2-(2-oxo-1,3,2-dioxaphospholan-2-yloxy)ethyl 2'-bromoisobutyrate | 779355-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧磷杂环戊烷
• 英文名称: 2-(2-oxo-1,3,2-dioxaphospholan-2-yloxy)ethyl 2'-bromoisobutyrate
• 英文别名: 2-[(2-Oxido-1,3,2-dioxaphospholan-2-ium-2-yl)oxy]ethyl 2-bromo-2-methylpropanoate；2-[(2-oxido-1,3,2-dioxaphospholan-2-ium-2-yl)oxy]ethyl 2-bromo-2-methylpropanoate
• CAS: 779355-73-6
• 化学式: C₈H₁₄BrO₆P
• 分子量: 317.073
• InChiKey: UWKVQYKEZGDUQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  356.3±25.0 °C(Predicted)
• 密度：
  1.55±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氯-2-氧-1,3,2-二氧磷杂环戊烷 、 ATRP 羟基引发剂 在 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以67.1%的产率得到2-(2-oxo-1,3,2-dioxaphospholan-2-yloxy)ethyl 2'-bromoisobutyrate
  参考文献：
  名称：

  Design of Biodegradable Amphiphilic Polymers:  Well-Defined Amphiphilic Polyphosphates with Hydrophilic Graft Chains via ATRP

  摘要：

  Novel biodegradable amphiphilic polymers composed of hydrophobic polyphosphate grafted with well-defined hydrophilic poly [2-methacryloyloxyethyl phosphorylcholine (MPC)] were newly synthesized. 2-Isopropyl-2-oxo-1,3,2-dioxaphospholane and 2-(2-oxo-1,3,2-dioxaphosphoroyloxyethyl-2-bromoisobutylate) (OPBB) were copolymerized by ring-opening polymerization using triisobutylaluminum as an initiator. Polyphosphates (PIBr) whose molecular weights were 3.4 x 10(4) g/mol with 3.0 units of OPBB and 3.7 x 10(4) g/mol with 10.5 units of OPBB were obtained. MPC was grafted from the OPBB sites in PIBr via atom transfer radical polymerization (ATRP). The molecular weights of the graft copolymers [PIBr-g-poly(MPC) (PMPC)] and the amphiphilicity of the graft copolymers were well controllable with polymerization time. The solution properties of various amphiphilic PIBr-g-PMPCs were investigated by the methods of surface tension measurement, light scattering, and fluorescence probe. PIBr-g-PMPC showed high surface activity. The critical micelle concentration (cmc) of the surface tension of the PIBr-g-PMPCs increased with an increase in the molecular weight and density of the PMPC chain. Above the cmc of PIBr-g-PMPC with 3.0 units of PMPC per PIBr, the polymer associated and formed nanosize-hydrogels (nanogels) (R-g = 26.2 nm) observed by a light scattering method and a fluorescence probe method. Degradation of the PIBr-g-PMPC was also investigated under various pH conditions. In a basic condition, the rate of hydrolysis of the graft copolymer was quite large. The polyphosphate of PIBr-g-PMPC completely degraded after only 3 days. PIBr-g-PMPCs were novel biodegradable amphiphilic polymers.

  DOI：

  10.1021/ma049043g

文献信息

• Design of Biodegradable Amphiphilic Polymers:  Well-Defined Amphiphilic Polyphosphates with Hydrophilic Graft Chains via ATRP
  作者：Yasuhiko Iwasaki、Kazunari Akiyoshi

  DOI：10.1021/ma049043g

  日期：2004.10.1

  Novel biodegradable amphiphilic polymers composed of hydrophobic polyphosphate grafted with well-defined hydrophilic poly [2-methacryloyloxyethyl phosphorylcholine (MPC)] were newly synthesized. 2-Isopropyl-2-oxo-1,3,2-dioxaphospholane and 2-(2-oxo-1,3,2-dioxaphosphoroyloxyethyl-2-bromoisobutylate) (OPBB) were copolymerized by ring-opening polymerization using triisobutylaluminum as an initiator. Polyphosphates (PIBr) whose molecular weights were 3.4 x 10(4) g/mol with 3.0 units of OPBB and 3.7 x 10(4) g/mol with 10.5 units of OPBB were obtained. MPC was grafted from the OPBB sites in PIBr via atom transfer radical polymerization (ATRP). The molecular weights of the graft copolymers [PIBr-g-poly(MPC) (PMPC)] and the amphiphilicity of the graft copolymers were well controllable with polymerization time. The solution properties of various amphiphilic PIBr-g-PMPCs were investigated by the methods of surface tension measurement, light scattering, and fluorescence probe. PIBr-g-PMPC showed high surface activity. The critical micelle concentration (cmc) of the surface tension of the PIBr-g-PMPCs increased with an increase in the molecular weight and density of the PMPC chain. Above the cmc of PIBr-g-PMPC with 3.0 units of PMPC per PIBr, the polymer associated and formed nanosize-hydrogels (nanogels) (R-g = 26.2 nm) observed by a light scattering method and a fluorescence probe method. Degradation of the PIBr-g-PMPC was also investigated under various pH conditions. In a basic condition, the rate of hydrolysis of the graft copolymer was quite large. The polyphosphate of PIBr-g-PMPC completely degraded after only 3 days. PIBr-g-PMPCs were novel biodegradable amphiphilic polymers.