(E)-6-phenyl-1-(2-pyridyl)-3-(trifluoromethyl)hex-3-en-1,5-diyne

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-6-phenyl-1-(2-pyridyl)-3-(trifluoromethyl)hex-3-en-1,5-diyne
• 英文别名: 2-[(E)-6-phenyl-3-(trifluoromethyl)hex-3-en-1,5-diynyl]pyridine
• 化学式: C₁₈H₁₀F₃N
• 分子量: 297.279
• InChiKey: VOHNROQSPDRXIY-MHWRWJLKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• 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：
  4

反应信息

• 作为产物：
  描述：

  2-乙炔基吡啶 、 (Z)-1,1,1,2-tetrafluoro-5-phenyl-2-penten-4-yne 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以66%的产率得到
  参考文献：
  名称：

  Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5-diyne derivatives via an addition–elimination reaction

  摘要：

  Palladium(0)-catalyzed Sonogashira cross-coupling reaction of 2-fluoroalkylated (Z)-2-fluoro-1-iodoethene, which is easily prepared from commercially available polyfluorinated alcohols in facile three steps, with terminal alkynes in DMF at room temperature for 24 h took place stereospeciflcally to give the corresponding 1-fluoroalkylated (Z)-1-fluorobut-1-en-3-yne derivatives in good to excellent yield. Thus obtained fluoroalkylated 1-fluoroenynes were effectively subjected to addition elimination reaction with various alkynyllithiums at room temperature, leading to 3-fluoroalkylated hex-3-ene-1,5-diyne derivatives in good to high yields with an excellent E selectivity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.09.010

文献信息

• Highly stereoselective approach to 3-fluoroalkylated (E)-hex-3-ene-1,5-diyne derivatives via an addition–elimination reaction
  作者：Tsutomu Konno、Misato Kishi、Takashi Ishihara、Shigeyuki Yamada

  DOI：10.1016/j.jfluchem.2013.09.010

  日期：2013.12

  Palladium(0)-catalyzed Sonogashira cross-coupling reaction of 2-fluoroalkylated (Z)-2-fluoro-1-iodoethene, which is easily prepared from commercially available polyfluorinated alcohols in facile three steps, with terminal alkynes in DMF at room temperature for 24 h took place stereospeciflcally to give the corresponding 1-fluoroalkylated (Z)-1-fluorobut-1-en-3-yne derivatives in good to excellent yield. Thus obtained fluoroalkylated 1-fluoroenynes were effectively subjected to addition elimination reaction with various alkynyllithiums at room temperature, leading to 3-fluoroalkylated hex-3-ene-1,5-diyne derivatives in good to high yields with an excellent E selectivity. (C) 2013 Elsevier B.V. All rights reserved.