2,2,2-trichloroethyl N-[(Z)-5-fluoro-2-methylnon-4-en-3-yl]carbamate | 1187942-72-8

• 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
• 英文名称: 2,2,2-trichloroethyl N-[(Z)-5-fluoro-2-methylnon-4-en-3-yl]carbamate
• CAS: 1187942-72-8
• 化学式: C₁₃H₂₁Cl₃FNO₂
• 分子量: 348.673
• InChiKey: WDAIWEUUNCNPIR-YFHOEESVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,2,2-trichloroethyl 2-methylnon-4-yn-3-ylcarbamate 在 silver tetrafluoroborate 、 1,3-双(2,6-二-异丙基苯基)咪唑-2-亚基金(I)氯化物 、 N,N-dimethylphenylammonium trifluoromethanesulfonate 、 potassium hydrogensulfate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 反应 15.08h， 以74%的产率得到2,2,2-trichloroethyl N-[(Z)-5-fluoro-2-methylnon-4-en-3-yl]carbamate
  参考文献：
  名称：

  Regio- and Stereoselective Synthesis of Fluoroalkenes by Directed Au(I) Catalysis

  摘要：

  Au-catalyzed hydrofluorination reactions of a range of functionalized alkynes are reported. In the presence of an appropriate directing group, localized with particular spacing from the pendant alkyne, regioselective and predictable conversion of the alkyne to the Z-vinyl fluoride may be achieved, In selected cases, yields and selectivities are excellent. Additional experiments with two directing groups installed have established some initial principles with respect to a hierarchy of directing groups and their capacity for influencing hydrofluorination regioselectivity.

  DOI：

  10.1021/ol9016782