(diphenylphosphinoyl)fluoroacetonitrile | 745812-08-2

• 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: (diphenylphosphinoyl)fluoroacetonitrile
• 英文别名: 2-Diphenylphosphoryl-2-fluoroacetonitrile
• CAS: 745812-08-2
• 化学式: C₁₄H₁₁FNOP
• 分子量: 259.22
• InChiKey: JFSCCUOLYXNIEE-UHFFFAOYSA-N

物化性质

• 沸点：
  358.8±32.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  环十二酮 、 (diphenylphosphinoyl)fluoroacetonitrile 以 四氢呋喃 为溶剂， 反应 1.0h， 以62%的产率得到cyclododecylidenefluoroacetonitrile
  参考文献：
  名称：

  α-Fluoroacrylonitriles: Horner–Wittig synthesis and conversion into 2-fluoroallylamines and C-(1-fluorovinyl)nitrones

  摘要：

  alpha-Fluoroacrylonitriles 2 were synthesized in moderate to good yields by Homer-Wittig (HW) reaction of aldehydes and ketones with (diphenylphosphinoyl)fluoroacetonitrile (1), prepared in situ from commercially available fluoroacetonitrile and diphenylphosphinyl chloride. New synthetic applications of 2 are presented with the one-pot conversion into 2-fluoroallylamines 6 and C-(1-fluorovinyl)nitrones 8 through a diisobutylaluminum hydride (DIBALH)-reduction transimination protocol. The scope and limitations of this procedure are discussed. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.11.001
• 作为产物：
  描述：

  氟乙腈 、 二苯基次膦酰氯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 生成 (diphenylphosphinoyl)fluoroacetonitrile
  参考文献：
  名称：

  α-Fluoroacrylonitriles: Horner–Wittig synthesis and conversion into 2-fluoroallylamines and C-(1-fluorovinyl)nitrones

  摘要：

  alpha-Fluoroacrylonitriles 2 were synthesized in moderate to good yields by Homer-Wittig (HW) reaction of aldehydes and ketones with (diphenylphosphinoyl)fluoroacetonitrile (1), prepared in situ from commercially available fluoroacetonitrile and diphenylphosphinyl chloride. New synthetic applications of 2 are presented with the one-pot conversion into 2-fluoroallylamines 6 and C-(1-fluorovinyl)nitrones 8 through a diisobutylaluminum hydride (DIBALH)-reduction transimination protocol. The scope and limitations of this procedure are discussed. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2003.11.001