3-[4'-benzyloxy-3-(1H,1H,2H,2H,3H,3H-perfluorodecyl)biphenyl-4-yloxymethyl]propane-1,2-diol | 791807-64-2

• 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: 3-[4'-benzyloxy-3-(1H,1H,2H,2H,3H,3H-perfluorodecyl)biphenyl-4-yloxymethyl]propane-1,2-diol
• CAS: 791807-64-2
• 化学式: C₃₂H₂₇F₁₅O₄
• 分子量: 760.54
• InChiKey: KAKNZQISEVYSJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.36
• 重原子数：
  51.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.92
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-[4'-benzyloxy-3-(1H,1H,2H,2H,3H,3H-perfluorodecyl)biphenyl-4-yloxymethyl]propane-1,2-diol 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 36.0h， 以73.7%的产率得到3-[4'-hydroxy-3-(1H,1H,2H,2H,3H,3H-perfluorodecyl)biphenyl-4-yloxy]propane-1,2-diol
  参考文献：
  名称：

  Liquid Crystalline Bolaamphiphiles with Semiperfluorinated Lateral Chains:  Competition between Layerlike and Honeycomb-Like Organization

  摘要：

  Novel bolaamphiphilic triblockmolecules consisting of a rigid biphenyl unit, with a polar 2,3-dihydroxypropyloxy group and a phenolic OH group at opposite ends, as well as a semiperfluorinated chain in a lateral position have been synthesized via palladium catalyzed cross coupling reactions as the key steps. The thermotropic liquid crystalline behavior of these compounds was investigated by polarized light microscopy, DSC and X-ray scattering, and the influence of the length of the lateral chain on the mesomorphic properties was studied. The compound with the shortest chain as well as the long chain derivatives form lamellar mesophases composed of segregated layers of the bolaamphiphilic moieties and sublayers comprising the fluid lateral chains. The layers within the lamellar phases of the short chain compound adopt a positional correlation, leading to a 2D lattice (Col(r)/p2mm), whereas the layers of the lamellar phases of the long chain derivatives are noncorrelated (Lam). Compounds with a medium chain length organize into columnar phases, where the nonpolar lateral chains segregate into columns, which are embedded in networks of regular (Col(h)) or stretched (Col(r)/c2mm) hexagonal cylinder shells consisting of the bolaamphiphilic units. In total, an unusual phase sequence was found, where, with respect to the chain length, columnar mesophases occur between two mesophases with layer organization.

  DOI：

  10.1021/ja048224v
• 作为产物：
  描述：

  4-[4-bromo-2-(1H,1H,2H,2H,3H,3H-perfluorodecyl)phenoxymethyl]-2,2-dimethyl-1,3-dioxolane 在 盐酸 、 四(三苯基膦)钯 、 碳酸氢钠 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 9.0h， 生成 3-[4'-benzyloxy-3-(1H,1H,2H,2H,3H,3H-perfluorodecyl)biphenyl-4-yloxymethyl]propane-1,2-diol
  参考文献：
  名称：

  Liquid Crystalline Bolaamphiphiles with Semiperfluorinated Lateral Chains:  Competition between Layerlike and Honeycomb-Like Organization

  摘要：

  Novel bolaamphiphilic triblockmolecules consisting of a rigid biphenyl unit, with a polar 2,3-dihydroxypropyloxy group and a phenolic OH group at opposite ends, as well as a semiperfluorinated chain in a lateral position have been synthesized via palladium catalyzed cross coupling reactions as the key steps. The thermotropic liquid crystalline behavior of these compounds was investigated by polarized light microscopy, DSC and X-ray scattering, and the influence of the length of the lateral chain on the mesomorphic properties was studied. The compound with the shortest chain as well as the long chain derivatives form lamellar mesophases composed of segregated layers of the bolaamphiphilic moieties and sublayers comprising the fluid lateral chains. The layers within the lamellar phases of the short chain compound adopt a positional correlation, leading to a 2D lattice (Col(r)/p2mm), whereas the layers of the lamellar phases of the long chain derivatives are noncorrelated (Lam). Compounds with a medium chain length organize into columnar phases, where the nonpolar lateral chains segregate into columns, which are embedded in networks of regular (Col(h)) or stretched (Col(r)/c2mm) hexagonal cylinder shells consisting of the bolaamphiphilic units. In total, an unusual phase sequence was found, where, with respect to the chain length, columnar mesophases occur between two mesophases with layer organization.

  DOI：

  10.1021/ja048224v