(2-fluorophenyl)(1-tosyl-2,5-dihydro-1H-pyrrol-2-yl)methanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2-fluorophenyl)(1-tosyl-2,5-dihydro-1H-pyrrol-2-yl)methanone
• 化学式: C₁₈H₁₆FNO₃S
• 分子量: 345.394
• InChiKey: PISGLSQYPVRAMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2-fluorophenyl)(1-tosyl-2,5-dihydro-1H-pyrrol-2-yl)methanone 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以94%的产率得到(2-fluorophenyl)(1H-pyrrol-2-yl)methanone
  参考文献：
  名称：

  Silver(I)‐Catalyzed Conia‐Ene Reaction: Synthesis of 3‐Pyrrolines via a 5‐ endo ‐ dig Cyclization

  摘要：

  AbstractA novel method has been developed for the synthesis of 3‐pyrrolines from β‐ketopropargylamines via a 5‐endo‐dig carbocyclization. This transformation involves a silver‐catalyzed Conia‐ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2‐substituted pyrroles under base‐mediated conditions.magnified image

  DOI：

  10.1002/adsc.201300844
• 作为产物：
  描述：

  2-溴-2'-氟苯乙酮 在 silver trifluoromethanesulfonate 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 硝基甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (2-fluorophenyl)(1-tosyl-2,5-dihydro-1H-pyrrol-2-yl)methanone
  参考文献：
  名称：

  Silver(I)‐Catalyzed Conia‐Ene Reaction: Synthesis of 3‐Pyrrolines via a 5‐ endo ‐ dig Cyclization

  摘要：

  AbstractA novel method has been developed for the synthesis of 3‐pyrrolines from β‐ketopropargylamines via a 5‐endo‐dig carbocyclization. This transformation involves a silver‐catalyzed Conia‐ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2‐substituted pyrroles under base‐mediated conditions.magnified image

  DOI：

  10.1002/adsc.201300844

文献信息

• Silver(I)‐Catalyzed Conia‐Ene Reaction: Synthesis of 3‐Pyrrolines <i>via</i> a 5‐ <i>endo</i> ‐ <i>dig</i> Cyclization
  作者：Siva Senthil Kumar Boominathan、Wan‐Ping Hu、Gopal Chandru Senadi、Jeh‐Jeng Wang

  DOI：10.1002/adsc.201300844

  日期：2013.12.16

  AbstractA novel method has been developed for the synthesis of 3‐pyrrolines from β‐ketopropargylamines via a 5‐endo‐dig carbocyclization. This transformation involves a silver‐catalyzed Conia‐ene type reaction tolerating broad substrate scope with good to excellent yields. Furthermore, this methodology has been extended for the construction of 2‐substituted pyrroles under base‐mediated conditions.magnified image