1-undecyl-3-[5-(undec-10-enyl)-6-(5-benzyloxypentyl)-4-oxo-1,4-dihydro-pyrimidin-2-yl]-urea | 1000211-42-6

• 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: 1-undecyl-3-[5-(undec-10-enyl)-6-(5-benzyloxypentyl)-4-oxo-1,4-dihydro-pyrimidin-2-yl]-urea
• 英文别名: 1-dec-9-enyl-3-[6-oxo-4-(5-phenylmethoxypentyl)-5-undec-10-enyl-1H-pyrimidin-2-yl]urea
• CAS: 1000211-42-6
• 化学式: C₃₈H₆₀N₄O₃
• 分子量: 620.919
• InChiKey: VOIWMEQXVKFUSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  45
• 可旋转键数：
  28
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  91.8
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-undecyl-3-[5-(undec-10-enyl)-6-(5-benzyloxypentyl)-4-oxo-1,4-dihydro-pyrimidin-2-yl]-urea 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 以69%的产率得到
  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：

  2-amino-5-(undec-10-enyl)-6-(5-benzyloxypentyl)-1[H]-pyrimidin-4-one 、 10-decenyl isocyanate 在 吡啶 作用下， 以80%的产率得到1-undecyl-3-[5-(undec-10-enyl)-6-(5-benzyloxypentyl)-4-oxo-1,4-dihydro-pyrimidin-2-yl]-urea
  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

文献信息

• Biomimetic Design of Reversibly Unfolding Cross-Linker to Enhance Mechanical Properties of 3D Network Polymers
  作者：Aaron M. Kushner、Vahe Gabuchian、Evan G. Johnson、Zhibin Guan

  DOI：10.1021/ja0742176

  日期：2007.11.1

  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.