1-(4-methoxyphenyl)-3-(phenylamino)-3-p-tolylpropan-1-one | 287961-67-5

• 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: 1-(4-methoxyphenyl)-3-(phenylamino)-3-p-tolylpropan-1-one
• 英文别名: Propan-1-one, 1-(4-methoxyphenyl)-3-(4-methylphenyl)-3-phenylamino-；3-anilino-1-(4-methoxyphenyl)-3-(4-methylphenyl)propan-1-one
• CAS: 287961-67-5
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: HTZCBYCXFPXQEN-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：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  4'-methoxy-4-methylchalcone 、 苯胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 生成 1-(4-methoxyphenyl)-3-(phenylamino)-3-p-tolylpropan-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.