3-fluoro-4,4-dimethyl-dihydrofuran-2(3H)-one | 220294-23-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3-fluoro-4,4-dimethyl-dihydrofuran-2(3H)-one
• 英文别名: 3-Fluoro-4,4-dimethyloxolan-2-one
• CAS: 220294-23-5
• 化学式: C₆H₉FO₂
• 分子量: 132.135
• InChiKey: XRTLCHKDNFCZQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4,4-Dimethyl-2-oxooxolan-3-yl) trifluoromethanesulfonate 在 tetrabutylammonium fluoride hydrofluoride 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 生成 3-fluoro-4,4-dimethyl-dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Nucleophilic Fluorination of Triflates by Tetrabutylammonium Bifluoride

  摘要：

  Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.

  DOI：

  10.1021/jo8015659