methyl 17-(prop-2-yn-1-yloxy)octadecanoate | 1204823-07-3

• 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: methyl 17-(prop-2-yn-1-yloxy)octadecanoate
• CAS: 1204823-07-3
• 化学式: C₂₂H₄₀O₃
• 分子量: 352.558
• InChiKey: KMKDCRUEPWEQRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  25.0
• 可旋转键数：
  18.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 17-(prop-2-yn-1-yloxy)octadecanoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  可点击的脂质：叠氮基和炔基脂肪酸以及三酰基甘油

  摘要：

  AbstractHydroxy fatty acids (FAs), which were isolated from glycolipids that can be prepared fermentatively from fats and oils, have been synthetically modified to contain azide and alkyne functional groups. These particular functional groups were chosen because they can participate in a copper‐catalyzed reaction that combines them to form a 1,4‐triazole, known as a “click” reaction, which has been widely used in a variety of fields but remains underutilized in FA chemistry. Depending on the starting hydroxy FA, these groups can be close to the carboxy unit (using 3‐hydroxydecanoate) and hence the polar glycerol group, or distant from it (using 17‐hydroxyoctadecanoate). These structural alternatives will impart different properties to the triacylglycerols that are subsequently prepared from the modified FA. Finally, the click reaction was used to conjugate triacylglycerols to each other and to other molecules such as a glycolipid or a protected amine.

  DOI：

  10.1007/s11746-009-1442-z
• 作为产物：
  描述：

  甲基17-羟基硬脂酸酯 、 prop-2-yn-1-yl 2,2,2-trichloroacetimidate 在 三氟甲磺酸 作用下， 以 二氯甲烷 、 环己烷 为溶剂， 以830 mg的产率得到methyl 17-(prop-2-yn-1-yloxy)octadecanoate
  参考文献：
  名称：

  可点击的脂质：叠氮基和炔基脂肪酸以及三酰基甘油

  摘要：

  AbstractHydroxy fatty acids (FAs), which were isolated from glycolipids that can be prepared fermentatively from fats and oils, have been synthetically modified to contain azide and alkyne functional groups. These particular functional groups were chosen because they can participate in a copper‐catalyzed reaction that combines them to form a 1,4‐triazole, known as a “click” reaction, which has been widely used in a variety of fields but remains underutilized in FA chemistry. Depending on the starting hydroxy FA, these groups can be close to the carboxy unit (using 3‐hydroxydecanoate) and hence the polar glycerol group, or distant from it (using 17‐hydroxyoctadecanoate). These structural alternatives will impart different properties to the triacylglycerols that are subsequently prepared from the modified FA. Finally, the click reaction was used to conjugate triacylglycerols to each other and to other molecules such as a glycolipid or a protected amine.

  DOI：

  10.1007/s11746-009-1442-z