1,1'-(4,4'-(4,4'-(ethane-1,2-diylbis(azanediyl))bis(4-oxobutane-4,1-diyl))bis(oxy)bis(5-methoxy-2-nitro-4,1-phenylene))bis(ethane-1,1-diyl)bis(2-methyl acrylate) | 1352127-37-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,1'-(4,4'-(4,4'-(ethane-1,2-diylbis(azanediyl))bis(4-oxobutane-4,1-diyl))bis(oxy)bis(5-methoxy-2-nitro-4,1-phenylene))bis(ethane-1,1-diyl)bis(2-methyl acrylate)
• CAS: 1352127-37-7
• 化学式: C₃₆H₄₆N₄O₁₄
• 分子量: 758.78
• InChiKey: LMEXVLWTERCEET-UHFFFAOYSA-N

物化性质

• 沸点：
  927.8±65.0 °C(Predicted)
• 密度：
  1.244±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.13
• 重原子数：
  54.0
• 可旋转键数：
  23.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  234.0
• 氢给体数：
  2.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  1,1'-(4,4'-(4,4'-(ethane-1,2-diylbis(azanediyl))bis(4-oxobutane-4,1-diyl))bis(oxy)bis(5-methoxy-2-nitro-4,1-phenylene))bis(ethane-1,1-diyl)bis(2-methyl acrylate) 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Dual Stimuli-Responsive Poly(2-hydroxyethyl methacrylate-co-methacrylic acid) Microgels Based on Photo-Cleavable Cross-Linkers: pH-Dependent Swelling and Light-Induced Degradation

  摘要：

  Dual stimuli-responsive p(HEMA-co-MAA) microgels were prepared in a facile way by inverse miniemulsion copolymerization of 2-hydroxyethyl methacrylate (HEMA) with methacrylic acid (MAA) and two kinds of newly synthesized photodegradable cross-linkers. The pH-dependent swelling behavior induced by the protonation/deprotonation of the methacrylic acid groups in the network-forming polymer was investigated by means of the particle volume change as determined by DLS measurements. Photolytic degradation experiments were conducted by irradiation with UV light which led to particle disintegration caused by cleavage of the photolabile cross-linking points. The degradation behavior of the microgels was investigated with respect to degradation rates and changes in the degree of swelling. Those parameters were found to depend on the pH value of the solvent, the light intensities, and the irradiation wavelengths applied. For similar conditions, the degradation profile was demonstrated to strongly depend not only on the molecular structure of the cross-linking molecule but also on the molecular weight of the network-forming copolymers. The particular combination of the stimuli described is designed as a new strategy to two different swelling/degradation profiles. This dual stimuli-responsiveness was shown to enable the efficient loading and subsequent release of myoglobin as a model protein. Here a slow diffusion controlled release (induced by changes of the pH) was combined with a fast degradation controlled (induced by irradiation) on-demand release. This novel two-step release profile is proposed to bear great potential for delivery applications.

  DOI：

  10.1021/ma201706r
• 作为产物：
  描述：

  4-(4-乙酰基-2-甲氧基-5-硝基苯氧基)丁酸甲酯 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 53.0h， 生成 1,1'-(4,4'-(4,4'-(ethane-1,2-diylbis(azanediyl))bis(4-oxobutane-4,1-diyl))bis(oxy)bis(5-methoxy-2-nitro-4,1-phenylene))bis(ethane-1,1-diyl)bis(2-methyl acrylate)
  参考文献：
  名称：

  Dual Stimuli-Responsive Poly(2-hydroxyethyl methacrylate-co-methacrylic acid) Microgels Based on Photo-Cleavable Cross-Linkers: pH-Dependent Swelling and Light-Induced Degradation

  摘要：

  Dual stimuli-responsive p(HEMA-co-MAA) microgels were prepared in a facile way by inverse miniemulsion copolymerization of 2-hydroxyethyl methacrylate (HEMA) with methacrylic acid (MAA) and two kinds of newly synthesized photodegradable cross-linkers. The pH-dependent swelling behavior induced by the protonation/deprotonation of the methacrylic acid groups in the network-forming polymer was investigated by means of the particle volume change as determined by DLS measurements. Photolytic degradation experiments were conducted by irradiation with UV light which led to particle disintegration caused by cleavage of the photolabile cross-linking points. The degradation behavior of the microgels was investigated with respect to degradation rates and changes in the degree of swelling. Those parameters were found to depend on the pH value of the solvent, the light intensities, and the irradiation wavelengths applied. For similar conditions, the degradation profile was demonstrated to strongly depend not only on the molecular structure of the cross-linking molecule but also on the molecular weight of the network-forming copolymers. The particular combination of the stimuli described is designed as a new strategy to two different swelling/degradation profiles. This dual stimuli-responsiveness was shown to enable the efficient loading and subsequent release of myoglobin as a model protein. Here a slow diffusion controlled release (induced by changes of the pH) was combined with a fast degradation controlled (induced by irradiation) on-demand release. This novel two-step release profile is proposed to bear great potential for delivery applications.

  DOI：

  10.1021/ma201706r