(S)-2-Hydroxy-propionic acid (S)-1-[1-methyl-2-(2-methyl-acryloylamino)-ethoxycarbonyl]-ethyl ester | 675589-71-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: (S)-2-Hydroxy-propionic acid (S)-1-[1-methyl-2-(2-methyl-acryloylamino)-ethoxycarbonyl]-ethyl ester
• 英文别名: [(2S)-1-[1-(2-methylprop-2-enoylamino)propan-2-yloxy]-1-oxopropan-2-yl] (2S)-2-hydroxypropanoate
• CAS: 675589-71-6
• 化学式: C₁₃H₂₁NO₆
• 分子量: 287.313
• InChiKey: RYHNJKLOXPXTMO-AGROOBSYSA-N

物化性质

• 沸点：
  465.3±43.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-2-Hydroxy-propionic acid (S)-1-[1-methyl-2-(2-methyl-acryloylamino)-ethoxycarbonyl]-ethyl ester 在 phosphate buffer saline 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(2-羟基丙基)甲基丙烯酰胺
  参考文献：
  名称：

  Degradation Mechanism and Kinetics of Thermosensitive Polyacrylamides Containing Lactic Acid Side Chains

  摘要：

  Diblock copolymers of poly(N-isopropylacrylamide-co-N-(2-hydroxypropyl)methacrylamide lactate) (poly(NIPAAm-co-HPMAm-lactate)) as a thermosensitive block and poly(ethylene glycol) (PEG) as a hydrophilic block form polymeric micelles above the cloud point (CP) of the temperature-sensitive block. Destabilization of these micelles occurs upon hydrolysis of the lactate side chains. Here we report on the degradation kinetics of the HPMAm-mono(di)lactate monomers and their copolymers with NIPAAm. The degradation of the monomers and polymers in their soluble state (thus below their CP) followed normal ester hydrolysis behavior: the degradation rate increased with temperature, pH (from pH 7.5 to 11), and dielectric constant of the medium. Above the CP, where the polymers are in a precipitated state, a significant retardation of the polymer degradation occurred due to a decrease of dielectric constant of the local environment of the precipitated polymer. This study shows that it is possible to predict the rate of formation of HPMAm in NIPAAm-co-HPAIAm-lactate copolymers which results in an increase of the overall hydrophilicity of the polymers and destabilization of polymeric micelles based on poly(NIPAAm-co-HPMAm-lactate).

  DOI：

  10.1021/ma034381n
• 作为产物：
  描述：

  N-(2-羟基丙基)甲基丙烯酰胺 、 L-丙交酯 在 stannous octoate 、 4-甲氧基苯酚 作用下， 反应 5.0h， 生成 (S)-2-Hydroxy-propionic acid 1-methyl-2-(2-methyl-acryloylamino)-ethyl ester 、 (S)-2-Hydroxy-propionic acid (S)-1-[1-methyl-2-(2-methyl-acryloylamino)-ethoxycarbonyl]-ethyl ester
  参考文献：
  名称：

  Degradation Mechanism and Kinetics of Thermosensitive Polyacrylamides Containing Lactic Acid Side Chains

  摘要：

  Diblock copolymers of poly(N-isopropylacrylamide-co-N-(2-hydroxypropyl)methacrylamide lactate) (poly(NIPAAm-co-HPMAm-lactate)) as a thermosensitive block and poly(ethylene glycol) (PEG) as a hydrophilic block form polymeric micelles above the cloud point (CP) of the temperature-sensitive block. Destabilization of these micelles occurs upon hydrolysis of the lactate side chains. Here we report on the degradation kinetics of the HPMAm-mono(di)lactate monomers and their copolymers with NIPAAm. The degradation of the monomers and polymers in their soluble state (thus below their CP) followed normal ester hydrolysis behavior: the degradation rate increased with temperature, pH (from pH 7.5 to 11), and dielectric constant of the medium. Above the CP, where the polymers are in a precipitated state, a significant retardation of the polymer degradation occurred due to a decrease of dielectric constant of the local environment of the precipitated polymer. This study shows that it is possible to predict the rate of formation of HPMAm in NIPAAm-co-HPAIAm-lactate copolymers which results in an increase of the overall hydrophilicity of the polymers and destabilization of polymeric micelles based on poly(NIPAAm-co-HPMAm-lactate).

  DOI：

  10.1021/ma034381n