2,2'-[亚丁基二[[2-(叔-丁基)-5-甲基-p-亚苯基]氧代]]二[5,5-二甲基-1,3,2-二噁磷己环] | 140137-15-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2,2'-[亚丁基二[[2-(叔-丁基)-5-甲基-p-亚苯基]氧代]]二[5,5-二甲基-1,3,2-二噁磷己环]
• 英文名称: (E)-2-fluoro-3-(2-pyridyl)acrylonitrile
• 英文别名: (E)-2-fluoro-3-pyridin-2-ylprop-2-enenitrile
• CAS: 140137-15-1
• 化学式: C₈H₅FN₂
• 分子量: 148.14
• InChiKey: SUHJVGJLQDTXKV-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  吡啶-2-甲醛 、 (diphenylphosphinoyl)fluoroacetonitrile 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 2,2'-[亚丁基二[[2-(叔-丁基)-5-甲基-p-亚苯基]氧代]]二[5,5-二甲基-1,3,2-二噁磷己环] 、 (2Z)-2-氟-3-(2-吡啶基)丙烯腈
  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

文献信息

• Xu, Ze-Qi; DesMarteau, Darryl D., Journal of the Chemical Society. Perkin transactions I, 1992, # 3, p. 313 - 316
  作者：Xu, Ze-Qi、DesMarteau, Darryl D.

  DOI：——

  日期：——
• α-Fluoroacrylonitriles: Horner–Wittig synthesis and conversion into 2-fluoroallylamines and C-(1-fluorovinyl)nitrones
  作者：Jan Hein van Steenis、Adrianus M.C.H van den Nieuwendijk、Arne van der Gen

  DOI：10.1016/j.jfluchem.2003.11.001

  日期：2004.1

  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.