[3,3-dimethyl-2-(4-tolyloxy)indolin-1-yl](4-nitrophenyl)methanone | 1174372-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [3,3-dimethyl-2-(4-tolyloxy)indolin-1-yl](4-nitrophenyl)methanone
• 英文别名: [3,3-dimethyl-2-(4-methylphenoxy)-2H-indol-1-yl]-(4-nitrophenyl)methanone
• CAS: 1174372-94-1
• 化学式: C₂₄H₂₂N₂O₄
• 分子量: 402.45
• InChiKey: FBACSVWSUWHKRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3,3-dimethyl-2-(4-tolyloxy)indolin-1-yl](4-nitrophenyl)methanone 在 三氟化硼乙醚 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以20%的产率得到[2-(2-hydroxy-5-methylphenyl)-3,3-dimethylindolin-1-yl](4-nitrophenyl)methanone
  参考文献：
  名称：

  Role of 2-Naphthyl Ether Intermediate in Formation of Isolable Atropisomers Derived from the Coupling Reaction of (2-Hydroxy-3,3-dimethylindolin-1-yl)(substituted Phenyl)methanones with 2-Naphthol

  摘要：

  The formation pathway of the atropisomers derived from the reaction of (2-hydroxy-3,3-dimethylindolin-1-yl)(4-substituted phenyl)methanones with 2-naphthol in the presence of BF(3)center dot Et(2)O was discussed on the basis of the isolation of the 2-naphthyl ether intermediate whose structure was determined by single crystal X-ray analysis, The results indicate that the coupling reaction proceeds through stepwise mechanism, i.e., the ether intermediate formation followed by Fries-type rearrangement.

  DOI：

  10.3987/com-09-11644
• 作为产物：
  描述：

  对甲酚 、 (2-hydroxy-3,3-dimethylindolin-1-yl)(4-nitrophenyl)methanone 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以44%的产率得到[3,3-dimethyl-2-(4-tolyloxy)indolin-1-yl](4-nitrophenyl)methanone
  参考文献：
  名称：

  Role of 2-Naphthyl Ether Intermediate in Formation of Isolable Atropisomers Derived from the Coupling Reaction of (2-Hydroxy-3,3-dimethylindolin-1-yl)(substituted Phenyl)methanones with 2-Naphthol

  摘要：

  The formation pathway of the atropisomers derived from the reaction of (2-hydroxy-3,3-dimethylindolin-1-yl)(4-substituted phenyl)methanones with 2-naphthol in the presence of BF(3)center dot Et(2)O was discussed on the basis of the isolation of the 2-naphthyl ether intermediate whose structure was determined by single crystal X-ray analysis, The results indicate that the coupling reaction proceeds through stepwise mechanism, i.e., the ether intermediate formation followed by Fries-type rearrangement.

  DOI：

  10.3987/com-09-11644