γ-Fluoro-γ-butyrolactone | 2343-90-0

• 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: γ-Fluoro-γ-butyrolactone
• 英文别名: 5-fluoro-5-pentanolide；2(3H)-Furanone, 5-fluorodihydro-；5-fluorooxolan-2-one
• CAS: 2343-90-0
• 化学式: C₄H₅FO₂
• 分子量: 104.081
• InChiKey: UKLWMJXVBPVEPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  γ-丁内酯 在 Et₃NHF*5HF 作用下， 以61%的产率得到γ-Fluoro-γ-butyrolactone
  参考文献：
  名称：

  Electroorganic synthesis under solvent-free conditions. Highly regioselective anodic monofluorination of cyclic ethers, lactones, and a cyclic carbonate

  摘要：

  Regioselective anodic fluorination of cyclic ethers, lactones, and a cyclic carbonate in Et4NF.nHF (n = 4, 5) and Et3N.5HF without a solvent was successfully carried out to give the corresponding monofluorinated products in moderate yields. This is the first report of direct electochemical fluorination of cyclic ethers, lactones, and a cyclic carbonate using anodic fluorination. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00047-3

文献信息

• Direct fluorination of γ-butyrolactone
  作者：Yukio Sasaki、Ryo Ebara、Noritoshi Nanbu、Masahiro Takehara、Makoto Ue

  DOI：10.1016/s0022-1139(01)00343-8

  日期：2001.3

  gamma -Butyrolactone was fluorinated by molecular fluorine to obtain its mono-fluorinated derivatives for possible lithium battery electrolyte application. The reaction was carried out at 30 degreesC by introducing 20% F-2/N-2 gas into gamma -butyrolactone without solvent. Major products were beta -fluoro-gamma -butyrolactone and gamma -fluoro-gamma -butyrolactone, which cannot be obtained by conventional organic synthesis. Selectivity to gamma -isomer was enhanced by the addition of NaF as a HF scavenger. (C) 2001 Elsevier Science B.V. All rights reserved.
• Electroorganic synthesis under solvent-free conditions. Highly regioselective anodic monofluorination of cyclic ethers, lactones, and a cyclic carbonate
  作者：Masaru Hasegawa、Hideki Ishii、Toshio Fuchigami

  DOI：10.1016/s0040-4039(02)00047-3

  日期：2002.2

  Regioselective anodic fluorination of cyclic ethers, lactones, and a cyclic carbonate in Et4NF.nHF (n = 4, 5) and Et3N.5HF without a solvent was successfully carried out to give the corresponding monofluorinated products in moderate yields. This is the first report of direct electochemical fluorination of cyclic ethers, lactones, and a cyclic carbonate using anodic fluorination. (C) 2002 Elsevier Science Ltd. All rights reserved.