synthetic oligo- and polymeric helical chiral catalysts is still very challenging

  螺旋手性和选择性阴离子结合过程是自然界中用于促进高度对映选择性化学反应的关键策略。尽管已经为开发简单的螺旋手性体系做出了巨大的努力，从而为不对称催化和合成开辟了新的可能性，但合成低聚和聚合螺旋手性催化剂的有效使用仍然非常具有挑战性且相当不寻常。在这项工作中，结构独特的手性低聚三唑已被开发作为基于 CH 键的阴离子结合催化剂，用于 N-杂芳烃的不对称脱芳构化。这些旋转柔性催化剂在与氯阴离子结合时采用增强的手性螺旋构象，允许通过与预先形成的离子底物的紧密手性阴离子对复合物进行高水平的手性转移。
• Synthesis of (−)-(R)-angustureine by formal alkynylation of a chiral β-amino ester
  作者：Jumreang Tummatorn、Gaspar Diaz Muñoz、Gregory B. Dudley

  DOI：10.1016/j.tetlet.2012.12.122

  日期：2013.3

  A new synthesis of (-)-angustureine is described, featuring an annulation and fragmentation sequence that formally results in alkynylation of a beta-amino ester. The six-step sequence from a readily available chiral beta-amino ester to the natural product was achieved in 46% yield, with no protecting groups and three purifications. (C) 2013 Elsevier Ltd. All rights reserved.
• Highly enantioselective Ir-catalyzed hydrogenation of exocyclic enamines
  作者：Xiao-Bing Wang、Da-Wei Wang、Sheng-Mei Lu、Chang-Bin Yu、Yong-Gui Zhou

  DOI：10.1016/j.tetasy.2009.03.037

  日期：2009.5

  [Ir(COD)Cl](2)/Meo-BiPhep/I-2 catalyst system is highly effective for the asymmetric hydrogenation of exocyclic enamines with high enantioselectivities (up to 96% ee). (c) 2009 Elsevier Ltd. All rights reserved.