diisopropyl 1,1-difluoro-5-hydroxypentylphosphonate | 792960-04-4

• 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 1,1-difluoro-5-hydroxypentylphosphonate
• 英文别名: 1,1-Difluoro-5-hydroxypentylphosphonic acid diisopropyl ester；5-di(propan-2-yloxy)phosphoryl-5,5-difluoropentan-1-ol
• CAS: 792960-04-4
• 化学式: C₁₁H₂₃F₂O₄P
• 分子量: 288.272
• InChiKey: FJDJJLDZIQJUDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  9
• 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

• 作为反应物：
  描述：

  diisopropyl 1,1-difluoro-5-hydroxypentylphosphonate 在 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 59.0h， 生成 2-((1-(5-(diisopropoxyphosphoryl)-5,5-difluoropentyl)-1H-1,2,3-triazol-4-yl)methyl)propane-1,3-diyl bis(2-methylacrylate)
  参考文献：
  名称：

  Fluorophosphonylated Monomers for Dental Applications

  摘要：

  The synthesis of acrylate derivatives bearing a difluorophosphonic acid function has been realized by ring-opening reaction of oxac-ycles and alkylation of fluorinated carbanions. Their use in self-etch adhesives is reported. The resulting adhesives based on difluorophosphonic acid monomers provide significantly higher dentin shear bond strength (SBS) than the one based on phosphonic acid, mainly due to the presence of fluorine atoms.

  DOI：

  10.1021/op500108m
• 作为产物：
  描述：

  四氢呋喃 、 diisopropyl methylsulfanyldifluoromethylphosphonate 在 叔丁基锂 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.58h， 以71%的产率得到diisopropyl 1,1-difluoro-5-hydroxypentylphosphonate
  参考文献：
  名称：

  Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition

  摘要：

  描述了从二氟磷酸硫化物出发制备含有二氟甲基磷酸酯基团和大环三唑部分的几种非核苷酸的过程。合成的关键步骤涉及二氟磷酸基团化的叠氮化合物与源自胸苷和2-氨基-6-氯嘌呤的丙炔化核苷酸之间的铜(I)催化Huisgen 1,3-偶极环加成反应。

  DOI：

  10.1039/b912724k

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。
• 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.
• Fluorophosphonylated Monomers for Dental Applications
  作者：Mathieu Derbanne、Anais Zulauf、Stéphane Le Goff、Emmanuel Pfund、Michaël Sadoun、Thi-Nhàn Pham、Thierry Lequeux

  DOI：10.1021/op500108m

  日期：2014.8.15

  The synthesis of acrylate derivatives bearing a difluorophosphonic acid function has been realized by ring-opening reaction of oxac-ycles and alkylation of fluorinated carbanions. Their use in self-etch adhesives is reported. The resulting adhesives based on difluorophosphonic acid monomers provide significantly higher dentin shear bond strength (SBS) than the one based on phosphonic acid, mainly due to the presence of fluorine atoms.
• Synthesis of fluorophosphonylated acyclic nucleotide analogues via copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition
  作者：Sonia Amel Diab、Antje Hienzch、Cyril Lebargy、Stéphane Guillarme、Emmanuel Pfund、Thierry Lequeux

  DOI：10.1039/b912724k

  日期：——

  Preparation of several acyclonucleosides containing both a difluoromethylphosphonate group and a triazole moiety is described starting from a difluorophosphonosulfide. The key step of the synthesis involves a copper(I)-catalyzed Huisgen 1-3 dipolar cycloaddition between difluorophosphonylated azides and propargylated nucleobases derived from thymine and 2-amino-6-chloropurine.

  描述了从二氟磷酸硫化物出发制备含有二氟甲基磷酸酯基团和大环三唑部分的几种非核苷酸的过程。合成的关键步骤涉及二氟磷酸基团化的叠氮化合物与源自胸苷和2-氨基-6-氯嘌呤的丙炔化核苷酸之间的铜(I)催化Huisgen 1,3-偶极环加成反应。