4-hexylurea-benzo-18-crown-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hexylurea-benzo-18-crown-6
• 英文别名: 1-(2,5,8,11,14,17-Hexaoxabicyclo[16.4.0]docosa-1(18),19,21-trien-20-yl)-3-hexylurea；1-(2,5,8,11,14,17-hexaoxabicyclo[16.4.0]docosa-1(18),19,21-trien-20-yl)-3-hexylurea
• 化学式: C₂₃H₃₈N₂O₇
• 分子量: 454.564
• InChiKey: KAXWCJAZXUKNEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  96.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  异氰酸己酯 、 (苯并-18-冠-6)-4′-基胺 以 乙腈 为溶剂， 反应 5.0h， 以88%的产率得到4-hexylurea-benzo-18-crown-6
  参考文献：
  名称：

  Columnar Self-Assembled Ureido Crown Ethers:  An Example of Ion-Channel Organization in Lipid Bilayers

  摘要：

  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.

  DOI：

  10.1021/ja061861w

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.