3-methyl-3-(phenylamino)indolin-2-one | 1396629-21-2

• 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-methyl-3-(phenylamino)indolin-2-one
• 英文别名: 3-methyl-3-(phenylamino)indolin-2-on
• CAS: 1396629-21-2
• 化学式: C₁₅H₁₄N₂O
• 分子量: 238.289
• InChiKey: HJJYXERJRUDZPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.97
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  41.13
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-nitrophenyl trifluoromethanesulfonate 在 tetrakis(acetonitrile)palladium(II) bis(tetrafluoroborate) 、 铁粉 、 碳酸氢钠 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 氯仿 、 甲苯 为溶剂， 反应 48.0h， 生成 3-methyl-3-(phenylamino)indolin-2-one
  参考文献：
  名称：

  Synthesis of Enantiomerically Enriched 3-Amino-2-oxindoles through a Palladium-Mediated Asymmetric Intramolecular Arylation of α-Ketimino Amides

  摘要：

  A highly efficient and enantioselective synthesis of 3-amino-2-oxindoles through a palladium-catalyzed asymmetric intramolecular arylation of alpha-ketimino amides using (R)-DiFluorPhos as the coordinating ligand is reported. This report constitutes the first enantioselective palladium. catalyzed arylation of ketimines.

  DOI：

  10.1021/ol302119j

文献信息

• A direct and efficient 3-halooxidation of indoles using DMSO as oxygen source
  作者：Tao Zheng、Zhiqun Li、Yuling Luo、Jingjie Zhang、Jun Xu

  DOI：10.1016/j.tet.2023.133274

  日期：2023.3

  3-halooxidation of indoles using DMSO as the oxygen source and NXS (X = Br, Cl) the halo source. This protocol features broad substrate scope and good to excellent yields, thus rendering it as a highly versatile, straightforward, and atom-economical alternative prior to the previously reported methods, which possess their capability to undergo the SN1 substitution of a highly reactive electrophilic o-azaxylylene

  在这里，我们开发了一种直接有效的协议，用于使用 DMSO 作为氧源和 NXS（X = Br，Cl）作为晕源对吲哚进行 3-卤氧化。该协议具有广泛的底物范围和优良的产量，因此使其成为一种高度通用、直接且原子经济的替代方案，优于先前报道的方法，这些方法具有进行高反应性亲电子物质的 S N 1 取代的能力o -azaxylene中间体生成3, 3-二取代羟吲哚。
• 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.
• Fe-Catalyzed Direct α C–H Amination of Carbonyl Compounds
  作者：Siva Murru、Charles Seth Lott、Frank R. Fronczek、Radhey S. Srivastava

  DOI：10.1021/acs.orglett.5b00710

  日期：2015.5.1

  A direct Fe-catalyzed alpha-amination of 1,3-dicarbonyl compounds :has been accomplished using, arylhydroxylamines as aminating agents, This novel protocol allows convenient access to alpha-amino carbonyl derivatives without the need for any postreaction manipulations. This is an operationally simple procedure that works at low temperatures in shorter reaction times and produces high yields with excellent N-selectivity.