2-oxo-1,2,3,4-tetrahydroquinolin-3-acetaldehyde | 726187-33-3

• 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: 2-oxo-1,2,3,4-tetrahydroquinolin-3-acetaldehyde
• 英文别名: 2-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)acetaldehyde；2-(2-oxo-3,4-dihydro-1H-quinolin-3-yl)acetaldehyde
• CAS: 726187-33-3
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: KDZAGSFZDQSOKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-哌嗪-1-噻吩并[3,2-c]吡啶 、 2-oxo-1,2,3,4-tetrahydroquinolin-3-acetaldehyde 在 titanium(IV) isopropylate 、 sodium cyanoborohydride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 24.0h， 以49%的产率得到3-[2-(4-Thieno[3,2-c]pyridin-4-yl-piperazin-1-yl)-ethyl]-3,4-dihydro-1H-quinolin-2-one
  参考文献：
  名称：

  Synthesis and SAR of 3- and 4-substituted quinolin-2-ones: discovery of mixed 5-HT1B/5-HT2A receptor antagonists

  摘要：

  Quinolin-2-ones bearing a heteroaryl-piperazine linked by a two carbon chain at the 3- or 4-position were synthesised and evaluated as mixed 5-HT1B/5-HT2A receptor antagonists. Potent mixed antagonists were obtained with thieno[3,2-c]pyridine derivatives. In this series, compound 2.1 (SL 65.0472) proved to be functional antagonist at both the 5-HT2A receptor (rat in vivo 5-HT-induced hypertension model) and the 5-HT1B receptor (dog in vitro saphenous vein assay). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00118-3
• 作为产物：
  描述：

  S-pent-4-ynyl 2-(2-oxo-3,4-dihydro-1H-quinolin-3-yl)ethanethioate 在 偶氮二异丁腈 、 苯硫酚 作用下， 以 苯 为溶剂， 反应 9.0h， 以64%的产率得到2-oxo-1,2,3,4-tetrahydroquinolin-3-acetaldehyde
  参考文献：
  名称：

  硫代马来酸酐：通过自由基加成、亲核开环和随后的硫代羧酸盐操作合成 α-取代的 γ-和 δ-内酯的方便构建块

  摘要：

  在用三（三甲基甲硅烷基）硅烷和自由基引发剂处理后，碘代烷基叔丁基碳酸酯和氨基甲酸酯与硫代马来酸酐发生干净的自由基加成，以高产率得到取代的硫代琥珀酸酐。除去叔丁氧羰基后，环化得到在α-位被硫代羧酸残基取代的内酯或内酰胺。该基团通过与缺电子磺酰胺反应转化为酰胺，或通过衍生硫酯与苯硫酚、缺电子烯丙基苯基硫醚或苯基硼酸反应转化为醛和/或酮。

  DOI：

  10.1021/jo901219k

文献信息

• Synthesis and SAR of 3- and 4-substituted quinolin-2-ones: discovery of mixed 5-HT1B/5-HT2A receptor antagonists
  作者：Gary McCort、Christian Hoornaert、Michel Aletru、Colombe Denys、Olivier Duclos、Caroline Cadilhac、Eric Guilpain、Geneviève Dellac、Philip Janiak、Anne-Marie Galzin、Monique Delahaye、Frédérique Guilbert、Stephen O'Connor

  DOI：10.1016/s0968-0896(01)00118-3

  日期：2001.8

  Quinolin-2-ones bearing a heteroaryl-piperazine linked by a two carbon chain at the 3- or 4-position were synthesised and evaluated as mixed 5-HT1B/5-HT2A receptor antagonists. Potent mixed antagonists were obtained with thieno[3,2-c]pyridine derivatives. In this series, compound 2.1 (SL 65.0472) proved to be functional antagonist at both the 5-HT2A receptor (rat in vivo 5-HT-induced hypertension model) and the 5-HT1B receptor (dog in vitro saphenous vein assay). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Thiomaleic Anhydride: A Convenient Building Block for the Synthesis of α-Substituted γ- and δ-Lactones through Free-Radical Addition, Nucleophilic Ring Opening, and Subsequent Thiocarboxylate Manipulation
  作者：David Crich、Md. Yeajur Rahaman

  DOI：10.1021/jo901219k

  日期：2009.9.4

  carbonates and carbamates undergo clean free-radical addition to thiomaleic anhydride to give substituted thiosuccinic anhydrides in high yield on treatment with tris(trimethylsilyl)silane and a radical initiator. After removal of the tert-butyloxycarbonyl group, cyclization then affords lactones or lactams substituted in the α-position by a thiocarboxylic acid residue. This group is converted to amides through

  在用三（三甲基甲硅烷基）硅烷和自由基引发剂处理后，碘代烷基叔丁基碳酸酯和氨基甲酸酯与硫代马来酸酐发生干净的自由基加成，以高产率得到取代的硫代琥珀酸酐。除去叔丁氧羰基后，环化得到在α-位被硫代羧酸残基取代的内酯或内酰胺。该基团通过与缺电子磺酰胺反应转化为酰胺，或通过衍生硫酯与苯硫酚、缺电子烯丙基苯基硫醚或苯基硼酸反应转化为醛和/或酮。