(R)-1-phenyl-3-(N-phenylamino)-3-(4-tolyl)propan-1-one | 1091601-84-1

• 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: (R)-1-phenyl-3-(N-phenylamino)-3-(4-tolyl)propan-1-one
• 英文别名: 1-phenyl-3-(phenylamino)-3-p-tolylpropan-1-one；3-(4-methylphenyl)-1-phenyl-3-(phenylamino)propan-1-one；(3R)-3-anilino-3-(4-methylphenyl)-1-phenylpropan-1-one
• CAS: 1091601-84-1
• 化学式: C₂₂H₂₁NO
• 分子量: 315.415
• InChiKey: PIDZXZUXXULGNN-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 、 苯胺 在 碘代三甲硅烷 、 辛可宁 作用下， 反应 48.0h， 以99%的产率得到(R)-1-phenyl-3-(N-phenylamino)-3-(4-tolyl)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

• Organocatalytic asymmetric aza-Michael addition of aniline to chalcones under solvent-free conditions
  作者：Arrigo Scettri、Antonio Massa、Laura Palombi、Rosaria Villano、Maria Rosaria Acocella

  DOI：10.1016/j.tetasy.2008.09.006

  日期：2008.9

  The first enantioselective Michael addition of aniline to chalcones was promoted by cheap and commercially available chincona alkaloids under solvent-free conditions. Variously substituted chalcones were examined as substrates giving the conjugate adducts in moderate to good enantioselectivity. The simple experimental procedure had no work-up and short reaction times, which are the notable advantages. (C) 2008 Elsevier Ltd. All rights reserved.
• Brønsted acid catalyzed enantio- and diastereoselective one-pot three component Mannich reaction
  作者：Margherita Barbero、Silvano Cadamuro、Stefano Dughera

  DOI：10.1016/j.tetasy.2015.09.006

  日期：2015.11

  A chiral derivative of 1,2-benzenedisulfonimide,(-)-4,5-dimethy1-3,6-bis(o-toly1)-1,2-benzenedisulfonimide is herein proven to be an efficient chiral catalyst in a one pot three-component Mannich protocol. Reaction conditions are mild and green, while the enantio- and diastereoselectivity are excellent. (C) 2015 Elsevier Ltd. All rights reserved.