4-(2-chloroethyl)quinolin-2-(1H)-one | 90097-59-9

• 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: 4-(2-chloroethyl)quinolin-2-(1H)-one
• 英文别名: 4-(2-Chloroethyl)-2(1H)-quinolinone；4-(2-Chloroethyl)quinolin-2(1H)-one；4-(2-chloroethyl)-1H-quinolin-2-one
• CAS: 90097-59-9
• 化学式: C₁₁H₁₀ClNO
• 分子量: 207.659
• InChiKey: VRHZUJMLXLZSNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  397.9±42.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2-chloroethyl)quinolin-2-(1H)-one 、 1-哌嗪-1-异喹啉 在 碳酸氢钠 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 18.0h， 以63%的产率得到4-[2-(4-isoquinolin-1-ylpiperazin-1-yl)ethyl]-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：

  4-乙酰氧基-2H,3h-吡喃-2,6-二酮 在 吡啶 、 sodium tetrahydroborate 、 氯化亚砜 、 硫酸 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 氯仿 、 溶剂黄146 为溶剂， 反应 48.0h， 生成 4-(2-chloroethyl)quinolin-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

文献信息

• MANOURY, PHILIPPE;OBITZ, DANIEL;PEYNOT, MICHEL;FROST, JOHN
  作者：MANOURY, PHILIPPE、OBITZ, DANIEL、PEYNOT, MICHEL、FROST, JOHN

  DOI：——

  日期：——
• DERIVES DE QUINOLEIN-2(1H)-ONE COMME ANTAGONISTES DE LA SEROTONINE
  申请人：Sanofi-Synthélabo

  公开号：EP0850235B1

  公开（公告）日：1999-12-01
• US4983607A
  申请人：——

  公开号：US4983607A

  公开（公告）日：1991-01-08
• US5958924A
  申请人：——

  公开号：US5958924A

  公开（公告）日：1999-09-28
• 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.