(1H,1H,2H,2H-perfluorooctyl) diphenylphosphinite | 201936-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1H,1H,2H,2H-perfluorooctyl) diphenylphosphinite
• 英文别名: Diphenyl(3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctoxy)phosphane
• CAS: 201936-60-9
• 化学式: C₂₀H₁₄F₁₃OP
• 分子量: 548.284
• InChiKey: OFWBXEZRZCRPAI-UHFFFAOYSA-N

物化性质

• 沸点：
  376.557±52.00 °C(Press: 760.00 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  di(rhodium)tetracarbonyl dichloride 、 (1H,1H,2H,2H-perfluorooctyl) diphenylphosphinite 以 二氯甲烷 为溶剂， 以69%的产率得到trans-[Rh(CO)(Cl)(PPh₂OCH₂CH₂(CF₂)5CF₃)2]
  参考文献：
  名称：

  Synthetic, Thermochemical, and Catalytic Studies Involving Novel R₂P(OR_f) [R = Alkyl or Aryl; R_f = CH₂CH₂(CF₂)₅CF₃] Ligands

  摘要：

  A series of mixed alkyl (or aryl) phosphinite compounds have been prepared from the alcohol CF3(CF2)(5)CH2CH2OH (RfOH) and an appropriate ClPR2 (R = ORf, Ph, Pr-i, Cy) in the presence of base. A bidentate analog, (RfO)(2)PCH2CH2P(ORf)(2), was synthesized in similar manner. The ligands react with [Rh(CO)(2)Cl](2) yielding the complexes RhCl(CO)(PR3)(2) The structure of RhCl(CO)(PPh2ORf)(2) (6) is reported. Infrared studies of the carbonyl complexes yield a relative ligand donor strength for this series. Solution calorimetry was performed on the rhodium reaction in order to quantify this donor strength scale. Both approaches lead to the same donor strength scale: PCy2ORf > (PPr2ORf)-Pr-i > PPh2ORf > P(ORf)(3). These phosphinite ligands can be used as ancillary ligation in rhodium-mediated hydrogenation. A cationic rhodium complex of the chelating ligand displays selected solubility in fluorous media and biphasic catalysis can be performed.

  DOI：

  10.1021/om980458y
• 作为产物：
  描述：

  3,3,4,4,5,5,6,6,7,7,8,8,8-十三氟-1-辛醇 、 二苯基氯化膦 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.17h， 以85%的产率得到(1H,1H,2H,2H-perfluorooctyl) diphenylphosphinite
  参考文献：
  名称：

  Phosphorus(III) ligands with fluorous ponytails

  摘要：

  我们制备了一系列含有一个或多个 C6F13 "马尾 "的磷(III)化合物，作为配体库，用于氟双相体系下的配位和催化研究。溶解性研究表明，只有具有三个或更多马尾的配体才能优先溶于全氟碳溶剂。

  DOI：

  10.1039/a704872f

文献信息

• Phosphorus(III) ligands with fluorous ponytails
  作者：Pravat Bhattacharyya、David Gudmunsen、Eric G. Hope、Ray D. W. Kemmitt、Danny R. Paige、Alison M. Stuart

  DOI：10.1039/a704872f

  日期：——

  A series of phosphorus(III) compounds incorporating one or more C6F13 ‘ponytails’ have been prepared as a pool of ligands for coordination and catalytic studies under the fluorous biphase regime. Solubility studies indicate that only ligands with three or more ponytails are preferentially soluble in perfluorocarbon solvents.

  我们制备了一系列含有一个或多个 C6F13 "马尾 "的磷(III)化合物，作为配体库，用于氟双相体系下的配位和催化研究。溶解性研究表明，只有具有三个或更多马尾的配体才能优先溶于全氟碳溶剂。
• Synthetic, Thermochemical, and Catalytic Studies Involving Novel R₂P(OR_f) [R = Alkyl or Aryl; R_f = CH₂CH₂(CF₂)₅CF₃] Ligands
  作者：Christopher M. Haar、Jinkun Huang、Steven P. Nolan、Jeffrey L. Petersen

  DOI：10.1021/om980458y

  日期：1998.11.1

  A series of mixed alkyl (or aryl) phosphinite compounds have been prepared from the alcohol CF3(CF2)(5)CH2CH2OH (RfOH) and an appropriate ClPR2 (R = ORf, Ph, Pr-i, Cy) in the presence of base. A bidentate analog, (RfO)(2)PCH2CH2P(ORf)(2), was synthesized in similar manner. The ligands react with [Rh(CO)(2)Cl](2) yielding the complexes RhCl(CO)(PR3)(2) The structure of RhCl(CO)(PPh2ORf)(2) (6) is reported. Infrared studies of the carbonyl complexes yield a relative ligand donor strength for this series. Solution calorimetry was performed on the rhodium reaction in order to quantify this donor strength scale. Both approaches lead to the same donor strength scale: PCy2ORf > (PPr2ORf)-Pr-i > PPh2ORf > P(ORf)(3). These phosphinite ligands can be used as ancillary ligation in rhodium-mediated hydrogenation. A cationic rhodium complex of the chelating ligand displays selected solubility in fluorous media and biphasic catalysis can be performed.