4-hexylurea-benzo-15-crown-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hexylurea-benzo-15-crown-5
• 英文别名: 1-(benzo-15-crown-5-15-yl)-3-hexylurea；hexylbenzoureido-15-crown-5-ether；1-Hexyl-3-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)urea；1-hexyl-3-(2,5,8,11,14-pentaoxabicyclo[13.4.0]nonadeca-1(15),16,18-trien-17-yl)urea
• 化学式: C₂₁H₃₄N₂O₆
• 分子量: 410.511
• InChiKey: VEHHMSUUUNLVAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  87.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4'-氨基苯并-15-冠-5-醚 、 异氰酸己酯 以 氯仿 为溶剂， 生成 4-hexylurea-benzo-15-crown-5
  参考文献：
  名称：

  跨膜Na +载体或K +通道的结构驱动选择

  摘要：

  自组装的烷基脲基苯并15冠5醚是K +阳离子的选择性离子载体，比Na +阳离子优先。传输机理是由冠醚孔和阳离子直径之间的最佳配位关系而非经典的尺寸相容性决定的。在本文中，我们证明了结构的系统变化会导致阳离子转运活性发生意想不到的修饰，并且足以产生适应性选择。我们表明，对性能的主要贡献来自对构象自由度的最佳约束，这由结合大环，氢键基团的性质和疏水尾部决定。对灵活的15冠5醚的简单更改会导致Na的选择性载体+。通过脂质和可变的疏水尾之间的相互作用，使通道疏水稳定似乎是增加活性的重要原因。相反，当受约束的氢键大环继电器在孔隙上部结构中动力较弱时，可实现受限的移位。

  DOI：

  10.1002/anie.201802570

文献信息

• Columnar Self-Assembled Ureido Crown Ethers:  An Example of Ion-Channel Organization in Lipid Bilayers
  作者：Adinela Cazacu、Christine Tong、Arie van der Lee、Thomas M. Fyles、Mihail Barboiu

  DOI：10.1021/ja061861w

  日期：2006.7.1

  The self-assembly of ureido crown-ether derivatives has been examined in homogeneous solution, in the solid state, and in planar bilayer membranes. The self-assembly is driven by head-to-tail hydrogen bonding between the urea functional groups. Dimers and higher oligomers are formed in CDCl3 solution as assessed by the change in the ureido NH chemical shift as a function of concentration. Single-crystal X-ray diffraction shows that an antiparallel association of the ureas produces columnar channels composed of face-to-face crown ethers. Powder X-ray diffraction studies also show the presence of a minor phase based upon a parallel urea association leading to an alternative columnar arrangement of the crown ethers. In bilayer membranes at low concentration of ureido crown ether added, membrane disruption is observed together with rare single-channel openings, but at higher concentration, a rich array of interconverting channel conductance states is observed. The channel results are interpreted as arising from discreet stacks of ureido crown ethers where the transport of cations would occur via the macrocycles, admixed with larger pores formed by association of the crown ether headgroups around a central large pore.