3-(3-oxo-1,3-diphenylpropyl)oxazolin-2-one

• 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-(3-oxo-1,3-diphenylpropyl)oxazolin-2-one
• 英文别名: 3-(3-Oxo-1,3-diphenylpropyl)-1,3-oxazolidin-2-one
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: CFZFPXREMWXYKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-唑烷酮 、 反式-查耳酮 在 三甲基氯硅烷 、 三氯化铁 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以52%的产率得到3-(3-oxo-1,3-diphenylpropyl)oxazolin-2-one
  参考文献：
  名称：

  An efficient and inexpensive catalyst system for the aza-Michael reactions of enones with carbamatesElectronic supplementary information (ESI) available: experimental. See http://www.rsc.org/suppdata/cc/b3/b307733k/

  摘要：

  一种新的策略被开发出来，使用非常廉价的氯化铁(III)作为有效催化剂，在三甲基氯硅烷存在下，实现了酮和查尔酮与未活化的弱亲核性氨基甲酸酯的共轭加成反应。

  DOI：

  10.1039/b307733k

文献信息

• Highly Efficient Aza-Michael Reactions of Enones with Carbamates Using a Combination of Quaternary Ammonium Salts and BF₃·OEt₂as a Catalyst
  作者：Chun-Gu Xia、Li-Wen Xu、Lyi Li、Shao-Lin Zhou、Jing-Wei Li、Xiao-Xue Hu

  DOI：10.1055/s-2003-43333

  日期：——

  Aza-Michael reactions of enones with carbamates took efficiently in the presence of a catalytic amount of quaternary ammonium salts and BF 3 .OEt 2 to afford the total products in high yields. The new catalytic system was also efficient in the aza-Michael reaction of chalcone, which was difficult to react with carbamates by transition metal salts catalysts.

  烯酮与氨基甲酸酯的 Aza-Michael 反应在催化量的季铵盐和 BF 3 .OEt 2 存在下有效进行，以高产率提供总产物。新的催化体系在查尔酮的氮杂-迈克尔反应中也很有效，该反应很难通过过渡金属盐催化剂与氨基甲酸酯反应。
• TMAF-Catalyzed Conjugate Addition of Oxazolidinone and Thiols
  作者：Vincent Dalla、Mickaël Ménand

  DOI：10.1055/s-2004-836057

  日期：——

  TMAF (Me4NF) is a useful catalyst for the conjugate ­addition of oxazolidinone and thiols to a range of Michael acceptors including esters, ketones, nitroolefins and cinnamaldehyde.

  TMAF（Me4NF）是一种有用的催化剂，可用于将恶唑烷酮和硫醇加成到包括酯、酮、硝基烯烃和肉桂醛在内的一系列迈克尔受体上。
• TMSCl-Promoted Transition Metal-Catalyzed Aza-Michael Reactions of Chalcones with Carbamates
  作者：Chun-Gu Xia、Li-Wen Xu

  DOI：10.1055/s-2004-829197

  日期：——

  An improved strategy, which uses transition metals as effective catalyst in the presence of Me3SiCl, has been developed for the conjugate addition of chalcones with unactivated weakly nucleophilic carbamates.

  针对查耳酮与未活化的弱亲核氨基甲酸酯的共轭加成，开发了一种改进的策略，即在 Me3SiCl 存在下使用过渡金属作为有效催化剂。
• Highly efficient phosphine-catalyzed aza-Michael reactions of α,β-unsaturated compounds with carbamates in the presence of TMSCl
  作者：Li-Wen Xu、Chun-Gu Xia

  DOI：10.1016/j.tetlet.2004.04.053

  日期：2004.5

  Aza-Michael reactions of enones with carbamates took place efficiently in the presence of a catalytic amount of phosphine and TMSCI to afford the total products in high yields. The new catalytic system was also efficient in the aza-Michael reaction of chalcone, which was difficult to react with carbamates by transition metal salts catalysts. (C) 2004 Elsevier Ltd. All rights reserved.
• Efficient catalytic aza-Michael additions of carbamates to enones: revisited dual activation of hard nucleophiles and soft electrophiles by InCl3/TMSCl catalyst system
  作者：Lei Yang、Li-Wen Xu、Chun-Gu Xia

  DOI：10.1016/j.tetlet.2006.12.137

  日期：2007.2

  The aza-Michael reaction of a variety of chalcones with weaker nucleophilic carbamates catalyzed by InCl3 in the presence of TMSCl via the entry of dual activation of both hard nucleophiles (carbamates) and soft electrophiles (enones) to provide the corresponding adducts in good yields. The first example of enantioselective aza-Michael reaction of chalcones with carbamates was also investigated in the presence of the present catalyst system. (c) 2007 Elsevier Ltd. All rights reserved.