diethyl 1,1-difluoro-3-hydroxybutylphosphonate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 1,1-difluoro-3-hydroxybutylphosphonate
• 英文别名: 4-Diethoxyphosphoryl-4,4-difluorobutan-2-ol
• 化学式: C₈H₁₇F₂O₄P
• 分子量: 246.191
• InChiKey: MCUOLJDFDGCKAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二氟甲基膦酸二乙酯 、 methyloxirane 在 lithium diisopropyl amide 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以62%的产率得到diethyl 1,1-difluoro-3-hydroxybutylphosphonate
  参考文献：
  名称：

  TiCl4 and Grignard reagent-promoted ring-opening reactions of various epoxides: synthesis of γ-hydroxy-α,α-difluoromethylenephosphonates

  摘要：

  A straightforward methodology for the synthesis of diethyl gamma-hydroxy-alpha,alpha-difluoromethylenephosphonates is reported. In the presence of titanium tetrachloride, epoxide ring-opening reactions occurred upon treatment with lithium diethyl difluoromethylenephosphonate. When diethyl 3,4-epoxy-1,1-difluorobutylphosphonate was reacted with TiCl4 and Grignard reagents, the corresponding halohydrins were obtained in very good yields. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.07.146

文献信息

• Syntheses of ω-Hydroxy-α,α-difluoromethylphosphonates by Oxacycle Ring-Opening Reactions
  作者：Paul Ozouf、Grégory Binot、Jean-Claude Pommelet、Thierry P. Lequeux

  DOI：10.1021/ol048549g

  日期：2004.10.1

  Oxacycle ring-opening reactions from a non-HCFC-based source of phosphonodifluoromethyl carbanion 1 are reported. This straightforward strategy opens access to a variety of primary and secondary omega-hydroxy-alpha,alpha-difluoromethylphosphonates via one step. The syntheses of a glycerol monophosphate analogue and precursors to nucleoside phosphorylase inhibitors are described using this method.
• TiCl4 and Grignard reagent-promoted ring-opening reactions of various epoxides: synthesis of γ-hydroxy-α,α-difluoromethylenephosphonates
  作者：Romana Pajkert、Alexander A. Kolomeitsev、Magdalena Milewska、Gerd-Volker Röschenthaler、Henryk Koroniak

  DOI：10.1016/j.tetlet.2008.07.146

  日期：2008.10

  A straightforward methodology for the synthesis of diethyl gamma-hydroxy-alpha,alpha-difluoromethylenephosphonates is reported. In the presence of titanium tetrachloride, epoxide ring-opening reactions occurred upon treatment with lithium diethyl difluoromethylenephosphonate. When diethyl 3,4-epoxy-1,1-difluorobutylphosphonate was reacted with TiCl4 and Grignard reagents, the corresponding halohydrins were obtained in very good yields. (C) 2008 Published by Elsevier Ltd.