N-benzyl(2-(1-phenylvinyl)phenyl)carbamoyl cyanide | 1221594-05-3

• 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(2-(1-phenylvinyl)phenyl)carbamoyl cyanide
• 英文别名: N-benzyl-1-cyano-N-[2-(1-phenylethenyl)phenyl]formamide
• CAS: 1221594-05-3
• 化学式: C₂₃H₁₈N₂O
• 分子量: 338.409
• InChiKey: ATKWBGFKCGPBFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.04
• 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(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
• 作为产物：
  描述：

  羰基二氰化物 、 N-benzyl-2-(1-phenylvinyl)aniline 以 乙醚 为溶剂， 反应 1.0h， 以4.54 g的产率得到N-benzyl(2-(1-phenylvinyl)phenyl)carbamoyl cyanide
  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

• RETRACTED: Catalytic C–CN activation and asymmetric cyanoamidation of alkenes: total syntheses of (+)-horsfiline, (−)-coerulescine, and (−)-esermethole
  作者：Venkata Jaganmohan Reddy、Christopher J. Douglas

  DOI：10.1016/j.tet.2010.02.096

  日期：2010.6

  This article has been retracted: please see Elsevier Policy on Article Withdrawal (http://www.elsevier.com/locate/withdrawalpolicy). This article has been retracted at the request of the author. The author has discovered some irregularities in unpublished data related to the chemistry described in this paper. This discovery prompted the author to conduct a thorough review of the above manuscript. As

  本文已被撤消：请参阅Elsevier关于文章取款的政策（http://www.elsevier.com/locate/withdrawalpolicy）。 本文已应作者要求撤回。作者发现了与本文所述化学反应有关的未发表数据中的一些不合规定之处。这一发现促使作者对上述手稿进行了全面的审查。作为这篇评论的一部分，作者和作者研究小组的现任成员通过实验检查了本文的某些工作。一些结果，特别是对映体过量值，是不可重现的。因此，作者希望撤回此出版物。
• 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.