Ethyl 4-(diethoxyphosphoryl)-4,4-difluorobutyrate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl 4-(diethoxyphosphoryl)-4,4-difluorobutyrate
• 英文别名: Ethyl 4-diethoxyphosphoryl-4,4-difluorobutanoate
• 化学式: C₁₀H₁₉F₂O₅P
• 分子量: 288.228
• InChiKey: NSOCZCZGRJNLNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  7

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 甲苯 为溶剂， 反应 2.0h， 生成 Ethyl 4-(diethoxyphosphoryl)-4,4-difluorobutyrate
  参考文献：
  名称：

  Sulfanyl- and Selanyldifluoromethylphosphonates as a Source of Phosphonodifluoromethyl Radicals and Their Addition onto Alkenes

  摘要：

  [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.

  DOI：

  10.1021/ol006746j

文献信息

• Facile syntheses of α,α-difluoro-β-ketophosphonates
  作者：Thierry P. Lequeux、Jonathan M. Percy

  DOI：10.1039/c39950002111

  日期：——

  The cerium-mediated reaction between lithio (diethyldifluoromethyl)-phosphonate 2 proceeds smoothly to afford good yields of ketophosphonates; the reaction with DMF led to the formation of the corresponding aldehyde which was isolated as a hydrate with interesting and useful properties.

  铈介导的(二乙基二氟甲基)-膦酸锂 2 反应进行顺利，可得到产率很高的酮膦酸盐；与 DMF 反应可生成相应的醛，并分离出具有有趣和有用性质的水合物。
• Nucleophilic additions of [(diethoxyphosphoryl)difluoromethyl]lithium to α,β-unsaturated compounds
  作者：Prabhakar Cherkupally、Petr Beier

  DOI：10.1016/j.jfluchem.2012.02.003

  日期：2012.5

  The presence of HMPA leads to an increase of 1,4- versus 1,2-additions of [(diethoxyphosphoryl)difluoromethyl]lithium onto alpha,beta-unsaturated ketones and provides products of conjugated addition in moderate to good yields. In the absence of HMPA, benzylidine or alkylidine 1,3-diones, malononitriles or malonates as well as nitroalkenes and other Michael acceptors give products of 1,4-addition in good to high yields. (c) 2012 Elsevier B.V. All rights reserved.
• Hu, Chang-Ming; Chen, Jian, Journal of the Chemical Society. Perkin transactions I, 1993, # 3, p. 327 - 330
  作者：Hu, Chang-Ming、Chen, Jian

  DOI：——

  日期：——
• Hu Chang-Ming, Chen Jian, J. Chem. Soc. Perkin Trans. 1, (1993) N 3, S 327-330
  作者：Hu Chang-Ming, Chen Jian

  DOI：——

  日期：——
• 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.