[3,3-dimethyl-2-(naphthalen-2-yloxy)indolin-1-yl](3-tolyl)methanone | 1174373-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: [3,3-dimethyl-2-(naphthalen-2-yloxy)indolin-1-yl](3-tolyl)methanone
• CAS: 1174373-04-6
• 化学式: C₂₈H₂₅NO₂
• 分子量: 407.512
• InChiKey: FFPWNTNSMBQMRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  31.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  29.54
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-萘酚 、 (2-hydroxy-3,3-dimethyl-2,3-dihydroindol-1-yl)-m-tolylmethanone 在 三氟化硼乙醚 作用下， 以 乙醚 为溶剂， 反应 3.0h， 以13%的产率得到[3,3-dimethyl-2-(naphthalen-2-yloxy)indolin-1-yl](3-tolyl)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