[5-[[2,4-Bis[(4-nitrophenoxy)carbonyloxymethyl]phenyl]carbamoyloxymethyl]-2-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl (4-nitrophenyl) carbonate | 1009315-12-1

• 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: [5-[[2,4-Bis[(4-nitrophenoxy)carbonyloxymethyl]phenyl]carbamoyloxymethyl]-2-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl (4-nitrophenyl) carbonate
• CAS: 1009315-12-1
• 化学式: C₄₆H₃₄N₆O₂₁
• 分子量: 1006.8
• InChiKey: YFILJUGMCDUAEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  73
• 可旋转键数：
  23
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  367
• 氢给体数：
  2
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  色胺 、 [5-[[2,4-Bis[(4-nitrophenoxy)carbonyloxymethyl]phenyl]carbamoyloxymethyl]-2-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl (4-nitrophenyl) carbonate 在 4 A molecular sieve 、 1-羟基苯并三唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 [3-[2-(1H-indol-3-yl)ethylcarbamoyloxymethyl]-4-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl N-[2,4-bis[2-(1H-indol-3-yl)ethylcarbamoyloxymethyl]phenyl]carbamate
  参考文献：
  名称：

  2,4-Bis(hydroxymethyl)aniline as a Building Block for Oligomers with Self-Eliminating and Multiple Release Properties

  摘要：

  Linear self-eliminating (LSE) systems are oligomers of branched self-eliminating linkers that disassemble upon a single triggering event under complete degradation of the linear backbone, accompanied by the release of side-chain bound effector molecules. Enabling a controlled and almost simultaneous release of different effectors (drugs) in defined ratios, LSE systems may gain importance for the development of novel combination therapeutics. On the basis of the well-known self-eliminating p-aminobenzyloxycarbonyl (PABC) linker, 2 4-bis(hydroxymethyl)aniline was considered a suitable branched linker for building LSE systems that degrade by 1,6- and 1,4-benzyl elimination reactions. A first LSE model system based on this linker was prepared in a simple procedure and was shown to release its effector payload efficiently after activation. In addition, elimination model compounds were synthesized to study the release behavior of LSE systems based on 2,4-bis(hydroxymethyl)aniline. It was found that chain degrading 1,6-benzyl elimination occurs much faster than the effector releasing 1,4-elimination.

  DOI：

  10.1021/jo702484z
• 作为产物：
  描述：

  [3-(hydroxymethyl)-4-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl N-[2,4-bis(hydroxymethyl)phenyl]carbamate 、 对硝基苯基氯甲酸酯 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 以52%的产率得到[5-[[2,4-Bis[(4-nitrophenoxy)carbonyloxymethyl]phenyl]carbamoyloxymethyl]-2-[(4-nitrophenyl)methoxycarbonylamino]phenyl]methyl (4-nitrophenyl) carbonate
  参考文献：
  名称：

  2,4-Bis(hydroxymethyl)aniline as a Building Block for Oligomers with Self-Eliminating and Multiple Release Properties

  摘要：

  Linear self-eliminating (LSE) systems are oligomers of branched self-eliminating linkers that disassemble upon a single triggering event under complete degradation of the linear backbone, accompanied by the release of side-chain bound effector molecules. Enabling a controlled and almost simultaneous release of different effectors (drugs) in defined ratios, LSE systems may gain importance for the development of novel combination therapeutics. On the basis of the well-known self-eliminating p-aminobenzyloxycarbonyl (PABC) linker, 2 4-bis(hydroxymethyl)aniline was considered a suitable branched linker for building LSE systems that degrade by 1,6- and 1,4-benzyl elimination reactions. A first LSE model system based on this linker was prepared in a simple procedure and was shown to release its effector payload efficiently after activation. In addition, elimination model compounds were synthesized to study the release behavior of LSE systems based on 2,4-bis(hydroxymethyl)aniline. It was found that chain degrading 1,6-benzyl elimination occurs much faster than the effector releasing 1,4-elimination.

  DOI：

  10.1021/jo702484z