2-chloro-3-(thiophen-3-yl)quinoline | 85274-54-0

• 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: 2-chloro-3-(thiophen-3-yl)quinoline
• 英文别名: 2-Chloro-3-thiophen-3-ylquinoline
• CAS: 85274-54-0
• 化学式: C₁₃H₈ClNS
• 分子量: 245.732
• InChiKey: UHHAFHBOCDSOSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲胺乙硫醇盐酸盐 、 2-chloro-3-(thiophen-3-yl)quinoline 在 sodium hydride 作用下， 生成 N,N-dimethyl-2-(3-thiophen-3-ylquinolin-2-yl)sulfanylethanamine
  参考文献：
  名称：

  Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogs

  摘要：

  A series of 2-[(2-aminoethyl)thio]quinolines substituted at the 3-position with alkyl, aryl, or heteroaryl groups has been prepared in the search for novel and selective 5-HT2 antagonists. The affinity of the compounds for 5-HT1 receptor sites was measured by their ability to displace [3H]-5-HT from rat brain synaptosomes whereas the affinity for 5-HT2 receptor sites was measured by their ability to displace [3H]spiperone from synaptosomes prepared from rat brain cortex. The 5-HT2 antagonist properties of the compounds were measured in vivo by their antagonism of 5-hydroxytryptophan-induced head twitches in the mouse and by their antagonism of hyperthermia induced by fenfluramine (N-ethyl-alpha-methyl-m-(trifluoromethyl)phenethylamine hydrochloride) in the rat. The structure-activity relationships in this series are discussed and the properties of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline hydrochloride (70) are highlighted.

  DOI：

  10.1021/jm00395a013
• 作为产物：
  描述：

  3-噻吩硼酸 、 3-溴-2-氯喹啉 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以59%的产率得到2-chloro-3-(thiophen-3-yl)quinoline
  参考文献：
  名称：

  通过布朗斯台德酸介导的环异构化合成噻吩并[2,3-h]-/[3,2-h]喹啉和噻吩并[2,3-f]喹啉。

  摘要：

  几种噻吩并[2,3 - h ]-/[3,2 - h ]-和[2,3 - f ]喹啉已由2,3-二卤代吡啶或-喹啉通过位点选择性Pd催化交叉偶联合成反应和布朗斯台德酸介导的环异构化是最后的关键步骤。这种新开发的合成策略以模块化方式用于合成多种区域异构衍生物，耐受各种官能团，并以高选择性进行，并且以高总产率分离所需的最终产物。

  DOI：

  10.1039/d0ob01194k