(-)-3-(2-fluorophenyl)-1-methyl-2,5-pyrrolidinedione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (-)-3-(2-fluorophenyl)-1-methyl-2,5-pyrrolidinedione
• 英文别名: (3R)-3-(2-fluorophenyl)-1-methylpyrrolidine-2,5-dione
• 化学式: C₁₁H₁₀FNO₂
• 分子量: 207.204
• InChiKey: AUSSPKJOGIWNSL-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 2-氟苯硼酸 在 [Rh(OH)(cod)]2 、 (R)-MeO-F₁₂-BIPHEP 作用下， 以 乙醚 、 水 为溶剂， 反应 24.0h， 以99%的产率得到(-)-3-(2-fluorophenyl)-1-methyl-2,5-pyrrolidinedione
  参考文献：
  名称：

  Low-Temperature Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds

  摘要：

  Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds was achieved at temperatures below 0 degrees C using a Rh/MeO-F-12-BIPHEP catalyst. The reaction of cyclohexenone or N-R-maleimide with arylboronic acids proceeded even at -80 degrees C in the presence of the Rh catalyst. In the latter case, high enantioselectivity was observed because a low-temperature method was used, regardless of the type of substituent on maleimide.

  DOI：

  10.1021/jo4014707

文献信息

• Low-Temperature Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds
  作者：Toshinobu Korenaga、Aram Ko、Kazuaki Shimada

  DOI：10.1021/jo4014707

  日期：2013.10.4

  Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to alpha,beta-unsaturated carbonyl compounds was achieved at temperatures below 0 degrees C using a Rh/MeO-F-12-BIPHEP catalyst. The reaction of cyclohexenone or N-R-maleimide with arylboronic acids proceeded even at -80 degrees C in the presence of the Rh catalyst. In the latter case, high enantioselectivity was observed because a low-temperature method was used, regardless of the type of substituent on maleimide.