O,O-diethyl 3-butoxy-1,1-difluoropropylphosphonate

• 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: O,O-diethyl 3-butoxy-1,1-difluoropropylphosphonate
• 英文别名: diethyl (3-butoxy-1,1-difluoropropyl)phosphonate；1-(3-Diethoxyphosphoryl-3,3-difluoropropoxy)butane；1-(3-diethoxyphosphoryl-3,3-difluoropropoxy)butane
• 化学式: C₁₁H₂₃F₂O₄P
• 分子量: 288.272
• InChiKey: HFCHELBMSYCBPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二氟甲基膦酸二乙酯 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 12.25h， 生成 O,O-diethyl 3-butoxy-1,1-difluoropropylphosphonate
  参考文献：
  名称：

  Phosphonodifluoromethyl and Phosphonothiodifluoromethyl Radicals. Generation and Addition onto Alkenes and Alkynes

  摘要：

  Selanylated difluorornethylphosphonates and difluoromethylphosphonothioates are good precursors to phosphonodifluoromethyl and phosphonothiodifluoromethyl radicals, respectively. When generated in the presence of alkenes and a hydrogen donor, the corresponding alpha,alpha-difluorinated alkylphosphonates C, ID. or alkylphosphonothioates are produced in fair to good yields. The use of alkynes results in the formation of alpha,alpha-difluorinated allyl derivatives in useful yields. The presence of the sulfur atom in phosphono-thiodifluoromethyl radicals usually translates into higher isolated yields.

  DOI：

  10.1021/jo051511c

文献信息

• Hydrophosphonodifluoromethylation of Alkenes via Thiyl-Radical/Photoredox Catalysis
  作者：Wenhao Huang、Jingzhi Chen、Daocheng Hong、Wenxin Chen、Xu Cheng、Yuxi Tian、Guigen Li

  DOI：10.1021/acs.joc.7b02354

  日期：2018.1.19

  Visible-light-induced catalytic hydrophosphonodifluoromethylation of mono- and disubstituted alkenes using bromodifluoromethanephosphonate with a Hantzsch ester as the terminal reductant is reported. The combination of thiyl-radical catalysis with photoredox catalysis is important for achieving good chemoselectivity and high yields.

  据报道，使用溴二氟甲烷膦酸酯与汉茨tz酯作为末端还原剂，可见光诱导的单和双取代烯烃的催化氢膦二氟甲基化反应。硫代自由基催化与光氧化还原催化的结合对于实现良好的化学选择性和高产率是重要的。
• Sulfanyl- and Selanyldifluoromethylphosphonates as a Source of Phosphonodifluoromethyl Radicals and Their Addition onto Alkenes
  作者：Thierry Lequeux、Fanny Lebouc、Chrystel Lopin、Hongli Yang、Géraldine Gouhier、Serge R. Piettre

  DOI：10.1021/ol006746j

  日期：2001.1.1

  [GRAPHICS]Two different strategies are shown to produce sulfanyl and selanyldifluoromethylphosphonates, Thus, treatment of sulfanyldichloromethylphosphonates by 3HF . NEt3 in the presence of zinc bromide produces the corresponding sulfanyldifluoromethylphosphonates. In addition, lithiation of difluoromethylphosphonates followed by quenching with phenylsulfanyl chloride, phenylselanyl chloride, or diphenyl diselenide yields the corresponding sulfanyl- and selanyldifluorophosphonates. Generation of phosphonodifluoromethyl radicals from such precursors in the presence of alkenes produces the expected adducts.