3-(2-chloroethyl)-1-methyl-3,4-dihydroquinolin-2(1H)-one | 726187-18-4

• 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: 3-(2-chloroethyl)-1-methyl-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 3-(2-Chloroethyl)-1-methyl-3,4-dihydroquinolin-2-one
• CAS: 726187-18-4
• 化学式: C₁₂H₁₄ClNO
• 分子量: 223.702
• InChiKey: NBHZEYNDSSYBQG-UHFFFAOYSA-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：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-哌嗪-1-噻吩并[3,2-c]吡啶 、 3-(2-chloroethyl)-1-methyl-3,4-dihydroquinolin-2(1H)-one 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以64%的产率得到1-Methyl-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：

  3-(2-hydroxyethyl)-3,4-dihydroquinolin-2(1H)-one 在 咪唑 、 氯化亚砜 、 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 3-(2-chloroethyl)-1-methyl-3,4-dihydroquinolin-2(1H)-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