12-(2-oxo-1,3,2-dioxaphospholane-2-yloxy)dodecylmethacrylate | 141547-25-3

• 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: 12-(2-oxo-1,3,2-dioxaphospholane-2-yloxy)dodecylmethacrylate
• CAS: 141547-25-3
• 化学式: C₁₈H₃₃O₆P
• 分子量: 376.43
• InChiKey: CPRQPEVHQZIOSD-UHFFFAOYSA-N

物化性质

• 沸点：
  448.4±14.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  25.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  12-(2-oxo-1,3,2-dioxaphospholane-2-yloxy)dodecylmethacrylate 、 三甲胺 以 乙腈 为溶剂， 以51%的产率得到12-(methacryloyloxy)dodecylphosphocholine
  参考文献：
  名称：

  Synthesis, characterization and properties of a new polymerisable surfactant: 12-Methacryloyl dodecylphosphocholine

  摘要：

  A new polymerizable surfactant, 12-methacryloyl dodecylphosphocholine (MDPC), has been synthesized using a three-step procedure in moderate yield. Phase transitions were characterized by DSC and phase behavior in water was determined by surface tension and polarizing microscopy. MDPC showed typical surfactant behavior and self-aggregated to micelles above a distinct concentration. The critical micelle concentration (CMC) of MDPC was determined to be 5 x 10(-4) mol/L MDPC showed mesomorphic properties between 75 and 86 degrees C as studied by differential scanning calorimetry (DSC). The formation of black lipid membranes was further investigated. The methacrylate functionalized MDPC could form a bilayer membrane (BLM) although it was very unstable (collapsed after 10-30s). However, it was possible to form stable BLMs in mixture with non-polymerizable two chain phospholipids, i.e. asolectin and diphytanoyl phosphatidylcholine (DPhPC). Stable bilayers could be obtained up to a MDPC content of 50 mol%. Gramicidin A was incorporated into MDPC/DPhPC membranes and exhibited ion-channel activity shown by single channel conductivity measurements. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2010.03.001
• 作为产物：
  描述：

  12-羟基十二碳基甲基丙烯酸酯 、 2-氯-2-氧-1,3,2-二氧磷杂环戊烷 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以89%的产率得到12-(2-oxo-1,3,2-dioxaphospholane-2-yloxy)dodecylmethacrylate
  参考文献：
  名称：

  Synthesis, characterization and properties of a new polymerisable surfactant: 12-Methacryloyl dodecylphosphocholine

  摘要：

  A new polymerizable surfactant, 12-methacryloyl dodecylphosphocholine (MDPC), has been synthesized using a three-step procedure in moderate yield. Phase transitions were characterized by DSC and phase behavior in water was determined by surface tension and polarizing microscopy. MDPC showed typical surfactant behavior and self-aggregated to micelles above a distinct concentration. The critical micelle concentration (CMC) of MDPC was determined to be 5 x 10(-4) mol/L MDPC showed mesomorphic properties between 75 and 86 degrees C as studied by differential scanning calorimetry (DSC). The formation of black lipid membranes was further investigated. The methacrylate functionalized MDPC could form a bilayer membrane (BLM) although it was very unstable (collapsed after 10-30s). However, it was possible to form stable BLMs in mixture with non-polymerizable two chain phospholipids, i.e. asolectin and diphytanoyl phosphatidylcholine (DPhPC). Stable bilayers could be obtained up to a MDPC content of 50 mol%. Gramicidin A was incorporated into MDPC/DPhPC membranes and exhibited ion-channel activity shown by single channel conductivity measurements. (C) 2010 Elsevier Ireland Ltd. All rights reserved.

  DOI：

  10.1016/j.chemphyslip.2010.03.001