bis(2,2,2-trifluoroethyl) 2-(2-(1,3-dioxoisoindolin-2-yl)-2-(1-methyl-1H-indol-3-yl)ethyl)malonate | 1446103-19-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: bis(2,2,2-trifluoroethyl) 2-(2-(1,3-dioxoisoindolin-2-yl)-2-(1-methyl-1H-indol-3-yl)ethyl)malonate
• 英文别名: bis(2,2,2-trifluoroethyl) 2-[2-(1,3-dioxoisoindol-2-yl)-2-(1-methylindol-3-yl)ethyl]propanedioate
• CAS: 1446103-19-0
• 化学式: C₂₆H₂₀F₆N₂O₆
• 分子量: 570.445
• InChiKey: ODMORCNRNWBOAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  94.9
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  bis(2,2,2-trifluoroethyl) 2-(2-(1,3-dioxoisoindolin-2-yl)-2-(1-methyl-1H-indol-3-yl)ethyl)malonate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以69%的产率得到dimethyl 2-(2-(1,3-dioxoisoindolin-2-yl)-2-(1-methyl-1H-indol-3-yl)ethyl)malonate
  参考文献：
  名称：

  Catalytic Friedel–Crafts Reaction of Aminocyclopropanes

  摘要：

  A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups and substitution patterns. In the case of C3-substituted indoles, C2 alkylation was observed. The reaction gives a rapid access to gamma amino acid derivatives present in numerous bioactive molecules.

  DOI：

  10.1021/ol401616a
• 作为产物：
  描述：

  bis(2,2,2-trifluoroethyl) 2-diazomalonate 在 bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 bis(2,2,2-trifluoroethyl) 2-(2-(1,3-dioxoisoindolin-2-yl)-2-(1-methyl-1H-indol-3-yl)ethyl)malonate
  参考文献：
  名称：

  Catalytic Friedel–Crafts Reaction of Aminocyclopropanes

  摘要：

  A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups and substitution patterns. In the case of C3-substituted indoles, C2 alkylation was observed. The reaction gives a rapid access to gamma amino acid derivatives present in numerous bioactive molecules.

  DOI：

  10.1021/ol401616a