氟碘乙酸甲酯 | 181224-33-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 氟碘乙酸甲酯
• 英文名称: Methyl fluoroiodoacetate
• 英文别名: Methyl 2-fluoro-2-iodoacetate
• CAS: 181224-33-9
• 化学式: C₃H₄FIO₂
• 分子量: 217.966
• InChiKey: AFMZZOZNDCSFIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  氟碘乙酸甲酯 在 烯丙基醚 、 铁粉 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以81%的产率得到
  参考文献：
  名称：

  Novel and practical preparation of α-fluoro-functionalized esters from fluoroiodoacetates

  摘要：

  The addition reaction of fluoroiodoacetates 2 to various electron-rich alkenes 3 initiated by iron powder in dry THF at 70-80 degrees C gave 1 : 1 adducts 4 in good yields. A variety of functionalities in the alkenes such as trimethylsilyl, alkoxy, acetoxy, hydroxy and ester could be tolerated under the reaction conditions. Reduction of the adducts 4 with Zn-AcOH in ethanol or Zn-NiCl2 . 6H(2)O in moist THF was readily accomplished, and the overall procedure was amenable to a convenient one-flask procedure, Treatment of fluoroiodoacetates 2 with electron-deficient alkenes 7 in the presence of an Fe-CrCl3 . 6H(2)O-bpy bimetal redox system in ethanol at 70-80 degrees C resulted in the formation of iodine-free 1 : 1 adducts 8 in moderate to good yields. It is proposed that the addition reactions of fluoroiodoacetates 2 to electron-rich and electron-deficient alkenes proceeded through a single-electron-transfer mechanism.

  DOI：

  10.1039/p19960001741
• 作为产物：
  描述：

  methyl chlorofluoroacetate 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以78%的产率得到氟碘乙酸甲酯
  参考文献：
  名称：

  Novel and practical preparation of α-fluoro-functionalized esters from fluoroiodoacetates

  摘要：

  The addition reaction of fluoroiodoacetates 2 to various electron-rich alkenes 3 initiated by iron powder in dry THF at 70-80 degrees C gave 1 : 1 adducts 4 in good yields. A variety of functionalities in the alkenes such as trimethylsilyl, alkoxy, acetoxy, hydroxy and ester could be tolerated under the reaction conditions. Reduction of the adducts 4 with Zn-AcOH in ethanol or Zn-NiCl2 . 6H(2)O in moist THF was readily accomplished, and the overall procedure was amenable to a convenient one-flask procedure, Treatment of fluoroiodoacetates 2 with electron-deficient alkenes 7 in the presence of an Fe-CrCl3 . 6H(2)O-bpy bimetal redox system in ethanol at 70-80 degrees C resulted in the formation of iodine-free 1 : 1 adducts 8 in moderate to good yields. It is proposed that the addition reactions of fluoroiodoacetates 2 to electron-rich and electron-deficient alkenes proceeded through a single-electron-transfer mechanism.

  DOI：

  10.1039/p19960001741

文献信息

• Novel and practical preparation of α-fluoro-functionalized esters from fluoroiodoacetates
  作者：Chengxin Zhi、Qing-Yun Chen

  DOI：10.1039/p19960001741

  日期：——

  The addition reaction of fluoroiodoacetates 2 to various electron-rich alkenes 3 initiated by iron powder in dry THF at 70-80 degrees C gave 1 : 1 adducts 4 in good yields. A variety of functionalities in the alkenes such as trimethylsilyl, alkoxy, acetoxy, hydroxy and ester could be tolerated under the reaction conditions. Reduction of the adducts 4 with Zn-AcOH in ethanol or Zn-NiCl2 . 6H(2)O in moist THF was readily accomplished, and the overall procedure was amenable to a convenient one-flask procedure, Treatment of fluoroiodoacetates 2 with electron-deficient alkenes 7 in the presence of an Fe-CrCl3 . 6H(2)O-bpy bimetal redox system in ethanol at 70-80 degrees C resulted in the formation of iodine-free 1 : 1 adducts 8 in moderate to good yields. It is proposed that the addition reactions of fluoroiodoacetates 2 to electron-rich and electron-deficient alkenes proceeded through a single-electron-transfer mechanism.