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 | 1236375-48-6

• 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: 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
• CAS: 1236375-48-6
• 化学式: C₄₇H₇₃BN₂O₁₁Si₃
• 分子量: 937.171
• InChiKey: DLWVPEAQPZQVGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.76
• 重原子数：
  64.0
• 可旋转键数：
  18.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  153.92
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  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 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以63%的产率得到2-(trimethylsilyl)ethyl 5-((((3,5-bis(hydroxymethyl)-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：

  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