4-chloro-2-(4-methoxyphenyl)-3-(phenylethynyl)quinoline | 1251546-31-2

• 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-chloro-2-(4-methoxyphenyl)-3-(phenylethynyl)quinoline
• 英文别名: 4-Chloro-2-(4-methoxyphenyl)-3-(2-phenylethynyl)quinoline
• CAS: 1251546-31-2
• 化学式: C₂₄H₁₆ClNO
• 分子量: 369.85
• InChiKey: CYQGOXNBBOPSIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-chloro-2-(4-methoxyphenyl)-3-(phenylethynyl)quinoline 、 甲胺 以 乙醇 为溶剂， 反应 18.0h， 以58%的产率得到2-(4-methoxyphenyl)-4-methylamino-3-(phenylethynyl)quinoline
  参考文献：
  名称：

  Regioselective alkynylation of 2-aryl-4-chloro-3-iodoquinolines and subsequent arylation or amination of the 2-aryl-3-(alkynyl)-4-chloroquinolines

  摘要：

  Palladium-CuI catalyzed Sonogashira coupling of 2-aryl-4-chloro-3-iodoquinolines with terminal acetylenes (1 equiv) in triethylamine afforded the 2-aryl-3-(alkynyl)-4-chloroquinolines as sole products. The 2-aryl-4-chloro-3-iodoquinolines coupled with excess terminal acetylenes (2.5 equiv) in dioxane/water to yield the 2-aryl-3,4-bis(alkynyl)quinoline derivatives in a one-pot operation. The 2-aryl-3-(alkynyl)-4-chloroquinolines were, in turn, subjected to arylation via Suzuki cross-coupling with arylboronic acid derivatives or amination with methylamine, respectively. The structures of the products of successive Sonogashira and Suzuki cross-couplings were also confirmed by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.043
• 作为产物：
  描述：

  4-chloro-3-iodo-2-(4'-methoxyphenyl)quinoline 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 2.0h， 以70%的产率得到4-chloro-2-(4-methoxyphenyl)-3-(phenylethynyl)quinoline
  参考文献：
  名称：

  Regioselective alkynylation of 2-aryl-4-chloro-3-iodoquinolines and subsequent arylation or amination of the 2-aryl-3-(alkynyl)-4-chloroquinolines

  摘要：

  Palladium-CuI catalyzed Sonogashira coupling of 2-aryl-4-chloro-3-iodoquinolines with terminal acetylenes (1 equiv) in triethylamine afforded the 2-aryl-3-(alkynyl)-4-chloroquinolines as sole products. The 2-aryl-4-chloro-3-iodoquinolines coupled with excess terminal acetylenes (2.5 equiv) in dioxane/water to yield the 2-aryl-3,4-bis(alkynyl)quinoline derivatives in a one-pot operation. The 2-aryl-3-(alkynyl)-4-chloroquinolines were, in turn, subjected to arylation via Suzuki cross-coupling with arylboronic acid derivatives or amination with methylamine, respectively. The structures of the products of successive Sonogashira and Suzuki cross-couplings were also confirmed by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.043