diisopropyl difluoromethanephosphonate | 681-80-1

• 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: diisopropyl difluoromethanephosphonate
• 英文别名: diisopropyl difluoromethylphosphonate；2-[difluoromethyl(propan-2-yloxy)phosphoryl]oxypropane
• CAS: 681-80-1
• 化学式: C₇H₁₅F₂O₃P
• mdl: MFCD00233605
• 分子量: 216.165
• InChiKey: LHZZAGSFNNHJKI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diisopropyl difluoromethanephosphonate 在 lithium diisopropyl amide 作用下， 反应 16.5h， 生成 tetraisopropyl 1,1-difluoropentane-1,5-bisphosphonate
  参考文献：
  名称：

  Highly Potent Bisphosphonate Ligands for Phosphoglycerate Kinase

  摘要：

  We have synthesized a series of novel analogs of 1,3-bisphospho-D-glyceric -acid, 1,3-BPG,(3) and evaluated their binding to phosphoglycerate kinase, PGK (EC 2.7.2.3). Nonscissile methane-phosphonic acids replace the two phosphate monoesters of 1,3-BPG and lead to several stable, tight-binding mimics of this intermediate species in glycolysis. Multiple fluorine substitution for hydrogen in the alpha-methylene groups of the phosphonic acid 1,3-BPG analogs markedly improves their binding to PGK as determined by NMR analysis. The best ligands bind some 50-100 times more strongly than does the substrate 3-phospho-D-glyceric acid and show a requirement for PKa3 to be generally below 6.0, while the presence of a beta-carbonyl group seems to be of secondary importance.

  DOI：

  10.1021/jm970839y
• 作为产物：
  描述：

  亚磷酸二异丙酯 在 sodium 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以95%的产率得到diisopropyl difluoromethanephosphonate
  参考文献：
  名称：

  Automated lineshape analysis of complex NMR spectra for a novel synthetic tetrafluorobisphosphonate, a potential ligand for phosphoglycerate kinase

  摘要：

  Tetraalkyl 1,1,3,3-tetrafluoro-2,2-dihydroxypropane-1,3-bisphosphonates were prepared. The complex P-31{H-1}- and F-19-NMR spectra were analyzed as [[A](2)X](2) and related systems. Modern methods of automated spectral analysis using DAISY under WIN-NMR were applied.

  DOI：

  10.1080/10426507.2015.1073281

文献信息

• Efficient Synthesis of Fluorophosphonylated Alkyles by Ring-Opening Reaction of Cyclic Sulfates
  作者：Sonia Amel Diab、Aboubacary Sene、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1021/ol801443s

  日期：2008.9.1

  Ring-opening reactions of functionalized 1,2-cyclic sulfates and oxetanes with the phosphonodifluoromethyl carbanion are reported. This approach allows an easy access to fluorinated beta-hydroxyphosphonates that are building blocks in the synthesis of acyclic nucleosides. Synthesis of precursors of nucleoside phosphorylase inhibitors from these alcohols is described.

  据报道官能化的1，2-环硫酸盐和氧杂环丁烷与膦酰基二氟甲基碳负离子的开环反应。这种方法可以轻松获得氟化的β-羟基膦酸酯，后者是无环核苷合成中的基础。描述了由这些醇合成核苷磷酸化酶抑制剂的前体。
• A difluorosulfide as a Freon-free source of phosphonodifluoromethyl carbanionIn memory of Arnaud who passed away in his 25th year.
  作者：Arnaud Henry-dit-Quesnel、Loic Toupet、Jean-Claude Pommelet、Thierry Lequeux

  DOI：10.1039/b301729j

  日期：——

  as starting chemicals. To circumvent this limitation, we report the preparation of a thioether as a new source of the lithiodifluoromethylphosphonate. This methodology avoiding the use of HCFCs involves a selective fluorination of sulfide followed by a thiaphilic addition of an organometallic reagent, which offers an alternative route to obtain phosphonodifluoromethyl carbanion. A contrasted reactivity

  由于环境保护法限制将HCFC和CFC用作起始化学品，二氟甲基膦酸酯的合成正变得越来越困难。为了规避这一限制，我们报告了硫醚的制备，作为硫代二氟甲基膦酸酯的新来源。避免使用HCFC的这种方法学涉及到硫化物的选择性氟化，然后硫代有机金属试剂的加入，这为获得膦酰二氟甲基碳负离子提供了另一种途径。还注意到由于中等作用而形成的对比的反应性，其允许向硫醚中添加包括硝基烯烃和DMF在内的多种亲电试剂。
• Synthesis and crystal structure of an iridium complex containing the novel electron-poor hybrid monoanionic ligand Ph2PCF2PO2(OiPr)
  作者：Daniel J. Sattler、Jake B. Bailey、Douglas B. Grotjahn

  DOI：10.1016/j.poly.2022.116162

  日期：2022.12

  a wide variety of ligands with almost any substituent are available. However, the vast majority of these phosphines have been relatively electron-rich. Monooxides of bisphosphines have been shown to form complexes that catalyze alkene polymerizations and hydroformylations. However, electron-poor versions of such ligands have not yet been explored. In this report, the hybrid ligand Ph2PCF2PO2(OiPr) with

  膦长期以来一直用于催化，并​​且可以使用具有几乎任何取代基的多种配体。然而，这些膦中的绝大多数都是相对富电子的。已显示双膦的一氧化物形成催化烯烃聚合和加氢甲酰化的络合物。然而，尚未探索此类配体的缺电子形式。在本报告中，合成了具有膦和膦酸酯部分的杂化配体Ph 2 PCF 2 PO 2 (O i Pr)，与缺电子CF 2基团连接。合成并表征了配体的 Cp*Ir 复合物。
• Fluorination of methanediphosphonate esters by perchloryl fluoride. Synthesis of fluoromethanediphosphonic acid and difluoromethanediphosphonic acid
  作者：Charles E. McKenna、Pei-De Shen

  DOI：10.1021/jo00335a053

  日期：1981.10
• Blackburn, G. Michael; Guo, Mao-Jun; Taylor, Steven, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 139 - 142
  作者：Blackburn, G. Michael、Guo, Mao-Jun、Taylor, Steven

  DOI：——

  日期：——

表征谱图