4-(4-ethoxyphenylamino)-5,5-difluoro-1-methylpyrrolidin-2-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(4-ethoxyphenylamino)-5,5-difluoro-1-methylpyrrolidin-2-one
• 英文别名: 4-(4-Ethoxyanilino)-5,5-difluoro-1-methylpyrrolidin-2-one
• 化学式: C₁₃H₁₆F₂N₂O₂
• 分子量: 270.279
• InChiKey: USSSDIYAPDSNKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对乙氧基苯胺 、 5,5-二氟-1-甲基-1,5-二氢-2H-吡咯-2-酮 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以80%的产率得到4-(4-ethoxyphenylamino)-5,5-difluoro-1-methylpyrrolidin-2-one
  参考文献：
  名称：

  Electrolytic Partial Fluorination of Organic Compounds. 83. Anodic Fluorination of N-Substituted Pyrroles and Its Synthetic Applications to gem-Difluorinated Heterocyclic Compounds

  摘要：

  Anodic fluorination of N-substituted pyrroles was carried out in MeCN containing supporting fluoride salts such as Et3N-nHF (n = 2-5) and Et4NF-4HF with use of platinum electrodes under constant current conditions. Anodic fluorination of N-methyl- and N-p-tosylpyrroles having an electron-withdrawing cyano group proceeded smoothly to provide the corresponding fluorinated products in moderate to excellent yields, while anodic fluorination of N-methylpyrrole devoid of an electron-withdrawing cyano group did not take place and a polymeric product was formed at the anode surface. In sharp contrast to the cases of N-methylpyrroles, even N-p-tosylpyrrole devoid of an electron-withdrawing cyano group underwent anodic fluorination efficiently. Diels-Alder reaction of 5,5-difluoro-1-methyl-3-pyrrolin-2-one (2e) derived from anodic fluorination of 2-cyano-1-methylpyrrole (2a) with various dienes was carried out to provide the cycloaddition products in excellent yields. Furthermore, Michael reaction of 2e with various nucleophiles was also successfully carried out to provide the Michael addition products in good to excellent yields.

  DOI：

  10.1021/jo0520745

文献信息

• Electrolytic Partial Fluorination of Organic Compounds. 83. Anodic Fluorination of <i>N</i>-Substituted Pyrroles and Its Synthetic Applications to <i>g</i><i>em</i>-Difluorinated Heterocyclic Compounds
  作者：Toshiki Tajima、Atsushi Nakajima、Toshio Fuchigami

  DOI：10.1021/jo0520745

  日期：2006.2.1

  Anodic fluorination of N-substituted pyrroles was carried out in MeCN containing supporting fluoride salts such as Et3N-nHF (n = 2-5) and Et4NF-4HF with use of platinum electrodes under constant current conditions. Anodic fluorination of N-methyl- and N-p-tosylpyrroles having an electron-withdrawing cyano group proceeded smoothly to provide the corresponding fluorinated products in moderate to excellent yields, while anodic fluorination of N-methylpyrrole devoid of an electron-withdrawing cyano group did not take place and a polymeric product was formed at the anode surface. In sharp contrast to the cases of N-methylpyrroles, even N-p-tosylpyrrole devoid of an electron-withdrawing cyano group underwent anodic fluorination efficiently. Diels-Alder reaction of 5,5-difluoro-1-methyl-3-pyrrolin-2-one (2e) derived from anodic fluorination of 2-cyano-1-methylpyrrole (2a) with various dienes was carried out to provide the cycloaddition products in excellent yields. Furthermore, Michael reaction of 2e with various nucleophiles was also successfully carried out to provide the Michael addition products in good to excellent yields.