2-(1-benzyl-2-oxo-3-phenylindolin-3-yl)acetonitrile | 1221594-22-4

• 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: 2-(1-benzyl-2-oxo-3-phenylindolin-3-yl)acetonitrile
• 英文别名: 2-(1-Benzyl-2-oxo-3-phenylindol-3-yl)acetonitrile；2-(1-benzyl-2-oxo-3-phenylindol-3-yl)acetonitrile
• CAS: 1221594-22-4
• 化学式: C₂₃H₁₈N₂O
• 分子量: 338.409
• InChiKey: JOEXYJPHAKCBAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-benzyl(2-(1-phenylvinyl)phenyl)carbamoyl cyanide 在 三乙胺 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 tri tert-butylphosphoniumtetrafluoroborate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 0.25h， 以100%的产率得到2-(1-benzyl-2-oxo-3-phenylindolin-3-yl)acetonitrile
  参考文献：
  名称：

  Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation

  摘要：

  The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.073

文献信息

• Cyanomethylation of Substituted Fluorenes and Oxindoles with Alkyl Nitriles
  作者：Gang Hong、Pradip D. Nahide、Marisa C. Kozlowski

  DOI：10.1021/acs.orglett.0c00160

  日期：2020.2.21

  cyanomethylenation from alkyl nitriles of sp3 C–H bonds to afford quaternary carbon centers is described. This oxidative protocol is operationally simple and features good functional group compatibility. This method provides a novel approach to highly functionalized fluorene and oxindole derivatives, which are commonly used in material and pharmaceutical areas. Control experiments provide evidence of a radical

  描述了从sp 3 C–H键的烷基腈产生季碳中心的无金属氰基甲基化的第一个例子。该氧化方案操作简单，并具有良好的官能团相容性。这种方法为高度官能化的芴和羟吲哚衍生物提供了一种新颖的方法，它们通常用于材料和制药领域。对照实验提供了自由基反应过程的证据。
• Synthesis of 3,3-disubstituted oxindoles through Pd-catalyzed intramolecular cyanoamidation
  作者：Yoshizumi Yasui、Haruhi Kamisaki、Takayuki Ishida、Yoshiji Takemoto

  DOI：10.1016/j.tet.2010.01.073

  日期：2010.3

  The cyanoamidation of olefins was achieved. When N-(2-vinylphenyl)cyanoformamides were treated with palladium catalyst, intramolecular cyanoamidation took place to give corresponding 3,3-disubstituted oxindoles. P(t-Bu)(3) showed a remarkable effect on this reaction. When it was used with Pd(dba)(2), the reaction was completed in 15 min at 100 degrees C for many substrates. Furthermore, the enantioselective cyanoamidation was accomplished with Pd(dba)(2) and an optically active phosphoramidite to provide optically active 3,3-disubstituted oxindoles. Manipulation of the resulting oxindoles has been studied. (C) 2010 Elsevier Ltd. All rights reserved.