(S)-2-Fluoro-tetradec-11-ynoic acid | 174293-53-9

• 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: (S)-2-Fluoro-tetradec-11-ynoic acid
• 英文别名: (2S)-2-fluorotetradec-11-ynoic acid
• CAS: 174293-53-9
• 化学式: C₁₄H₂₃FO₂
• 分子量: 242.334
• InChiKey: VOYDXDPCGKRZSZ-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-Fluoro-tetradec-11-ynoic acid 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 Acetic acid (S)-2-fluoro-tetradec-11-ynyl ester
  参考文献：
  名称：

  Enantioselective synthesis of 2-fluoro carboxylic acids from Trichloromethyl carbinols: an efficient approach to chiral fluorine introduction into insect sex pheromones

  摘要：

  Chiral syntheses of 2-fluoro carboxylic acids were achieved (ee greater than or equal to 92 %, yield 50-60 %) by stereoselective conversion (with inversion of configuration) of optically active trichloromethyl carbinols to fluoroacids with tetrabutylammonium fluoride. Fluorinated pheromone analogs of the European corn borer, Ostrinia nubilalis, and of the beet armyworm, Spodoptera exigua, were synthesized.

  DOI：

  10.1016/0957-4166(95)00415-7
• 作为产物：
  描述：

  (R)-1,1,1-Trichloro-tetradec-11-yn-2-ol 在 四丁基氟化铵 、 三乙胺 、 cesium fluoride 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以53%的产率得到(S)-2-Fluoro-tetradec-11-ynoic acid
  参考文献：
  名称：

  Enantioselective synthesis of 2-fluoro carboxylic acids from Trichloromethyl carbinols: an efficient approach to chiral fluorine introduction into insect sex pheromones

  摘要：

  Chiral syntheses of 2-fluoro carboxylic acids were achieved (ee greater than or equal to 92 %, yield 50-60 %) by stereoselective conversion (with inversion of configuration) of optically active trichloromethyl carbinols to fluoroacids with tetrabutylammonium fluoride. Fluorinated pheromone analogs of the European corn borer, Ostrinia nubilalis, and of the beet armyworm, Spodoptera exigua, were synthesized.

  DOI：

  10.1016/0957-4166(95)00415-7