1,1,1,3-tetrafluoroheptadecane-2,2-diol | 1071001-58-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1,1,3-tetrafluoroheptadecane-2,2-diol
• CAS: 1071001-58-5
• 化学式: C₁₇H₃₂F₄O₂
• 分子量: 344.433
• InChiKey: RKMJZGJIZZDAQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  23
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,1,1,3-tetrafluoroheptadecane-2,2-diol 在 (三氟甲基)三甲基硅烷 、 cesium fluoride 、 盐酸 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 36.5h， 以58%的产率得到1,1,1,3-tetrafluoro-heptadecan-2-one
  参考文献：
  名称：

  Synthesis of Polyfluoro Ketones for Selective Inhibition of Human Phospholipase A₂ Enzymes

  摘要：

  The development of selective inhibitors for individual PLA(2) enzymes is necessary in order to target PLA(2)-specific signaling pathways, but it is challenging due to the observed promiscuity of known PLA(2) inhibitors. In the current work, we present the development and application of a variety of synthetic routes to produce pentafluoro, tetrafluoro, and trifluoro derivatives of activated carbonyl groups in order to screen for selective inhibitors and characterize the chemical properties that can lead to selective inhibition. Our results demonstrate that the pentafluoroethyl ketone functionality favors selective inhibition of the GVIA iPLA(2), a very important enzyme for which specific, potent, reversible inhibitors are needed. We find that 1,1,1,2,2-pentafluoro-7-phenyl-heptan-3-one (FKGK11) is a selective inhibitor of GVIA iPLA(2) (X-1(50) = 0.0073). Furthermore, we conclude that the introduction of an additional fluorine atom at the alpha' position of a trifluoromethyl ketone constitutes an important strategy for the development of new potent GVIA iPLA(2) inhibitors.

  DOI：

  10.1021/jm800649q