3-(benzyloxymethyl)-3-methyl-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)pyrrolidine-2,5-dione | 1257521-53-1

• 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-(benzyloxymethyl)-3-methyl-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)pyrrolidine-2,5-dione
• 英文别名: 3-Methyl-3-(phenylmethoxymethyl)-1-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrrolidine-2,5-dione；3-methyl-3-(phenylmethoxymethyl)-1-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrrolidine-2,5-dione
• CAS: 1257521-53-1
• 化学式: C₂₀H₁₄F₇NO₃
• 分子量: 449.325
• InChiKey: MBVVBRSQWGSHCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  一氧化碳 、 3-benzyloxy-2,2-dimethyl-N-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)propanamide 在 potassium dihydrogenphosphate 、 2,2,6,6-四甲基哌啶氧化物 、 silver(I) acetate 、 palladium diacetate 作用下， 以 正己烷 为溶剂， 130.0 ℃ 、101.33 kPa 条件下， 反应 18.0h， 以92%的产率得到3-(benzyloxymethyl)-3-methyl-1-(2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl)pyrrolidine-2,5-dione
  参考文献：
  名称：

  Pd(II)-Catalyzed Carbonylation of C(sp³)−H Bonds: A New Entry to 1,4-Dicarbonyl Compounds

  摘要：

  Pd(II)-catalyzed beta-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing alpha-hydrogen atoms and could be applied to effect methylene C(sp(3))-H carbonylation of cyclopropanes.

  DOI：

  10.1021/ja108754f

文献信息

• Pd(II)-Catalyzed Carbonylation of C(sp³)−H Bonds: A New Entry to 1,4-Dicarbonyl Compounds
  作者：Eun Jeong Yoo、Masayuki Wasa、Jin-Quan Yu

  DOI：10.1021/ja108754f

  日期：2010.12.15

  Pd(II)-catalyzed beta-C(sp(3))-H carbonylation of N-arylamides under CO (1 atm) has been achieved. Following amide-directed C(sp(3))-H cleavage and insertion of CO into the resulting [Pd(II)-C(sp(3))] bond, intramolecular C-N reductive elimination gave the corresponding succinimides, which could be readily converted to 1,4-dicarbonyl compounds. This method was found to be effective with substrates containing alpha-hydrogen atoms and could be applied to effect methylene C(sp(3))-H carbonylation of cyclopropanes.