1-benzyl-5-chloro-3-hydroxy-3-[2-(4-methylphenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-benzyl-5-chloro-3-hydroxy-3-[2-(4-methylphenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one
• 英文别名: 1-benzyl-5-chloro-3-hydroxy-3-[2-(4-methylphenyl)-2-oxoethyl]indol-2-one
• 化学式: C₂₄H₂₀ClNO₃
• 分子量: 405.9
• InChiKey: HMVBOETVWBRQAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-5-chloro-3-hydroxy-3-[2-(4-methylphenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one 在 盐酸 、 4-氟苯乙酮 作用下， 以928 mg的产率得到(E)-1-benzyl-5-chloro-3-(2-oxo-2-(p-tolyl)ethylidene)indolin-2-one
  参考文献：
  名称：

  tert‐Butyl Nitrite Promoted Visible‐Light‐Induced Steric‐Hindrance‐Regulated Concurrent Cross‐Coupling and Regioselective Nitration of 3‐Alkylidene‐2‐oxindoles

  摘要：

  A tert‐butyl nitrite (TBN) promoted visible‐light‐induced one‐pot C−N cross coupling reaction of 3‐alkylidene‐2‐oxindoles with benzene‐1,2‐diamine was explored. Simultaneously, the indoline motif of 3‐alkylidene‐2‐oxindoles as well as 3‐ylidene oxindoles are regioselectively nitrated at the C‐6 position by in‐situ formed NO₂ radical. (E)‐3‐(2‐(aryl)‐2‐oxoethylidene)oxindole and (E)‐3‐ylidene oxindole produce distinct nitrated diastereomeric coupling products, a phenomenon influenced by the steric bulk of the functional group. The experimental findings suggest the potential involvement of a radical pathway in this reaction.

  DOI：

  10.1002/adsc.202301159
• 作为产物：
  描述：

  1-benzyl-5-chloroisatin 、 对甲基苯乙酮 在 三乙胺 作用下， 以 乙醇 为溶剂， 生成 1-benzyl-5-chloro-3-hydroxy-3-[2-(4-methylphenyl)-2-oxoethyl]-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  tert‐Butyl Nitrite Promoted Visible‐Light‐Induced Steric‐Hindrance‐Regulated Concurrent Cross‐Coupling and Regioselective Nitration of 3‐Alkylidene‐2‐oxindoles

  摘要：

  A tert‐butyl nitrite (TBN) promoted visible‐light‐induced one‐pot C−N cross coupling reaction of 3‐alkylidene‐2‐oxindoles with benzene‐1,2‐diamine was explored. Simultaneously, the indoline motif of 3‐alkylidene‐2‐oxindoles as well as 3‐ylidene oxindoles are regioselectively nitrated at the C‐6 position by in‐situ formed NO₂ radical. (E)‐3‐(2‐(aryl)‐2‐oxoethylidene)oxindole and (E)‐3‐ylidene oxindole produce distinct nitrated diastereomeric coupling products, a phenomenon influenced by the steric bulk of the functional group. The experimental findings suggest the potential involvement of a radical pathway in this reaction.

  DOI：

  10.1002/adsc.202301159

文献信息

• <i>tert</i>‐Butyl Nitrite Promoted Visible‐Light‐Induced Steric‐Hindrance‐Regulated Concurrent Cross‐Coupling and Regioselective Nitration of 3‐Alkylidene‐2‐oxindoles
  作者：Prabhat Sarkar、Soumitra Rana、Debashis Jana、Subham Mandal、Chhanda Mukhopadhyay

  DOI：10.1002/adsc.202301159

  日期：2024.4.9

  A tert‐butyl nitrite (TBN) promoted visible‐light‐induced one‐pot C−N cross coupling reaction of 3‐alkylidene‐2‐oxindoles with benzene‐1,2‐diamine was explored. Simultaneously, the indoline motif of 3‐alkylidene‐2‐oxindoles as well as 3‐ylidene oxindoles are regioselectively nitrated at the C‐6 position by in‐situ formed NO₂ radical. (E)‐3‐(2‐(aryl)‐2‐oxoethylidene)oxindole and (E)‐3‐ylidene oxindole produce distinct nitrated diastereomeric coupling products, a phenomenon influenced by the steric bulk of the functional group. The experimental findings suggest the potential involvement of a radical pathway in this reaction.