1,2-didecanoyl-3-acryloylglycerol | 557105-24-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-didecanoyl-3-acryloylglycerol
• 英文别名: 1,2-Didecanoyl-3-acrylylglycerol；(2-decanoyloxy-3-prop-2-enoyloxypropyl) decanoate
• CAS: 557105-24-5
• 化学式: C₂₆H₄₆O₆
• 分子量: 454.648
• InChiKey: SFWBNBXPOPAQAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  32
• 可旋转键数：
  25
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  溴苯 、 1,2-didecanoyl-3-acryloylglycerol 在 三正丁胺 、 三(邻甲基苯基)磷 、 palladium dichloride 作用下， 反应 0.33h， 生成 1,2-didecanoyl-3-trans-cinnamoylglycerol
  参考文献：
  名称：

  甘油的丙烯酸化：功能化脂质的前体

  摘要：

  AbstractWith the objective of expanding the number of functionalized lipids available, the reactive vinyl group of acrylic acid was introduced to triacylglycerol by esterification of glycerol. Didecanoylacryloylglycerol was synthesized from decanoic and acrylic acids and glycerol using K2O as catalyst. 2 g (21.7 mmol) glycerol, 11.3 g (65.4 mmol) decanoic acid, 6.2 g (86.1 mmol) acrylic acid, 60 ml hexane, and 400 mg K2O were added to 300‐ml closed stainless steel reactor and maintained at 200 °C for 5 h. The resulting product, designated DDA, was isolated at about 40% yield based on the acylglycerol products. The other products included tridecanoylglycerol, diacryloyldecanoylglycerol, and the diacylglycerols of these acids. DDA was then converted to functionalized lipids by the Michael addition and Heck reaction. The Michael addition of thiophenol and 4‐bromothiophenol yielded the corresponding linear thioethers whereas and Heck reaction products from bromobenzene and bromoanisole yielded triacylglycerols containing trans‐cinnamic acid and trans‐(4‐methoxy)cinnamic acid, respectively.

  DOI：

  10.1007/s11746-011-1950-5
• 作为产物：
  描述：

  正癸酸 、 甘油 、 丙烯酸 在 potassium oxide 作用下， 以 正己烷 为溶剂， 200.0 ℃ 、4.0 MPa 条件下， 反应 5.0h， 生成 1,3-didecanoyl-2-acryloylglycerol 、 1,2-didecanoyl-3-acryloylglycerol
  参考文献：
  名称：

  甘油的丙烯酸化：功能化脂质的前体

  摘要：

  AbstractWith the objective of expanding the number of functionalized lipids available, the reactive vinyl group of acrylic acid was introduced to triacylglycerol by esterification of glycerol. Didecanoylacryloylglycerol was synthesized from decanoic and acrylic acids and glycerol using K2O as catalyst. 2 g (21.7 mmol) glycerol, 11.3 g (65.4 mmol) decanoic acid, 6.2 g (86.1 mmol) acrylic acid, 60 ml hexane, and 400 mg K2O were added to 300‐ml closed stainless steel reactor and maintained at 200 °C for 5 h. The resulting product, designated DDA, was isolated at about 40% yield based on the acylglycerol products. The other products included tridecanoylglycerol, diacryloyldecanoylglycerol, and the diacylglycerols of these acids. DDA was then converted to functionalized lipids by the Michael addition and Heck reaction. The Michael addition of thiophenol and 4‐bromothiophenol yielded the corresponding linear thioethers whereas and Heck reaction products from bromobenzene and bromoanisole yielded triacylglycerols containing trans‐cinnamic acid and trans‐(4‐methoxy)cinnamic acid, respectively.

  DOI：

  10.1007/s11746-011-1950-5