cis-4-fluoro-5-phenyldihydrofuran-2(3H)-one

• 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: cis-4-fluoro-5-phenyldihydrofuran-2(3H)-one
• 英文别名: (4RS,5RS)-4-fluoro-5-phenyldihydrofuran-2(3H)-one；(4S,5S)-4-fluoro-5-phenyloxolan-2-one
• 化学式: C₁₀H₉FO₂
• 分子量: 180.179
• InChiKey: BGPVQZDYOHGGBO-WPRPVWTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  反-苯乙烯乙酸 在 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 48.0h， 生成 trans-4-fluoro-5-phenyldihydrofuran-2(3H)-one 、 cis-4-fluoro-5-phenyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  Fluorolactonization of unsaturated carboxylic acids with F-TEDA-BF4 in ionic liquids

  摘要：

  Fluorolactonization of unsaturated carboxylic acids under action of the electrophilic reagent F-TEDA-BF4 in ionic liquids (ILs) has been studied. This reaction proceeds in ILs faster and provides a better stereoselectivity in comparison to acetonitrile as reaction media. Gem-difluorinated gamma-lactones have been synthesized by interaction of unsaturated carboxylic acids with F-TEDA-BF4 in ILs. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.124

文献信息

• Silver-Mediated Decarboxylative Fluorination of Paraconic Acids: A Direct Entry to β-Fluorinated γ-Butyrolactones
  作者：Supasorn Phae-nok、Darunee Soorukram、Chutima Kuhakarn、Vichai Reutrakul、Manat Pohmakotr

  DOI：10.1002/ejoc.201500023

  日期：2015.5

  silver(I)-mediated decarboxylative fluorination of paraconic acids using Selectfluor® as a fluorine source is reported. Readily available paraconic acids undergo decarboxylative fluorination with Selectfluor® mediated by AgNO3 to give the corresponding β-fluorinated γ-butyrolactones in moderate to good yields. This approach serves as a direct and site-selective strategy for the introduction of a fluorine atom at

  报道了使用 Selectfluor® 作为氟源对对康酸进行银 (I) 介导的脱羧氟化。容易获得的对康酸通过 Selectfluor® 在 AgNO3 介导下进行脱羧氟化，以中等至良好的产率得到相应的 β-氟化 γ-丁内酯。这种方法可作为在 γ-丁内酯核的 β 位置引入氟原子的直接和位点选择性策略。氟化产物是合成有用的有机合成支架。
• Fluorolactonization of unsaturated carboxylic acids with F-TEDA-BF4 in ionic liquids
  作者：Yurii A. Serguchev、Lyudmila F. Lourie、Maxim V. Ponomarenko、Eduard B. Rusanov、Nikolai V. Ignat’ev

  DOI：10.1016/j.tetlet.2011.07.124

  日期：2011.10

  Fluorolactonization of unsaturated carboxylic acids under action of the electrophilic reagent F-TEDA-BF4 in ionic liquids (ILs) has been studied. This reaction proceeds in ILs faster and provides a better stereoselectivity in comparison to acetonitrile as reaction media. Gem-difluorinated gamma-lactones have been synthesized by interaction of unsaturated carboxylic acids with F-TEDA-BF4 in ILs. (C) 2011 Elsevier Ltd. All rights reserved.