2-acryloxymethyl-6-hydroxymethyl-nitrobenzene | 1392043-93-4

• 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-acryloxymethyl-6-hydroxymethyl-nitrobenzene
• CAS: 1392043-93-4
• 化学式: C₁₁H₁₁NO₅
• 分子量: 237.212
• InChiKey: JKMAMHYAEWUIIU-UHFFFAOYSA-N

物化性质

• 沸点：
  373.6±32.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  89.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 2-acryloxymethyl-6-hydroxymethyl-nitrobenzene 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以86%的产率得到4-(3-(acryloyloxymethyl)-2-nitrobenzyloxy)-4-oxobutanoic acid
  参考文献：
  名称：

  Photodegradable Macromers and Hydrogels for Live Cell Encapsulation and Release

  摘要：

  Hydrogel scaffolds are commonly used as 3D carriers for cells because their properties can be tailored to match natural extracellular matrix. Hydrogels may be used in tissue engineering and regenerative medicine to deliver therapeutic cells to injured or diseased tissue through controlled degradation. Hydrolysis and enzymolysis are the two most common mechanisms employed for hydrogel degradation, but neither allows sequential or staged release of cells. In contrast, photodegradation allows external real-time spatial and temporal control over hydrogel degradation, and allows for staged and sequential release of cells. We synthesized and characterized a series of macromers incorporating photodegradbale ortho-nitrobenzyl (o-NB) groups in the macromer backbone. We formed hydrogels from these macromers via redox polymerization and quantified the apparent rate constants of degradation (k(app)) of each via photorheology at 370 nm, 10 mW/cm(2). Decreasing the number of aryl ethers on the o-NB group increases k(app), and changing the functionality from primary to seconday at the benzylic site dramatically increases k(app). Human mesenchymal stem cells (hMSCs) survive encapsulation in the hydrogels (90% viability postencapsulation). By exploiting the differences in reactivity of two different o-NB linkers, we quantitatively demonstrate the biased release of one stem cell population (green-fluoroescent protein expressing hMSCs) over another (red-fluorescent protein expressing hMSCs).

  DOI：

  10.1021/ja305280w
• 作为产物：
  描述：

  2-硝基间苯二甲酸 在 硼烷四氢呋喃络合物 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 49.0h， 生成 2-acryloxymethyl-6-hydroxymethyl-nitrobenzene
  参考文献：
  名称：

  Photodegradable Macromers and Hydrogels for Live Cell Encapsulation and Release

  摘要：

  Hydrogel scaffolds are commonly used as 3D carriers for cells because their properties can be tailored to match natural extracellular matrix. Hydrogels may be used in tissue engineering and regenerative medicine to deliver therapeutic cells to injured or diseased tissue through controlled degradation. Hydrolysis and enzymolysis are the two most common mechanisms employed for hydrogel degradation, but neither allows sequential or staged release of cells. In contrast, photodegradation allows external real-time spatial and temporal control over hydrogel degradation, and allows for staged and sequential release of cells. We synthesized and characterized a series of macromers incorporating photodegradbale ortho-nitrobenzyl (o-NB) groups in the macromer backbone. We formed hydrogels from these macromers via redox polymerization and quantified the apparent rate constants of degradation (k(app)) of each via photorheology at 370 nm, 10 mW/cm(2). Decreasing the number of aryl ethers on the o-NB group increases k(app), and changing the functionality from primary to seconday at the benzylic site dramatically increases k(app). Human mesenchymal stem cells (hMSCs) survive encapsulation in the hydrogels (90% viability postencapsulation). By exploiting the differences in reactivity of two different o-NB linkers, we quantitatively demonstrate the biased release of one stem cell population (green-fluoroescent protein expressing hMSCs) over another (red-fluorescent protein expressing hMSCs).

  DOI：

  10.1021/ja305280w