16-octadecenoic acid methyl ester | 17257-44-2

• 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: 16-octadecenoic acid methyl ester
• 英文别名: methyl 16-octadecenoic acid ester；methyl ester 16-octadecenoic acid；methyl octadec-16-enoate；Methyl-octadec-16-enoat
• CAS: 17257-44-2；42199-41-7；56554-49-5
• 化学式: C₁₉H₃₆O₂
• 分子量: 296.494
• InChiKey: NJOFCKBMWIDUGP-UHFFFAOYSA-N

物化性质

• 沸点：
  364.3±11.0 °C(Predicted)
• 密度：
  0.873±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  21
• 可旋转键数：
  16
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  16-octadecenoic acid methyl ester 在 吡啶 、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 29.0h， 生成
  参考文献：
  名称：

  欧米茄功能化脂肪酸，醇和醚通过烯烃复分解反应

  摘要：

  AbstractMethyl 17‐hydroxy stearate was converted to methyl octadec‐16‐enoate using copper sulfate adsorbed on silica gel. This compound served as a useful substrate for the olefin metathesis reaction. As a result, several fatty acids with novel functional groups at the ω‐end were prepared: a glyceryl ether attached at the 18‐carbon, an aromatic fatty acid from eugenol, and a ferrocenyl fatty acid. By employing the unsaturated fatty alcohol, other groups were introduced, namely the terminal fluoride, bromide, and iodide were prepared, as was a thiol derivative. The penultimate and omega olefins reported here should serve as building blocks that allow fatty acids to make a greater contribution to a range of emerging technological areas.

  DOI：

  10.1007/s11746-012-2015-0
• 作为产物：
  描述：

  甲基17-羟基硬脂酸酯 在 copper sulfate/silica reagent 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以66%的产率得到16-octadecenoic acid methyl ester
  参考文献：
  名称：

  欧米茄功能化脂肪酸，醇和醚通过烯烃复分解反应

  摘要：

  AbstractMethyl 17‐hydroxy stearate was converted to methyl octadec‐16‐enoate using copper sulfate adsorbed on silica gel. This compound served as a useful substrate for the olefin metathesis reaction. As a result, several fatty acids with novel functional groups at the ω‐end were prepared: a glyceryl ether attached at the 18‐carbon, an aromatic fatty acid from eugenol, and a ferrocenyl fatty acid. By employing the unsaturated fatty alcohol, other groups were introduced, namely the terminal fluoride, bromide, and iodide were prepared, as was a thiol derivative. The penultimate and omega olefins reported here should serve as building blocks that allow fatty acids to make a greater contribution to a range of emerging technological areas.

  DOI：

  10.1007/s11746-012-2015-0

文献信息

• Omega-Functionalized Fatty Acids, Alcohols, and Ethers via Olefin Metathesis
  作者：Jonathan A. Zerkowski、Daniel K. Y. Solaiman

  DOI：10.1007/s11746-012-2015-0

  日期：——

  AbstractMethyl 17‐hydroxy stearate was converted to methyl octadec‐16‐enoate using copper sulfate adsorbed on silica gel. This compound served as a useful substrate for the olefin metathesis reaction. As a result, several fatty acids with novel functional groups at the ω‐end were prepared: a glyceryl ether attached at the 18‐carbon, an aromatic fatty acid from eugenol, and a ferrocenyl fatty acid. By employing the unsaturated fatty alcohol, other groups were introduced, namely the terminal fluoride, bromide, and iodide were prepared, as was a thiol derivative. The penultimate and omega olefins reported here should serve as building blocks that allow fatty acids to make a greater contribution to a range of emerging technological areas.