dipentafluorobenzyl azeleate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dipentafluorobenzyl azeleate
• 英文别名: Bis[(2,3,4,5,6-pentafluorophenyl)methyl] nonanedioate；bis[(2,3,4,5,6-pentafluorophenyl)methyl] nonanedioate
• 化学式: C₂₃H₁₈F₁₀O₄
• 分子量: 548.378
• InChiKey: HUCRNFFUEAFDES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  壬二酸 、 α-溴-2,3,4,5,6-五氟甲基苯酸酯 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成 dipentafluorobenzyl azeleate
  参考文献：
  名称：

  γ-Hydroxyalkenals Are Oxidatively Cleaved through Michael Addition of Acylperoxy Radicals and Fragmentation of Intermediate β-Hydroxyperesters

  摘要：

  Oxidative cleavage of arachidonate (C-20) and linoleate (C-18) phospholipids generates truncated C-8 or C-12 gamma-hydroxyalkenal phospholipids as well as C-5 or C-9 carboxyalkanoate phospholipids, which are abundant in atherosclerotic plaques. The gamma-hydroxyalkenals promote foam cell formation by scavenger receptor CD36-mediated endocytosis. The carboxyalkanoates are potent regulators of endothelial cell functions that may promote atherogenesis. We now report an unexpected biosynthetic interconnection; the carboxyalkanoates can be generated through oxidative cleavage of the gamma-hydroxyalkenals with the loss of three carbons. This unprecedented transformation is shown to involve Michael addition of an acylperoxy radical and fragmentation of the resulting beta-hydroxyperester.

  DOI：

  10.1021/ja048060i