2,6-二氯-3-苯基喹啉 | 85274-46-0

• 物质功能分类: 医药中间体 - 喹啉类化合物
• 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
• 中文名称: 2,6-二氯-3-苯基喹啉
• 英文名称: 2,6-dichloro-3-phenylquinoline
• CAS: 85274-46-0
• 化学式: C₁₅H₉Cl₂N
• 分子量: 274.149
• InChiKey: ZRMJWKXIYQQCAN-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C
• 沸点：
  385.3±37.0 °C(Predicted)
• 密度：
  1.331±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  18
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-甲胺乙硫醇盐酸盐 、 2,6-二氯-3-苯基喹啉 在 sodium hydride 作用下， 生成 2-(6-chloro-3-phenylquinolin-2-yl)sulfanyl-N,N-dimethylethanamine
  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：

  6-氯-3-苯基-2-喹啉醇 在 三氯氧磷 作用下， 反应 2.0h， 以75%的产率得到2,6-二氯-3-苯基喹啉
  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

文献信息

• Quinoline derivatives which are 5-hydroxytryptamine antagonists
  申请人：Imperial Chemical Industries PLC

  公开号：US04435405A1

  公开（公告）日：1984-03-06

  Compounds of the formula: ##STR1## wherein A stands for the radical --(CH.sub.2).sub.2 -- which may bear one or two defined substituents; R.sup.1 stands for a (3-4C) alkyl or cyclopropyl radical, or a phenyl radical which may optionally bear one or two defined substituents, or a heteroaryl radical of five or six ring atoms which may optionally bear a (1-3C)alkyl substituent; R.sup.2 and R.sup.3 stand for hydrogen or a (1-2C)alkyl radical, or R.sup.2 stands for a (2-4C)alkylene radical which is linked to one of the carbon atoms forming the two-carbon-atom-backbone of A so as to form, together with the adjacent nitrogen atom, a pyrrolidinyl or piperidyl radical; and one of R.sup.4 and R.sup.5 stands for hydrogen, and the other stands for hydrogen, a halogen atom or a (1-3C)alkyl or (1-3C)alkoxy radical; and acid-addition salts thereof. Processes for the manufacture of said compounds. Pharmaceutical compositions comprising one of said compounds and a pharmaceutical diluent or carrier. The compounds are 5-hydroxytryptamine antagonists.

  化合物的化学式为：##STR1## 其中A代表基团--(CH.sub.2).sub.2 --，它可以带有一个或两个定义的取代基；R.sup.1代表一个(3-4C)烷基或环丙基基团，或一个苯基，它可以选择性地带有一个或两个定义的取代基，或一个由五个或六个环原子组成的杂环基团，它可以选择性地带有一个(1-3C)烷基取代基；R.sup.2和R.sup.3代表氢或(1-2C)烷基基团，或R.sup.2代表一个(2-4C)烷基基团，它与A的两个碳原子骨架中的一个形成连接，以便与相邻的氮原子一起形成吡咯烷基或哌嗪基团；R.sup.4和R.sup.5中的一个代表氢，另一个代表氢、卤素原子或(1-3C)烷基或(1-3C)烷氧基；以及它们的酸加成盐。制造这些化合物的方法。包含其中一种化合物和药物稀释剂或载体的制药组合物。这些化合物是5-羟色胺拮抗剂。
• Tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes: an efficient synthesis of 2-chloro-3-substituted quinolines
  作者：Lanying Liu、Yong Wang、Honggen Wang、Changlan Peng、Jiaji Zhao、Qiang Zhu

  DOI：10.1016/j.tetlet.2009.09.096

  日期：2009.12

  A highly efficient one-pot synthesis of 2-chloro-3-substituted quinolines has been developed by tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes, which are generated in situ by dehydration of the corresponding N-(2-ethynylphenyl)formamides. (C) 2009 Elsevier Ltd. All rights reserved.
• Quinoline derivatives
  申请人：IMPERIAL CHEMICAL INDUSTRIES PLC

  公开号：EP0066993B1

  公开（公告）日：1985-01-30
• BLACKBURN, THOMAS P.;COX, BARRY;GUILDFORD, ALLEN J.;LE, COUNT DAVID J.;MI+, J. MED. CHEM., 30,(1987) N 12, 2252-2259
  作者：BLACKBURN, THOMAS P.、COX, BARRY、GUILDFORD, ALLEN J.、LE, COUNT DAVID J.、MI+

  DOI：——

  日期：——
• US4435405A
  申请人：——

  公开号：US4435405A

  公开（公告）日：1984-03-06