5,5-二氟-1-甲基-1,5-二氢-2H-吡咯-2-酮 | 363152-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 中文名称: 5,5-二氟-1-甲基-1,5-二氢-2H-吡咯-2-酮
• 英文名称: 5,5-difluoro-1-methyl-3-pyrrolin-2-one
• 英文别名: 5,5-Difluoro-1-methyl-1H-pyrrol-2(5H)-one；5,5-difluoro-1-methylpyrrol-2-one
• CAS: 363152-96-9
• 化学式: C₅H₅F₂NO
• mdl: MFCD09032482
• 分子量: 133.098
• InChiKey: QNJBYLBXSZUFEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  2,5,5-三氟-1-甲基-2,5-二氢-1H-吡咯-2-甲腈 在 水 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以83%的产率得到5,5-二氟-1-甲基-1,5-二氢-2H-吡咯-2-酮
  参考文献：
  名称：

  有机化合物的电解部分氟化。第48部分：2-氰基-1-甲基吡咯的阳极氟化

  摘要：

  在未分格的电池中使用Et 3 N·2HF对2-氰基-1-甲基吡咯进行阳极氟化反应，提供了相应的5-氟吡咯和2,5,5-三氟-1-甲基-3-吡咯啉-2-腈。 Et 3 N·3HF选择性地提供了后者的产物，其易于水解为可分离的5,5-二氟-1-甲基-3-吡咯啉-2-酮。这是吡咯衍生物成功进行阳极氟化的第一份报告。

  DOI：

  10.1016/s0040-4039(01)00866-8

文献信息

• A Facile Synthesis of<i>gem</i>-Difluorinated Heterocyclic Compounds Using Anodic­ Fluorination of 2-Cyano-1-methylpyrrole as a Key Step
  作者：Toshio Fuchigami、Toshiki Tajima

  DOI：10.1055/s-2002-35621

  日期：——

  Anodic fluorination of 2-cyano-1-methylpyrrole 1 using Et3N·5HF in an undivided cell provided 5,5-difluoro-1-methyl-3-pyrrolin-2-one (5a). The Diels-Alder reaction of 5a with various dienes was successfully carried out to provide gem-difluorinated heterocyclic compounds in excellent yields.

  使用 Et3N-5HF 在不分裂电池中对 2-氰基-1-甲基吡咯 1 进行阳极氟化，得到了 5,5-二氟-1-甲基-3-吡咯啉-2-酮（5a）。成功地将 5a 与各种二烯进行了 Diels-Alder 反应，得到了产率极高的宝石二氟杂环化合物。
• 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.
• Electrolytic partial fluorination of organic compounds. Part 48: Anodic fluorination of 2-cyano-1-methylpyrrole
  作者：Toshiki Tajima、Hideki Ishii、Toshio Fuchigami

  DOI：10.1016/s0040-4039(01)00866-8

  日期：2001.7

  Anodic fluorination of 2-cyano-1-methylpyrrole using Et3N·2HF in an undivided cell provided the corresponding 5-fluoropyrrole and 2,5,5-trifluoro-1-methyl-3-pyrrolin-2-carbonitrile while the use of Et3N·3HF afforded selectively the latter product, which was readily hydrolyzed to isolable 5,5-difluoro-1-methyl-3-pyrroline-2-one. This is the first report of successful anodic fluorination of a pyrrole

  在未分格的电池中使用Et 3 N·2HF对2-氰基-1-甲基吡咯进行阳极氟化反应，提供了相应的5-氟吡咯和2,5,5-三氟-1-甲基-3-吡咯啉-2-腈。 Et 3 N·3HF选择性地提供了后者的产物，其易于水解为可分离的5,5-二氟-1-甲基-3-吡咯啉-2-酮。这是吡咯衍生物成功进行阳极氟化的第一份报告。