3-(2-methoxyphenyl)-1-phenyl-3-(phenylamino)propan-1-one | 1346451-21-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 3-(2-methoxyphenyl)-1-phenyl-3-(phenylamino)propan-1-one
• 英文别名: (3R)-3-anilino-3-(2-methoxyphenyl)-1-phenylpropan-1-one
• CAS: 1346451-21-5
• 化学式: C₂₂H₂₁NO₂
• 分子量: 331.414
• InChiKey: JXUKMDCVTWOJRK-HXUWFJFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-methoxychalcone 、 苯胺 在 碘代三甲硅烷 、 辛可宁 作用下， 反应 168.0h， 以99%的产率得到3-(2-methoxyphenyl)-1-phenyl-3-(phenylamino)propan-1-one
  参考文献：
  名称：

  Silicon-Based Lewis Acid Assisted Cinchona Alkaloid Catalysis: Highly Enantioselective Aza-Michael Reaction under Solvent-Free Conditions

  摘要：

  The study showed that a combination of an achiral silicon-based Lewis acid and chiral Lewis base, such as iodotrimethylsilane (TMSI) and cinchonine, generated a highly enantioselective catalyst system under solvent-free conditions which gave aromatic beta-amino ketones with up to >99% ee. Mechanistic studies demonstrate the enhanced asymmetric induction may be due to the combined and competitive activation of a carbonyl moiety of chalcone with cinchonine and the silicon-based Lewis acid in the aza-Michael reaction.

  DOI：

  10.1021/ol202803b

文献信息

• Silicon-Based Lewis Acid Assisted Cinchona Alkaloid Catalysis: Highly Enantioselective Aza-Michael Reaction under Solvent-Free Conditions
  作者：Hua-Meng Yang、Li Li、Fei Li、Ke-Zhi Jiang、Jun-Yan Shang、Guo-Qiao Lai、Li-Wen Xu

  DOI：10.1021/ol202803b

  日期：2011.12.16

  The study showed that a combination of an achiral silicon-based Lewis acid and chiral Lewis base, such as iodotrimethylsilane (TMSI) and cinchonine, generated a highly enantioselective catalyst system under solvent-free conditions which gave aromatic beta-amino ketones with up to >99% ee. Mechanistic studies demonstrate the enhanced asymmetric induction may be due to the combined and competitive activation of a carbonyl moiety of chalcone with cinchonine and the silicon-based Lewis acid in the aza-Michael reaction.