(1,4-dioxaspiro[4,5]dec-8-ylidene)fluoroacetonitrile | 745812-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1,4-dioxaspiro[4,5]dec-8-ylidene)fluoroacetonitrile
• 英文别名: 2-(1,4-dioxaspiro[4.5]decan-8-ylidene)-2-fluoroacetonitrile
• CAS: 745812-19-5
• 化学式: C₁₀H₁₂FNO₂
• 分子量: 197.209
• InChiKey: UAXWRZBOKXMIJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  42.25
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1,4-dioxaspiro[4,5]dec-8-ylidene)fluoroacetonitrile 在 sodium tetrahydroborate 、 二异丁基氢化铝 作用下， 以 甲醇 、 乙醚 、 正己烷 为溶剂， 反应 5.5h， 生成 [2-(1,4-dioxaspiro[4,5]dec-8-ylidene)-2-fluoroethyl]-p-methoxybenzylamine
  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：

  1,4-环己二酮单乙二醇缩酮 、 (diphenylphosphinoyl)fluoroacetonitrile 以 四氢呋喃 为溶剂， 反应 1.0h， 以76%的产率得到(1,4-dioxaspiro[4,5]dec-8-ylidene)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