2-(2-bromopropanoyloxy)-4-pentynoic acid | 1309656-53-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-(2-bromopropanoyloxy)-4-pentynoic acid
• CAS: 1309656-53-8
• 化学式: C₈H₉BrO₄
• 分子量: 249.061
• InChiKey: GSHOVFUYEQTOHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.79
• 重原子数：
  13.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(2-bromopropanoyloxy)-4-pentynoic acid 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 以43%的产率得到1,4-Dioxane-2,5-dione, 3-methyl-6-(2-propyn-1-yl)-
  参考文献：
  名称：

  Functional Polylactide-g-Paclitaxel–Poly(ethylene glycol) by Azide–Alkyne Click Chemistry

  摘要：

  Functional polylactide-g-paclitaxel poly(ethylene glycol), a novel graft polymer drug conjugate (GPDC) with paclitaxel (PTXL) as the divalent agent to bridge between the degradable polylactide (PLA)-based backbone and hydrophilic poly(ethylene glycol) (PEG) side chains, were prepared by the copper-catalyzed azide-alkyne cycloaddition reaction of acetylene-functionalized polylactide (PLA) with azide-functionalized PTXL PEG conjugate. The acetylene-functionalized PLA was prepared by ring-opening copolymerization (ROCP) of acetylene-functionalized LA monomer with L-lactide (LA). The azide-functionalized PTXL PEG conjugate was prepared by multistep organic synthesis. The well-controlled chemical structures of the GPDC and its precursors were verified by H-1 NMR and GPC characterizations. DLS analysis indicated that GPDC molecules assembled in water to form nanoparticles with sizes of 8-40 nm. GPC analysis of buffer solutions (pH = 5.5 and 7.4) of the GPDC suggested the occurrence of multiple hydrolysis reactions under the experimental conditions, which resulted in the release of PTXL moieties and the cleavage of PLA-based backbone.

  DOI：

  10.1021/ma2005102
• 作为产物：
  描述：

  2-羟基-4-戊炔酸 、 2-溴丙酰溴 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 以95%的产率得到2-(2-bromopropanoyloxy)-4-pentynoic acid
  参考文献：
  名称：

  Functional Polylactide-g-Paclitaxel–Poly(ethylene glycol) by Azide–Alkyne Click Chemistry

  摘要：

  Functional polylactide-g-paclitaxel poly(ethylene glycol), a novel graft polymer drug conjugate (GPDC) with paclitaxel (PTXL) as the divalent agent to bridge between the degradable polylactide (PLA)-based backbone and hydrophilic poly(ethylene glycol) (PEG) side chains, were prepared by the copper-catalyzed azide-alkyne cycloaddition reaction of acetylene-functionalized polylactide (PLA) with azide-functionalized PTXL PEG conjugate. The acetylene-functionalized PLA was prepared by ring-opening copolymerization (ROCP) of acetylene-functionalized LA monomer with L-lactide (LA). The azide-functionalized PTXL PEG conjugate was prepared by multistep organic synthesis. The well-controlled chemical structures of the GPDC and its precursors were verified by H-1 NMR and GPC characterizations. DLS analysis indicated that GPDC molecules assembled in water to form nanoparticles with sizes of 8-40 nm. GPC analysis of buffer solutions (pH = 5.5 and 7.4) of the GPDC suggested the occurrence of multiple hydrolysis reactions under the experimental conditions, which resulted in the release of PTXL moieties and the cleavage of PLA-based backbone.

  DOI：

  10.1021/ma2005102