1-benzyl-3-methyl-3-(phenylamino)indolin-2-one | 1269105-91-0

• 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: 1-benzyl-3-methyl-3-(phenylamino)indolin-2-one
• 英文别名: 1,3-Dihydro-3-methyl-3-(phenylamino)-1-(phenylmethyl)-2H-indol-2-one；3-anilino-1-benzyl-3-methylindol-2-one
• CAS: 1269105-91-0
• 化学式: C₂₂H₂₀N₂O
• 分子量: 328.414
• InChiKey: BBPNSJWFPMRUHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-benzyl-3-(hydroxy(phenyl)amino)-3-methylindolin-2-one 在 溶剂黄146 、 锌 作用下， 反应 8.0h， 以89%的产率得到1-benzyl-3-methyl-3-(phenylamino)indolin-2-one
  参考文献：
  名称：

  Asymmetric organocatalytic N-nitroso-aldol reaction of oxindoles

  摘要：

  An organocatalytic enantioselective N-nitroso-aldol reaction of 2-oxindoles promoted by a cinchona alkaloid catalyst has been developed. The reaction shows exclusively N-selectivity, affording corresponding products with good to excellent yields (up to 100%) and moderate enantioselectivity. The regioselectivity of nitroso-aldol reaction being controlled by different cinchona catalysts was also observed. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.002

文献信息

• Synthesis of 3,3-disubstituted oxindoles by one-pot integrated Brønsted base-catalyzed trichloroacetimidation of 3-hydroxyoxindoles and Brønsted acid-catalyzed nucleophilic substitution reaction
  作者：Cyril Piemontesi、Qian Wang、Jieping Zhu

  DOI：10.1039/c2ob27196f

  日期：——

  Treatment of 3-hydroxyoxindoles with trichloroacetonitrile (1.3 equiv.) and a catalytic amount of DBU (0.1 equiv.) followed by addition of nucleophiles (1.5 equiv.) and diphenylphosphoric acid (0.2 equiv.) afforded the 3,3-disubstituted oxindoles in good to excellent yields. DFT computations supported the notion that the reaction went through the 1-alkyl-2-oxo-2H-indol-1-ium intermediate.

  用三氯乙腈（1.3 个等量物）和催化量的 DBU（0.1 个等量物）处理 3- 羟基吲哚，然后加入亲核物（1.5 个等量物）和二苯基磷酸（0.2 个等量物），可以得到 3,3-二取代的吲哚，收率从良好到极佳。DFT 计算证明，反应是通过 1-烷基-2-氧代-2H-吲哚-1-鎓中间体进行的。
• Asymmetric organocatalytic N-nitroso-aldol reaction of oxindoles
  作者：Tao Zhang、Liang Cheng、Li Liu、Dong Wang、Yong-Jun Chen

  DOI：10.1016/j.tetasy.2010.11.002

  日期：2010.12

  An organocatalytic enantioselective N-nitroso-aldol reaction of 2-oxindoles promoted by a cinchona alkaloid catalyst has been developed. The reaction shows exclusively N-selectivity, affording corresponding products with good to excellent yields (up to 100%) and moderate enantioselectivity. The regioselectivity of nitroso-aldol reaction being controlled by different cinchona catalysts was also observed. (C) 2010 Elsevier Ltd. All rights reserved.