1-benzyl-3,4-bis(2-isopropylphenyl)-1H-pyrrole-2,5-dione | 1429862-81-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-benzyl-3,4-bis(2-isopropylphenyl)-1H-pyrrole-2,5-dione
• 英文别名: 1-Benzyl-3,4-bis(2-propan-2-ylphenyl)pyrrole-2,5-dione；1-benzyl-3,4-bis(2-propan-2-ylphenyl)pyrrole-2,5-dione
• CAS: 1429862-81-6
• 化学式: C₂₉H₂₉NO₂
• 分子量: 423.555
• InChiKey: FMSZHNQVNRCTBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-异丙基苯硼酸 、 N-苄基-2,3-二溴马来酰亚胺 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 以27%的产率得到1-benzyl-3-bromo-4-(2-isopropylphenyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Atropisomers of Arylmaleimides: Stereodynamics and Absolute Configuration

  摘要：

  4-Aryl-3-bromo-N-benzylmaleimides and 3,4-biaryl-N-benzylmaleimides have been synthesized by a modified Suzuki cross-coupling reaction from 3,4-dibromo-N-benzylmaleimide. The conformational studies by dynamic NMR and DFT calculations showed that the interconversion barrier between the two available skewed conformations is under steric control. When the aryl group was a 2-methylnaphthyl, thermally stable atropisomers were isolated by enantioselective HPLC and their absolute configurations were assigned by TD-DFT simulations of the ECD spectra.

  DOI：

  10.1021/jo400200v

文献信息

• Atropisomers of Arylmaleimides: Stereodynamics and Absolute Configuration
  作者：Martina Ambrogi、Alessia Ciogli、Michele Mancinelli、Silvia Ranieri、Andrea Mazzanti

  DOI：10.1021/jo400200v

  日期：2013.4.19

  4-Aryl-3-bromo-N-benzylmaleimides and 3,4-biaryl-N-benzylmaleimides have been synthesized by a modified Suzuki cross-coupling reaction from 3,4-dibromo-N-benzylmaleimide. The conformational studies by dynamic NMR and DFT calculations showed that the interconversion barrier between the two available skewed conformations is under steric control. When the aryl group was a 2-methylnaphthyl, thermally stable atropisomers were isolated by enantioselective HPLC and their absolute configurations were assigned by TD-DFT simulations of the ECD spectra.