2-{di[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]phosphonium}benzenesulfonate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-{di[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]phosphonium}benzenesulfonate
• 英文别名: 2-bis[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]phosphanylbenzenesulfonic acid
• 化学式: C₂₆H₄₃O₃PS
• 分子量: 466.665
• InChiKey: VNWOSVUJKCZLKW-XBMHUJOKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  六氟苯 、 2-{di[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]phosphonium}benzenesulfonate 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 16.0h， 以52%的产率得到2-{di[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]phosphonium}-6-pentafluorophenylbenzenesulfonate
  参考文献：
  名称：

  钯和极性单体在钯催化下的结晶等规立构极性聚丙烯

  摘要：

  带有膦-磺酸盐配体的钯配合物已经实现了丙烯的中等等特异性均聚以及丙烯与极性单体的共聚。在配位体的磷原子的取代基的优化显示，大的烷基基团（例如薄荷基）的存在对于高分子量的聚丙烯的至关重要的生成（M瓦特≈10 4），并在该取代基的邻位上相对于磺酸根基团的分子量影响所得聚丙烯的分子量和全同规整度。统计分析表明，在邻位引入取代基相对于磺酸酯基团的位置，在链增长步骤中，相对于链端控制，有利于对映体位点控制。三元组的全同立构规整度可以增加到mm = 0.55-0.59，形成结晶极性的聚丙烯，这要归功于相应的X射线衍射图样中存在熔点和尖峰。

  DOI：

  10.1002/anie.201600819
• 作为产物：
  描述：

  chlorodimenthylphosphine 、 苯磺酸 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以63%的产率得到2-{di[(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl]phosphonium}benzenesulfonate
  参考文献：
  名称：

  Quantification of the Steric Influence of Alkylphosphine–Sulfonate Ligands on Polymerization, Leading to High-Molecular-Weight Copolymers of Ethylene and Polar Monomers

  摘要：

  A series of palladium/alkylphosphine-sulfonate catalysts were synthesized and examined in the homopolymerization of ethylene and the copolymerization of ethylene and polar monomers. Catalysts with alkylphosphine-sulfonate ligands containing sterically demanding alkyl substituents afforded (co)polymers whose molecular weight was increased by up to 2 orders of magnitude relative to polymers obtained from previously reported catalyst systems. The polymer molecular weight was found to be closely correlated to the Sterimol B5 parameter of the alkyl substituents in the alkylphosphine-sulfonate ligands. Thus, the use of bulky alkylphosphine-sulfonate ligands represents an effective and versatile method to prepare high-molecular-weight copolymers of ethylene and various polar monomers, which are difficult to obtain by previously reported methods.

  DOI：

  10.1021/ja505558e

文献信息

• Quantification of the Steric Influence of Alkylphosphine–Sulfonate Ligands on Polymerization, Leading to High-Molecular-Weight Copolymers of Ethylene and Polar Monomers
  作者：Yusuke Ota、Shingo Ito、Jun-ichi Kuroda、Yoshikuni Okumura、Kyoko Nozaki

  DOI：10.1021/ja505558e

  日期：2014.8.27

  A series of palladium/alkylphosphine-sulfonate catalysts were synthesized and examined in the homopolymerization of ethylene and the copolymerization of ethylene and polar monomers. Catalysts with alkylphosphine-sulfonate ligands containing sterically demanding alkyl substituents afforded (co)polymers whose molecular weight was increased by up to 2 orders of magnitude relative to polymers obtained from previously reported catalyst systems. The polymer molecular weight was found to be closely correlated to the Sterimol B5 parameter of the alkyl substituents in the alkylphosphine-sulfonate ligands. Thus, the use of bulky alkylphosphine-sulfonate ligands represents an effective and versatile method to prepare high-molecular-weight copolymers of ethylene and various polar monomers, which are difficult to obtain by previously reported methods.
• Crystalline Isotactic Polar Polypropylene from the Palladium‐Catalyzed Copolymerization of Propylene and Polar Monomers
  作者：Yusuke Ota、Shingo Ito、Minoru Kobayashi、Shinichi Kitade、Kazuya Sakata、Takao Tayano、Kyoko Nozaki

  DOI：10.1002/anie.201600819

  日期：2016.6.20

  Moderately isospecific homopolymerization of propylene and the copolymerization of propylene and polar monomers have been achieved with palladium complexes bearing a phosphine‐sulfonate ligand. Optimization of substituents on the phosphorus atom of the ligand revealed that the presence of bulky alkyl groups (e.g. menthyl) is crucial for the generation of high‐molecular‐weight polypropylenes (Mw≈104)

  带有膦-磺酸盐配体的钯配合物已经实现了丙烯的中等等特异性均聚以及丙烯与极性单体的共聚。在配位体的磷原子的取代基的优化显示，大的烷基基团（例如薄荷基）的存在对于高分子量的聚丙烯的至关重要的生成（M瓦特≈10 4），并在该取代基的邻位上相对于磺酸根基团的分子量影响所得聚丙烯的分子量和全同规整度。统计分析表明，在邻位引入取代基相对于磺酸酯基团的位置，在链增长步骤中，相对于链端控制，有利于对映体位点控制。三元组的全同立构规整度可以增加到mm = 0.55-0.59，形成结晶极性的聚丙烯，这要归功于相应的X射线衍射图样中存在熔点和尖峰。