6,8-dichloro-3-[2-fluoro-2-(4-ethoxycarbonyl-(1Z,3E)-butadienyl)]-4-cromone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6,8-dichloro-3-[2-fluoro-2-(4-ethoxycarbonyl-(1Z,3E)-butadienyl)]-4-cromone
• 英文别名: ethyl (2E,4Z)-5-(6,8-dichloro-4-oxochromen-3-yl)-4-fluoropenta-2,4-dienoate
• 化学式: C₁₆H₁₁Cl₂FO₄
• 分子量: 357.165
• InChiKey: ADMRMEKXFBWJFN-CLQZKAIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl (E)-3-iodopropenoate 、 (E)-6,8-dichloro-3-(2-fluoro-2-trubutylstannyl)-4-chromone 在 copper(l) iodide 、 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以68%的产率得到6,8-dichloro-3-[2-fluoro-2-(4-ethoxycarbonyl-(1Z,3E)-butadienyl)]-4-cromone
  参考文献：
  名称：

  Coupling of 2-Substituted 1-Fluorovinylstannanes with Organic Halides Catalyzed by Palladium(0)/Copper(I) Iodide. A Mild and Stereospecific Method to Monofluoroolefins

  摘要：

  The palladium-catalyzed cross-coupling reactions of (E)- or (Z)-1-fluorovinylstannanes with aryl iodides and vinyl iodides provide good yields of stereoisomerically pure substituted fluoroolefins with retention of the double bond geometry. The reaction takes place with copper(I) iodide present as a cocatalyst at ambient temperature or in refluxing tetrahydrofuran and is tolerant of a variety of functional groups. Highly functionalized and stereoisomerically pure monofluorovinyl ketones also were obtained under mild conditions by the coupling of 1-fluorovinylstannanes with acid chlorides. (1)H-{(19)F} NOE NMR experiments unequivocally established the stereochemistry of the coupling products E-14 and Z-14.

  DOI：

  10.1021/jo982200n

文献信息

• Coupling of 2-Substituted 1-Fluorovinylstannanes with Organic Halides Catalyzed by Palladium(0)/Copper(I) Iodide. A Mild and Stereospecific Method to Monofluoroolefins
  作者：Chen、Keith Wilcoxen、Yun-Fei Zhu、Kyung-il Kim、James R. McCarthy

  DOI：10.1021/jo982200n

  日期：1999.5.1

  The palladium-catalyzed cross-coupling reactions of (E)- or (Z)-1-fluorovinylstannanes with aryl iodides and vinyl iodides provide good yields of stereoisomerically pure substituted fluoroolefins with retention of the double bond geometry. The reaction takes place with copper(I) iodide present as a cocatalyst at ambient temperature or in refluxing tetrahydrofuran and is tolerant of a variety of functional groups. Highly functionalized and stereoisomerically pure monofluorovinyl ketones also were obtained under mild conditions by the coupling of 1-fluorovinylstannanes with acid chlorides. (1)H-(19)F} NOE NMR experiments unequivocally established the stereochemistry of the coupling products E-14 and Z-14.