2-(trimethylsilyl)ethyl 5-isocyanato-2-nitrobenzoate | 1055310-25-2

• 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: 2-(trimethylsilyl)ethyl 5-isocyanato-2-nitrobenzoate
• CAS: 1055310-25-2
• 化学式: C₁₃H₁₆N₂O₅Si
• 分子量: 308.366
• InChiKey: LWUWOGIRMVPYSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.87
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 5-isocyanato-2-nitrobenzoate 、 (3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)phenyl)methanol 在 dibutyltin(II) dilaurate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以1.03 g的产率得到2-(trimethylsilyl)ethyl 5-((((3,5-bis(((tert-butyldimethylsilyl)oxy)methyl)-4-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzyl)oxy)carbonyl)amino)-2-nitrobenzoate
  参考文献：
  名称：

  Dendritic chain reaction: Responsive release of hydrogen peroxide upon generation and enzymatic oxidation of methanol

  摘要：

  Signal amplification dramatically increases the sensitivity of diagnostic methods. Recently, we introduced a new technique for signal amplification that uses a distinctive dendritic chain reaction (DCR) to generate exponential evolution of a diagnostic signal. In this report, we demonstrate how the modular design of our DCR probe can be used to improve the detection sensitivity. We synthesized a new probe based on a methyl carbonate linkage, which has superior stability in aqueous media. Triggered release of methanol, which was oxidized by alcohol oxidase present in the solution, produced hydrogen peroxide that used as a reagent in the DCR amplification technique. The new probe exhibited higher sensitivity in detection of hydrogen peroxide than our previously reported probe. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.02.038
• 作为产物：
  描述：

  三光气 、 2-(trimethylsilyl)ethyl 5-amino-2-nitrobenzoate 以 甲苯 为溶剂， 反应 0.5h， 生成 2-(trimethylsilyl)ethyl 5-isocyanato-2-nitrobenzoate
  参考文献：
  名称：

  疏水性自消灭树枝状聚合物的酶促活化：具有可电离官能团的报告分子的作用

  摘要：

  自消散的树枝状大分子是独特结构的分子，通过在树枝状大分子核心处的一次切割而引发的链断裂，释放出多个尾部单元。尽管仅使用两个报告基团就证明了自消灭的树枝状分子的生物活化作用，但是具有更多报告者的自消灭的树状大分子的酶促活化作用却失败了。这些大的疏水性树状聚合物在水性条件下聚集，酶不能有效地引发链断裂。在这里，我们展示了一种对疏水性自消散树枝状聚合物进行酶促活化的简单解决方案。树突状平台上的报告子单元配备有可电离的官能团。与水的极性相互作用显着降低了树枝状聚合物的疏水性并防止了聚集体的形成。所以，

  DOI：

  10.1016/j.bmcl.2009.03.002

文献信息

• The pyridinone-methide elimination
  作者：Rotem Perry-Feigenbaum、Phil S. Baran、Doron Shabat

  DOI：10.1039/b915265b

  日期：——

  The quinone-methide elimination is a common, efficient methodology used in linkers designed to undergo self-fragmentation. Here, for the first time, we demonstrate this elimination in a pyridine ring system. Under physiological conditions, a compound constructed of a pyridine core, a reporter, and an enzymatic trigger underwent significantly faster 1,4-elimination than its parent compound with a benzene core. In addition, an AB2 self-immolative dendron based on a pyridine core released its two reporter units upon activation through 1,6- and 1,4 pyridinone-methide elimination reactions, again faster than the analogous benzene system. Increased aqueous solubility was observed with compounds based on pyridine relative to those based on benzene. The pyridinone-methide elimination could be applied as an alternative tool in designing self-immolative linkers for release of active target molecules in an aqueous environment.

  醌-亚甲基消除反应是一种常见且高效的方法，常用于设计能够自我碎裂的连接剂。在这里，我们首次在吡啶环体系中演示了这种消除反应。在生理条件下，由吡啶核心、报告基和酶触发剂构建的化合物，其1,4消除反应的速度显著快于其苯核心的母体化合物。此外，基于吡啶核心的AB2自毁树枝状聚合物在通过1,6和1,4吡啶酮-亚甲基消除反应激活后，释放其两个报告基，速度同样快于类似的苯体系。与基于苯的化合物相比，基于吡啶的化合物表现出更好的水溶性。吡啶酮-亚甲基消除反应可以作为设计自我毁灭连接剂的替代工具，用于在水相环境中释放活性靶向分子。
• The azaquinone-methide elimination: comparison study of 1,6- and 1,4-eliminations under physiological conditions
  作者：Rotem Erez、Doron Shabat

  DOI：10.1039/b808198k

  日期：——

  spacer-technique to develop dendritic and polymeric self-immolative molecular systems that can disassemble through a domino-like mechanism upon a stimulus event. In this report, we study the disassembly of a system that can disintegrate through para- and ortho-azaquinone-methide eliminations. The disassembly was evaluated with molecules that undergo single 1,6- or 1,4-elimination and with molecules that

  消除氮杂醌是一个强大而有效的反应，可用于拆解前药系统中的间隔基。我们和其他人已经使用间隔子技术来开发树突状和聚合的自消灭分子系统，这些系统可以在刺激事件发生时通过类似多米诺的机制进行分解。在本报告中，我们研究了可通过对位和邻位氮杂醌甲基化物消除而分解的系统的分解。用经历单个1,6-或1,4-消除的分子和经历双重1,6-和1,4-消除的分子评估拆卸。在生理条件下，1,6-消除比1,4-消除略快。这项研究揭示了前药系统的拆卸行为。