(Z)-ethyl 5-fluoro-2-hydroxypent-4-enoate | 1422177-62-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-ethyl 5-fluoro-2-hydroxypent-4-enoate
• 英文别名: ethyl (Z)-5-fluoro-2-hydroxypent-4-enoate
• CAS: 1422177-62-5
• 化学式: C₇H₁₁FO₃
• 分子量: 162.161
• InChiKey: HTKBQYZYCIXFRH-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-trimethyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)silane 、 乙醛酸乙酯 在 碳酸氢钠 、 Selectfluor 、 水 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以63%的产率得到(Z)-ethyl 5-fluoro-2-hydroxypent-4-enoate
  参考文献：
  名称：

  Tandem Reactions Involving 1-Silyl-3-Boryl-2-Alkenes. New Access to (Z)-1-Fluoro-1-Alkenes, Allyl Fluorides, and Diversely α-Substituted Allylboronates

  摘要：

  The reactions of 1-silyl-3-boryl-2-alkenes with various electrophilic reagents (Selecffluor, N-halosuccinimides, benzhydryl, and propargylic alcohols In the presence of a Lewis acid, N-alkoxycarbonyliminium ion) have been investigated as new routes to alpha-substituted allylboronates. Further functional transformations, including allylboration, Suzuki coupling, protodeboronation, and cycloisomerization, have been carried out to illustrate the synthetic potential of these gamma-borylallylsilanes.

  DOI：

  10.1021/ol4000263

文献信息

• Tandem Reactions Involving 1-Silyl-3-Boryl-2-Alkenes. New Access to (<i>Z</i>)-1-Fluoro-1-Alkenes, Allyl Fluorides, and Diversely α-Substituted Allylboronates
  作者：Aurélie Macé、Fabien Tripoteau、Qian Zhao、Eric Gayon、Emmanuel Vrancken、Jean-Marc Campagne、Bertrand Carboni

  DOI：10.1021/ol4000263

  日期：2013.2.15

  The reactions of 1-silyl-3-boryl-2-alkenes with various electrophilic reagents (Selecffluor, N-halosuccinimides, benzhydryl, and propargylic alcohols In the presence of a Lewis acid, N-alkoxycarbonyliminium ion) have been investigated as new routes to alpha-substituted allylboronates. Further functional transformations, including allylboration, Suzuki coupling, protodeboronation, and cycloisomerization, have been carried out to illustrate the synthetic potential of these gamma-borylallylsilanes.