1-benzyl-N²,N⁴-bis(2-chlorophenyl)-2,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrrole-2,4-dicarboxamide | 1002555-80-7

• 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-N²,N⁴-bis(2-chlorophenyl)-2,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrrole-2,4-dicarboxamide
• 英文别名: 1-benzyl-2-N,4-N-bis(2-chlorophenyl)-2,5-dimethyl-3-oxopyrrole-2,4-dicarboxamide
• CAS: 1002555-80-7
• 化学式: C₂₇H₂₃Cl₂N₃O₃
• 分子量: 508.404
• InChiKey: LURQSFRNWHQJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(benzylamino)-N-(2-chlorophenyl)but-2-enamide 在 叔丁基过氧化氢 、 氧气 、 copper(II) trifluoroacetate 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 以82%的产率得到1-benzyl-N²,N⁴-bis(2-chlorophenyl)-2,5-dimethyl-3-oxo-2,3-dihydro-1H-pyrrole-2,4-dicarboxamide
  参考文献：
  名称：

  Cu(TFA)₂-Catalyzed Oxidative Tandem Cyclization/1,2-Alkyl Migration of Enamino Amides for Synthesis of Pyrrolin-4-ones

  摘要：

  A novel Cu(TFA)(2)-catalyzed oxidative tandem cyclization/1,2-alkyl migration of readily available enamino amides for the synthesis of pyrrolin-4-ones has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of substituted pyrrolin-4-ones in high yields under mild conditions.

  DOI：

  10.1021/ol4022222

文献信息

• Efficient Synthesis of Highly Substituted Pyrrolin-4-ones via PIFA-Mediated Cyclization Reactions of Enaminones
  作者：Jie Huang、Yongjiu Liang、Wei Pan、Yang、Dewen Dong

  DOI：10.1021/ol702362n

  日期：2007.12.1

  highly substituted pyrrolin-4-ones is developed via the PIFA-mediated cyclization reactions of readily available enaminones, and a mechanism involving sequential cleavage of N-C bond, formation of new N-C bond, intramolecular addition reaction, and benzilic acid type rearrangement is proposed.

  通过PIFA介导的易获得的烯胺酮的环化反应，开发了一种便捷有效的合成高取代的吡咯啉-4-酮的方法，该机理涉及顺序裂解NC键，形成新的NC键，分子内加成反应和苯甲酸。建议进行类型重排。
• Cu(TFA)₂-Catalyzed Oxidative Tandem Cyclization/1,2-Alkyl Migration of Enamino Amides for Synthesis of Pyrrolin-4-ones
  作者：Zhi-Jing Zhang、Zhi-Hui Ren、Yao-Yu Wang、Zheng-Hui Guan

  DOI：10.1021/ol4022222

  日期：2013.9.20

  A novel Cu(TFA)(2)-catalyzed oxidative tandem cyclization/1,2-alkyl migration of readily available enamino amides for the synthesis of pyrrolin-4-ones has been developed. The reaction tolerates a wide range of functional groups and is a reliable method for the rapid synthesis of substituted pyrrolin-4-ones in high yields under mild conditions.