2-chloro-3-(4-methylphenyl)quinoline | 85274-00-6

• 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-(4-methylphenyl)quinoline
• 英文别名: 2-chloro-3-p-tolylquinoline
• CAS: 85274-00-6
• 化学式: C₁₆H₁₂ClN
• 分子量: 253.731
• InChiKey: OHNVWDNZOIYYEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-甲胺乙硫醇盐酸盐 、 2-chloro-3-(4-methylphenyl)quinoline 在 sodium hydride 作用下， 生成 2-(2-dimethylaminoethylthio)-3-p-tolylquinoline
  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：

  在 N,N-二异丙基乙胺 、 三氯氧磷 、 四丁基氯化铵 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以99%的产率得到2-chloro-3-(4-methylphenyl)quinoline
  参考文献：
  名称：

  Tetrabutylammonium chloride-triggered 6-endo cyclization of o-alkynylisocyanobenzenes: an efficient synthesis of 2-chloro-3-substituted quinolines

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2009.09.096

文献信息

• Synthesis of 2-Halogenated Quinolines by Halide-Mediated Intramolecular Cyclization of<i>o</i>-Alkynylaryl Isocyanides
  作者：Takenori Mitamura、Akihiro Nomoto、Motohiro Sonoda、Akiya Ogawa

  DOI：10.1246/bcsj.20100044

  日期：2010.7.15

  When o-alkynylaryl isocyanides 1 are treated with triethylamine in chloroform, intramolecular chlorinating cyclization of the isocyanides takes place, affording the corresponding 2-chlorinated quinoline derivatives 2 in good to excellent yields, selectively. Bromoform can be also used for the brominating cyclization of 1. Furthermore, fluorinating and iodinating cyclization of o-alkynylaryl isocyanides has been attained by the selection of fluoride and iodide (ion) sources.

  当o-烷基炔基芳基异氰酸酯1在氯仿中与三乙胺反应时，发生异氰酸酯的分子内氯化环化，选择性地生成相应的2-氯化喹啉衍生物2，产率良好到优异。溴仿也可以用于1的溴化环化。此外，通过选择氟化物和碘化物（离子）来源，实现了o-烷基炔基芳基异氰酸酯的氟化和碘化环化反应。
• Synthesis of 4-Aryl-2-aminopyridine Derivatives and Related Compounds
  作者：Vladimir Pavlovic、Milos Petkovic、Stanimir Popovic、Vladimir Savic

  DOI：10.1080/00397910902898601

  日期：2009.11.5

  Abstract A short, efficient, and high-yielding synthesis of 4-aryl-2-aminopyridine derivatives has been developed. The route employs two palladium-catalyzed processes, the Suzuki reaction and the Buchwald–Hartwig amination, as the key steps. The same approach has been used for preparation of the corresponding quinoline derivatives. In addition, a brief study of biological properties showed the anticancer

  摘要 4-芳基-2-氨基吡啶衍生物的快速、高效、高产合成已被开发。该路线采用两个钯催化过程，铃木反应和 Buchwald-Hartwig 胺化，作为关键步骤。相同的方法已用于制备相应的喹啉衍生物。此外，对生物学特性的简要研究显示了这些化合物的抗癌潜力。
• 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：——
• 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.
• Synthesis and 5-hydroxytryptamine antagonist activity of 2-[[2-(dimethylamino)ethyl]thio]-3-phenylquinoline and its analogs
  作者：Thomas P. Blackburn、Barry Cox、Allen J. Guildford、David J. Le Count、Derek N. Middlemiss、Robert J. Pearce、Craig W. Thornber

  DOI：10.1021/jm00395a013

  日期：1987.12

  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.