(26E,50Z)-54,56-bis(5-hydroxypentyl)-2,4,26,28,30,52,53,55-octaazatricyclo[48.2.2.224,27]hexapentaconta-1(52),24(56),26,50(54)-tetraene-3,25,29,51-tetraone | 1000211-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (26E,50Z)-54,56-bis(5-hydroxypentyl)-2,4,26,28,30,52,53,55-octaazatricyclo[48.2.2.224,27]hexapentaconta-1(52),24(56),26,50(54)-tetraene-3,25,29,51-tetraone
• CAS: 1000211-40-4
• 化学式: C₅₈H₁₀₄N₈O₆
• 分子量: 1009.51
• InChiKey: HQTOMAKMUCRCSN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.57
• 重原子数：
  72.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  214.22
• 氢给体数：
  8.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (26E,50Z)-54,56-bis(5-hydroxypentyl)-2,4,26,28,30,52,53,55-octaazatricyclo[48.2.2.224,27]hexapentaconta-1(52),24(56),26,50(54)-tetraene-3,25,29,51-tetraone 、 甲基丙烯酸异氰基乙酯 在 di-butyltin dilaurate 作用下， 以 氯仿 为溶剂， 反应 12.0h， 以89%的产率得到2-[5-[51-[5-[2-(2-Methylprop-2-enoyloxy)ethylcarbamoyloxy]pentyl]-3,29,54,56-tetraoxo-2,4,26,28,30,52,53,55-octazatricyclo[48.2.2.224,27]hexapentaconta-1(52),24,26,50-tetraen-25-yl]pentoxycarbonylamino]ethyl 2-methylprop-2-enoate
  参考文献：
  名称：

  Biomimetic Design of Reversibly Unfolding Cross-Linker to Enhance Mechanical Properties of 3D Network Polymers

  摘要：

  We report here a biomimetic design of a reversibly unfolding modular cross-linker to enhance mechanical properties of 3D network polymers. The inspiration comes from the modular biopolymers observed in nature. A cyclic modular cross-linker based on the quadruple hydrogen bonding 4-ureido-2-pyrimidone (UPy) motif was synthesized via multistep organic synthesis. The modular crosslinker was incorporated into poly(n -butyl acrylate) by free radical polymerization. Stress-strain measurements show that the samples containing our modular cross-linker exhibit significantly enhanced mechanical properties over the control samples. Most strikingly, with increasing cross-linker density, both modulus and tensile strength are significantly improved without sacrificing extensibility. The enhanced tensile properties are attributed to the increased energy dissipating ability of the reversibly unfolding cross-linker. This introduces a novel biomimetic concept to enhance network mechanical properties through design of molecularly engineered cross-linkers.

  DOI：

  10.1021/ja0742176
• 作为产物：
  描述：

  在 palladium dihydroxide 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以73%的产率得到(26E,50Z)-54,56-bis(5-hydroxypentyl)-2,4,26,28,30,52,53,55-octaazatricyclo[48.2.2.224,27]hexapentaconta-1(52),24(56),26,50(54)-tetraene-3,25,29,51-tetraone
  参考文献：
  名称：

  Biomimetic Design of Reversibly Unfolding Cross-Linker to Enhance Mechanical Properties of 3D Network Polymers

  摘要：

  We report here a biomimetic design of a reversibly unfolding modular cross-linker to enhance mechanical properties of 3D network polymers. The inspiration comes from the modular biopolymers observed in nature. A cyclic modular cross-linker based on the quadruple hydrogen bonding 4-ureido-2-pyrimidone (UPy) motif was synthesized via multistep organic synthesis. The modular crosslinker was incorporated into poly(n -butyl acrylate) by free radical polymerization. Stress-strain measurements show that the samples containing our modular cross-linker exhibit significantly enhanced mechanical properties over the control samples. Most strikingly, with increasing cross-linker density, both modulus and tensile strength are significantly improved without sacrificing extensibility. The enhanced tensile properties are attributed to the increased energy dissipating ability of the reversibly unfolding cross-linker. This introduces a novel biomimetic concept to enhance network mechanical properties through design of molecularly engineered cross-linkers.

  DOI：

  10.1021/ja0742176