17-tert-butyldimethylsilyloxylinoleic acid methyl ester | 672263-63-7

• 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: 17-tert-butyldimethylsilyloxylinoleic acid methyl ester
• CAS: 672263-63-7
• 化学式: C₂₅H₄₈O₃Si
• 分子量: 424.74
• InChiKey: WHYKLIKRPIQTIZ-JDQZXNMFSA-N

物化性质

• 沸点：
  458.1±45.0 °C(Predicted)
• 密度：
  0.895±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.97
• 重原子数：
  29.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  17-tert-butyldimethylsilyloxylinoleic acid methyl ester 在 吡啶 、 hog liver esterase 、 四丁基氟化铵 、 碘 、 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 phosphate buffer 、 二氯甲烷 为溶剂， 反应 37.08h， 生成 N-(17-dimethylphosphonooxylinoleoyl)glutamine
  参考文献：
  名称：

  N-(17-Phosphonooxylinolenoyl)glutamine and N-(17-phosphonooxylinoleoyl)glutamine from Insect Gut:  The First Backbone-Phosphorylated Fatty Acid Derivatives in Nature

  摘要：

  N-(17-Phosphonooxylinolenoyl)glutamine (1) and N-(17-phosphonooxylinoleoyl)glutamine (2) were isolated from the regurgitate of Spodoptora exigua and identified as the first natural alkyl chain-phosphorylated fatty acid derivatives. The compounds were characterized by HPLC-MS/MS and the assigned structures confirmed by synthesis via a dissymmetric bis-Wittig approach as the key reaction. Rearing of the larvae on a diet enriched with inorganic phosphate increased the amount of the phosphorylated N-acyl glutamines in the regurgitate.

  DOI：

  10.1021/jo035382g
• 作为产物：
  描述：

  9-氧代壬酸甲酯 、 1,3-bis(triphenylphosphino)propane dibromide 、 5-(tert-butyldimethylsilanyloxy)hexanal 在 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以20%的产率得到17-tert-butyldimethylsilyloxylinoleic acid methyl ester
  参考文献：
  名称：

  N-(17-Phosphonooxylinolenoyl)glutamine and N-(17-phosphonooxylinoleoyl)glutamine from Insect Gut:  The First Backbone-Phosphorylated Fatty Acid Derivatives in Nature

  摘要：

  N-(17-Phosphonooxylinolenoyl)glutamine (1) and N-(17-phosphonooxylinoleoyl)glutamine (2) were isolated from the regurgitate of Spodoptora exigua and identified as the first natural alkyl chain-phosphorylated fatty acid derivatives. The compounds were characterized by HPLC-MS/MS and the assigned structures confirmed by synthesis via a dissymmetric bis-Wittig approach as the key reaction. Rearing of the larvae on a diet enriched with inorganic phosphate increased the amount of the phosphorylated N-acyl glutamines in the regurgitate.

  DOI：

  10.1021/jo035382g

文献信息

• <i>N</i>-(17-Phosphonooxylinolenoyl)glutamine and <i>N</i>-(17-phosphonooxylinoleoyl)glutamine from Insect Gut:  The First Backbone-Phosphorylated Fatty Acid Derivatives in Nature
  作者：Dieter Spiteller、Neil J. Oldham、Wilhelm Boland

  DOI：10.1021/jo035382g

  日期：2004.2.1

  N-(17-Phosphonooxylinolenoyl)glutamine (1) and N-(17-phosphonooxylinoleoyl)glutamine (2) were isolated from the regurgitate of Spodoptora exigua and identified as the first natural alkyl chain-phosphorylated fatty acid derivatives. The compounds were characterized by HPLC-MS/MS and the assigned structures confirmed by synthesis via a dissymmetric bis-Wittig approach as the key reaction. Rearing of the larvae on a diet enriched with inorganic phosphate increased the amount of the phosphorylated N-acyl glutamines in the regurgitate.