(Z)-methyl 5-(4-fluorophenyl)pent-2-en-4-ynoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-methyl 5-(4-fluorophenyl)pent-2-en-4-ynoate
• 英文别名: methyl (Z)-5-(4-fluorophenyl)pent-2-en-4-ynoate
• 化学式: C₁₂H₉FO₂
• 分子量: 204.201
• InChiKey: KOJKUUDBMLZVPV-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-methyl 5-(4-fluorophenyl)pent-2-en-4-ynoate 、 足球烯 在 三环己基膦 作用下， 以 邻二氯苯 为溶剂， 反应 6.0h， 以40%的产率得到
  参考文献：
  名称：

  化学，区域和立体选择性的三环己基膦催化[3 + 2]与[60]富勒烯的1,4-迈克尔加成反应生成的烯炔的环加成反应：环戊烯[60]富勒烯的合成及其电化学性质

  摘要：

  AbstractHerein we demonstrate a tricyclohexylphosphine‐catalyzed cycloaddition of (E)‐ or (Z)‐alkyl 5‐substituted phenylpent‐2‐en‐4‐ynoates with [60]fullerene to give cyclopentenofullerenes in good to excellent yields, through initial chemo‐ and regioselective 1,4‐addition of phosphines at the β‐carbon of the enyne substrates. The nucleophilic addition pattern of P(cHx)3 is found to be different from that of Gilman or Grignard reagents toward the studied enynes. The resulting cyclopentenofullerenes, characterized with spectrometric methods and single crystal X‐ray diffraction analysis, exhibit comparable or higher LUMO energy levels than a typical n‐type material, [6,6]‐phenyl‐C61‐butyric acid methyl ester (PCBM).magnified image

  DOI：

  10.1002/adsc.201300255
• 作为产物：
  描述：

  4-氟苯乙炔 、 (Z)-3-碘丙烯酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 反应 6.0h， 以67%的产率得到(Z)-methyl 5-(4-fluorophenyl)pent-2-en-4-ynoate
  参考文献：
  名称：

  化学，区域和立体选择性的三环己基膦催化[3 + 2]与[60]富勒烯的1,4-迈克尔加成反应生成的烯炔的环加成反应：环戊烯[60]富勒烯的合成及其电化学性质

  摘要：

  AbstractHerein we demonstrate a tricyclohexylphosphine‐catalyzed cycloaddition of (E)‐ or (Z)‐alkyl 5‐substituted phenylpent‐2‐en‐4‐ynoates with [60]fullerene to give cyclopentenofullerenes in good to excellent yields, through initial chemo‐ and regioselective 1,4‐addition of phosphines at the β‐carbon of the enyne substrates. The nucleophilic addition pattern of P(cHx)3 is found to be different from that of Gilman or Grignard reagents toward the studied enynes. The resulting cyclopentenofullerenes, characterized with spectrometric methods and single crystal X‐ray diffraction analysis, exhibit comparable or higher LUMO energy levels than a typical n‐type material, [6,6]‐phenyl‐C61‐butyric acid methyl ester (PCBM).magnified image

  DOI：

  10.1002/adsc.201300255

文献信息

• Palladium-Catalyzed Regio- and Stereoselective Hydrosulfonation of Propiolate Esters
  作者：Shih-Ching Chuang、Selvam Raju、Pratheepkumar Annamalai、Fu-Wei Chan、Po-Yen Tseng、Po-Yen Chen、Ting-Shen Kuo

  DOI：10.1055/s-0036-1588501

  日期：2017.11

  propiolate esters to yield alkenyl sulfonates is demonstrated. The formation of alkenyl sulfonates is highly regio- and stereoselective with favorable yields of up to 95%, and two of the alkenyl sulfonates are utilized for a Sonogashira cross-coupling reaction to produce (Z)-1,3-enynoates. An efficient palladium-catalyzed addition reaction of alkyl- and arylsulfonic acids to propiolate esters to yield

  摘要 证明了烷基和芳基磺酸的有效钯催化加成反应以丙酸酯化以产生烯基磺酸盐。烯基磺酸盐的形成具有很高的区域选择性和立体选择性，产率高达95％，并且其中两个烯基磺酸盐用于Sonogashira交叉偶联反应，生成（Z）-1,3-烯醇盐。 证明了烷基和芳基磺酸的有效钯催化加成反应以丙酸酯化以产生烯基磺酸盐。烯基磺酸盐的形成具有很高的区域选择性和立体选择性，产率高达95％，并且其中两个烯基磺酸盐用于Sonogashira交叉偶联反应，生成（Z）-1,3-烯醇盐。
• Chemo-, Regio- and Stereoselective Tricyclohexylphosphine-Catalyzed [3+2] Cycloaddition of Enynes with [60]Fullerene Initiated by 1,4-Michael Addition: Synthesis of Cyclopenteno[60]fullerenes and their Electrochemical Properties
  作者：Po-Yen Tseng、Shih-Ching Chuang

  DOI：10.1002/adsc.201300255

  日期：2013.8.12

  AbstractHerein we demonstrate a tricyclohexylphosphine‐catalyzed cycloaddition of (E)‐ or (Z)‐alkyl 5‐substituted phenylpent‐2‐en‐4‐ynoates with [60]fullerene to give cyclopentenofullerenes in good to excellent yields, through initial chemo‐ and regioselective 1,4‐addition of phosphines at the β‐carbon of the enyne substrates. The nucleophilic addition pattern of P(cHx)3 is found to be different from that of Gilman or Grignard reagents toward the studied enynes. The resulting cyclopentenofullerenes, characterized with spectrometric methods and single crystal X‐ray diffraction analysis, exhibit comparable or higher LUMO energy levels than a typical n‐type material, [6,6]‐phenyl‐C61‐butyric acid methyl ester (PCBM).magnified image