N-benzyl-N-[5-chloro-2-(prop-1-en-2-yl)phenyl]-1-cyanoformamide | 1042150-60-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzyl-N-[5-chloro-2-(prop-1-en-2-yl)phenyl]-1-cyanoformamide
• 英文别名: N-benzyl-N-(5-chloro-2-prop-1-en-2-ylphenyl)-1-cyanoformamide
• CAS: 1042150-60-6
• 化学式: C₁₈H₁₅ClN₂O
• 分子量: 310.783
• InChiKey: AYBIGUACWTZKRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-N-[5-chloro-2-(prop-1-en-2-yl)phenyl]-1-cyanoformamide 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86%的产率得到2-(1-benzyl-6-chloro-3-methyl-2-oxoindolin-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
• 作为产物：
  描述：

  羰基二氰化物 、 N-benzyl-5-chloro-2-(prop-1-en-2-yl)aniline 以 乙醚 为溶剂， 反应 1.0h， 以397 mg的产率得到N-benzyl-N-[5-chloro-2-(prop-1-en-2-yl)phenyl]-1-cyanoformamide
  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

• Enantioselective Synthesis of 3,3-Disubstituted Oxindoles through Pd-Catalyzed Cyanoamidation
  作者：Yoshizumi Yasui、Haruhi Kamisaki、Yoshiji Takemoto

  DOI：10.1021/ol801168j

  日期：2008.8.7

  The first enantioselective cyanoamidation of olefins provides quick access to a variety of 3,3-disubstituted oxindoles. The combination of Pd(dba)(2), an optically active phosphoramidite, and N,N-dimethylpropylene urea (DMPU) in decalin were found to be the best conditions.