1-benzyl-3-bromo-4-(2-methylnaphthalen-1-yl)-1H-pyrrole-2,5-dione | 1429862-77-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-benzyl-3-bromo-4-(2-methylnaphthalen-1-yl)-1H-pyrrole-2,5-dione
• 英文别名: 1-Benzyl-3-bromo-4-(2-methylnaphthalen-1-yl)pyrrole-2,5-dione；1-benzyl-3-bromo-4-(2-methylnaphthalen-1-yl)pyrrole-2,5-dione
• CAS: 1429862-77-0
• 化学式: C₂₂H₁₆BrNO₂
• 分子量: 406.279
• InChiKey: XAYSITWNPVCNKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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-甲基萘-1-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， 反应 2.0h， 以13%的产率得到1-benzyl-3-bromo-4-(2-methylnaphthalen-1-yl)-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.