4-{4-[((Z)-Octadec-9-enyl)oxy]-phenylazo}-benzoyl chloride | 134766-39-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4-{4-[((Z)-Octadec-9-enyl)oxy]-phenylazo}-benzoyl chloride
• CAS: 134766-39-5
• 化学式: C₃₁H₄₃ClN₂O₂
• 分子量: 511.148
• InChiKey: MMHGHSBXLTWIFQ-VHVXEVGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  36.0
• 可旋转键数：
  20.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  51.02
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  O,O'-bis(1H,1H',2H,2H'-perfluorodecyl)-L-glutamate p-toluenesulfonate 、 4-{4-[((Z)-Octadec-9-enyl)oxy]-phenylazo}-benzoyl chloride 在 三乙胺 作用下， 以 氯仿 、 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 反应 120.0h， 生成 N-<<<<-4-<<(Z)-9-octadecenyl>oxy>phenyl>azo>phenyl>carbonyl>-O,O'-bis(1H,1H',2H,2H'-perfluorodecyl)-L-glutamate
  参考文献：
  名称：

  Self-assembly of bilayers from double-chain fluorocarbon amphiphiles in aprotic organic solvents: thermodynamic origin and generalization of the bilayer assembly

  摘要：

  We designed new fluorocarbon amphiphiles, 3-7, that undergo spontaneous bilayer formation in organic media. They are comprized of double fluorocarbon chains and a single oleyl chain as solvophobic and solovophilic moieties, respectively. These two molecular modules were linked through the chiral L-glutamate residue. When dispersed in chlorocyclohexane or benzene, these amphiphiles formed stable bilayer assemblies that gave rise to morphologies such as tubes, tapes, rods, and particles as confirmed by electron microscopy. These dispersions showed bilayer/monomer phase transitions as inferred by differential scanning calorimetry. This phase transition was accompanied by changes of the helical pitch of the fluorocarbon conformation and of intermolecular hydrogen bonding among the glutamate moiety. From the surface tension analysis of adsorbed monolayers at the air/liquid interface, we concluded that the bilayer formation in bulk chlorocyclohexane was driven by the enthalpic change. Limited miscibilities between fluorocarbon chains and hydrocarbon solvents produced the main enthalpic driving force of the molecular association, and the hydrogen bonding and van der Waals force of the aromatic moieties served as secondary driving forces. The molar fraction at CMC (critical membrane or micelle concentration), which reflects instability of aggregates, was greater than those of aqueous bilayers (below 10(-7)) but smaller than those of aqueous micelles (above 10(-4)). The chromophoric bilayers 6 (Phe-Ole) and 7 (Azo-Ole) showed large molecular ellipticities of 10(5)-10(6) deg.cm(2).dmol(-1) in their CD spectra, Molecular ordering in the novel bilayers was not inferior to those of conventional aqueous bilayers, although their bilayer stability does not surpass that of aqueous bilayers.

  DOI：

  10.1021/ja00092a008
• 作为产物：
  描述：

  4-(4-羟基-偶氮苯)苯甲酸乙酯 在 氢氧化钾 、 氯化亚砜 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 4-{4-[((Z)-Octadec-9-enyl)oxy]-phenylazo}-benzoyl chloride
  参考文献：
  名称：

  Self-assembly of bilayers from double-chain fluorocarbon amphiphiles in aprotic organic solvents: thermodynamic origin and generalization of the bilayer assembly

  摘要：

  We designed new fluorocarbon amphiphiles, 3-7, that undergo spontaneous bilayer formation in organic media. They are comprized of double fluorocarbon chains and a single oleyl chain as solvophobic and solovophilic moieties, respectively. These two molecular modules were linked through the chiral L-glutamate residue. When dispersed in chlorocyclohexane or benzene, these amphiphiles formed stable bilayer assemblies that gave rise to morphologies such as tubes, tapes, rods, and particles as confirmed by electron microscopy. These dispersions showed bilayer/monomer phase transitions as inferred by differential scanning calorimetry. This phase transition was accompanied by changes of the helical pitch of the fluorocarbon conformation and of intermolecular hydrogen bonding among the glutamate moiety. From the surface tension analysis of adsorbed monolayers at the air/liquid interface, we concluded that the bilayer formation in bulk chlorocyclohexane was driven by the enthalpic change. Limited miscibilities between fluorocarbon chains and hydrocarbon solvents produced the main enthalpic driving force of the molecular association, and the hydrogen bonding and van der Waals force of the aromatic moieties served as secondary driving forces. The molar fraction at CMC (critical membrane or micelle concentration), which reflects instability of aggregates, was greater than those of aqueous bilayers (below 10(-7)) but smaller than those of aqueous micelles (above 10(-4)). The chromophoric bilayers 6 (Phe-Ole) and 7 (Azo-Ole) showed large molecular ellipticities of 10(5)-10(6) deg.cm(2).dmol(-1) in their CD spectra, Molecular ordering in the novel bilayers was not inferior to those of conventional aqueous bilayers, although their bilayer stability does not surpass that of aqueous bilayers.

  DOI：

  10.1021/ja00092a008