3-allyl-3-((4-chlorophenyl)amino)indolin-2-one | 1350466-25-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-allyl-3-((4-chlorophenyl)amino)indolin-2-one
• 英文别名: 3-(4-chloroanilino)-3-prop-2-enyl-1H-indol-2-one
• CAS: 1350466-25-9
• 化学式: C₁₇H₁₅ClN₂O
• 分子量: 298.772
• InChiKey: LKFKGZBCMAWUBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-allylindolin-2-one 在 N-溴代丁二酰亚胺(NBS) 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 3-allyl-3-((4-chlorophenyl)amino)indolin-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines

  摘要：

  AbstractA chiral N,N′‐dioxide‐nickel(II) complex‐catalyzed asymmetric amination of 3‐bromo‐3‐substituted oxindoles with anilines has been developed. A series of alkyl or aryl 3‐amino‐indolinones with quaternary stereocenters were obtained in high yields with excellent ee values in one step (up to 99 % yield, up to 96 % ee). The method provided a ready route to optically active intermediates of 3‐amino‐2‐oxindole‐based bioactive compounds. Moreover, a possible transition‐state model is proposed so as to elucidate the origin of the chirality based on the X‐ray crystal structure of the catalyst and the adduct.

  DOI：

  10.1002/chem.202100829

文献信息

• A Hg(ClO₄)₂·3H₂O Catalyzed Sakurai–Hosomi Allylation of Isatins and Isatin Ketoimines Using Allyltrimethylsilane
  作者：Zhong-Yan Cao、Yan Zhang、Cong-Bin Ji、Jian Zhou

  DOI：10.1021/ol202705g

  日期：2011.12.16

  It is reported that Hg(ClO4)(2)center dot 3H(2)O could efficiently activate the cheap but less reactive allyltrimethylsilane for the allylation of isatins or isatin ketoimines, with catalyst loading down to 0.1 mol %. This is the first example of Sakurai-Hosomi allylation of ketoimines using allyltrimethylsilane. A rare example of chiral mercury catalysis is also reported.
• Enantioselective Synthesis of 3‐Substituted 3‐Amino‐2‐oxindoles by Amination with Anilines
  作者：Wenkun Yang、Pei Dong、Jian Xu、Jian Yang、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.202100829

  日期：2021.6.25

  AbstractA chiral N,N′‐dioxide‐nickel(II) complex‐catalyzed asymmetric amination of 3‐bromo‐3‐substituted oxindoles with anilines has been developed. A series of alkyl or aryl 3‐amino‐indolinones with quaternary stereocenters were obtained in high yields with excellent ee values in one step (up to 99 % yield, up to 96 % ee). The method provided a ready route to optically active intermediates of 3‐amino‐2‐oxindole‐based bioactive compounds. Moreover, a possible transition‐state model is proposed so as to elucidate the origin of the chirality based on the X‐ray crystal structure of the catalyst and the adduct.