5-chloro-2-methyl-2-phenyl-1,2-dihydro-indol-3-one | 28586-82-5

• 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: 5-chloro-2-methyl-2-phenyl-1,2-dihydro-indol-3-one
• 英文别名: 5-chloro-2-methyl-2-phenyl-1H-indol-3-one
• CAS: 28586-82-5
• 化学式: C₁₅H₁₂ClNO
• 分子量: 257.719
• InChiKey: OVCJRFWCPLRRAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-chloro-2-methyl-2-phenyl-1,2-dihydro-indol-3-one 在 四丁基高氯酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-methyl-2-phenyl-1,2-dihydro-3H-indol-3-one
  参考文献：
  名称：

  Berti, Corrado; Greci, Lucedio; Marchetti, Leonardo, Journal of Chemical Research, Miniprint, 1981, # 11, p. 3944 - 3965

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methyl-2-phenyl-1,2-dihydro-3H-indol-3-one 在 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以100%的产率得到5-chloro-2-methyl-2-phenyl-1,2-dihydro-indol-3-one
  参考文献：
  名称：

  Reactions of 1,2-Dihydro-2-methyl-2-phenyl-3H-indole-3-one with Various Halogenating Reagents.

  摘要：

  1,2-Dihydro-2-methyl-2-phenyl-3H-indole-(indoxyl) undergoes halogenation with N-chloro- and N-bromosuccinimide and N-chlorobenzotriazole forming 5- and/or 7-halogenated indoxyls. Initial one-electron transfer could be ruled out, and the reaction seems to occur either by an electrophilic aromatic substitution process or by the intermediate formation of N-haloindoxyl, which rearranges via a nitrenium ion to the reaction products. Tn experiments with I-2/AgClO4, FeCl3, Ar3NSbCl6/Bu4NCl, where the radical cation is really formed, 5,5'-dimers and halogenated dimers were always obtained together with halogenated monomers. In the reaction with CuCl2 only the 5-substituted monomer was obtained.

  DOI：

  10.3891/acta.chem.scand.52-0137

文献信息

• Acid treatment of 2-methyl-2-phenyl-3-oxo-indolin-1-oxyl
  作者：L. Greci

  DOI：10.1016/s0040-4020(01)91844-7

  日期：1983.1
• GRECI, L., TETRAHEDRON, 1983, 39, N 4, 677-681
  作者：GRECI, L.

  DOI：——

  日期：——
• Berti, Corrado; Greci, Lucedio; Marchetti, Leonardo, Journal of Chemical Research, Miniprint, 1981, # 11, p. 3944 - 3965
  作者：Berti, Corrado、Greci, Lucedio、Marchetti, Leonardo、Andruzzi, Romano、Trazza, Antonio

  DOI：——

  日期：——
• Reactions of 1,2-Dihydro-2-methyl-2-phenyl-3H-indole-3-one with Various Halogenating Reagents.
  作者：Patricia Carloni、Elisabetta Damiani、Lucedio Greci、Pierluigi Stipa、Giovanni V. Sebastiani、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0137

  日期：——

  1,2-Dihydro-2-methyl-2-phenyl-3H-indole-(indoxyl) undergoes halogenation with N-chloro- and N-bromosuccinimide and N-chlorobenzotriazole forming 5- and/or 7-halogenated indoxyls. Initial one-electron transfer could be ruled out, and the reaction seems to occur either by an electrophilic aromatic substitution process or by the intermediate formation of N-haloindoxyl, which rearranges via a nitrenium ion to the reaction products. Tn experiments with I-2/AgClO4, FeCl3, Ar3NSbCl6/Bu4NCl, where the radical cation is really formed, 5,5'-dimers and halogenated dimers were always obtained together with halogenated monomers. In the reaction with CuCl2 only the 5-substituted monomer was obtained.