3-acetoxy-2-hydroxy-5-nitrobenzaldehyde | 55477-55-9

• 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: 3-acetoxy-2-hydroxy-5-nitrobenzaldehyde
• 英文别名: 2-Hydroxy-3-acetoxy-5-nitrobenzaldehyd
• CAS: 55477-55-9
• 化学式: C₉H₇NO₆
• 分子量: 225.158
• InChiKey: KIUGVUATURIQFX-UHFFFAOYSA-N

物化性质

• 沸点：
  351.8±42.0 °C(Predicted)
• 密度：
  1.511±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  106.74
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-acetoxy-2-hydroxy-5-nitrobenzaldehyde 在 水 作用下， 以 乙醇 为溶剂， 以69%的产率得到2,3-二羟基-5-硝基苯甲醛
  参考文献：
  名称：

  Mechanophore-Linked Addition Polymers

  摘要：

  The use of mechanical energy to increase reaction rates and alter the distribution of products has gained considerable interest of late. However, the discovery of new mechanophores (i.e., mechanochemically reactive units) is currently time-consuming, expensive, low-yielding, and a process that is not easily scaled to large quantities. Here we show that mechanophore-linked addition polymers are easily prepared using bifunctional initiators with a living radical polymerization method. The mechanophore is positioned close to the center of the polymer, where ultrasound-generated forces are the largest. Since these forces are strongly dependent on molecular weight, the use of controlled polymerization enables fine-tuning of the mechanical activity so that mechanophore reactions are initiated while minimizing chain scission. The approach is illustrated first with the synthesis and investigation of a 1,2-disubstituted benzocyclobutene mechanophore that is incorporated into the center of a polymethacrylate (PMA) chain. Selected molecular weights are probed using ultrasound to illustrate that the 4 pi electrocyclic ring opening of the benzocyclobutene link is stress-induced. To demonstrate the broad applicability of this method for mechanophore screening, we also report a new spiropyran-linked PMA that undergoes an ultrasound-induced 6 pi-electron electrocyclic ring opening. The straightforward synthesis of mechanophore-linked addition polymers presented here shows considerable promise for the investigation of new mechanophores and will lead to a greater understanding of mechanochemical reactivity within polymer systems.

  DOI：

  10.1021/ja076189x
• 作为产物：
  描述：

  3-acetoxy-2-hydroxybenzaldehyde 在 硫酸 、 硝酸 、 溶剂黄146 作用下， 以61%的产率得到3-acetoxy-2-hydroxy-5-nitrobenzaldehyde
  参考文献：
  名称：

  Mechanophore-Linked Addition Polymers

  摘要：

  The use of mechanical energy to increase reaction rates and alter the distribution of products has gained considerable interest of late. However, the discovery of new mechanophores (i.e., mechanochemically reactive units) is currently time-consuming, expensive, low-yielding, and a process that is not easily scaled to large quantities. Here we show that mechanophore-linked addition polymers are easily prepared using bifunctional initiators with a living radical polymerization method. The mechanophore is positioned close to the center of the polymer, where ultrasound-generated forces are the largest. Since these forces are strongly dependent on molecular weight, the use of controlled polymerization enables fine-tuning of the mechanical activity so that mechanophore reactions are initiated while minimizing chain scission. The approach is illustrated first with the synthesis and investigation of a 1,2-disubstituted benzocyclobutene mechanophore that is incorporated into the center of a polymethacrylate (PMA) chain. Selected molecular weights are probed using ultrasound to illustrate that the 4 pi electrocyclic ring opening of the benzocyclobutene link is stress-induced. To demonstrate the broad applicability of this method for mechanophore screening, we also report a new spiropyran-linked PMA that undergoes an ultrasound-induced 6 pi-electron electrocyclic ring opening. The straightforward synthesis of mechanophore-linked addition polymers presented here shows considerable promise for the investigation of new mechanophores and will lead to a greater understanding of mechanochemical reactivity within polymer systems.

  DOI：

  10.1021/ja076189x