(S)-1-(4-methoxy-phenylamino)-1-(4-nitrophenyl)-pentan-3-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(4-methoxy-phenylamino)-1-(4-nitrophenyl)-pentan-3-one
• 英文别名: (S)-1-(4-methoxyphenylamino)-1-(4-nitrophenyl)pentan-3-one；(S)-1-(4-methoxyphenylamino)-1-(4-nitrophenyl)butan-2-one；(1S)-1-(4-methoxyanilino)-1-(4-nitrophenyl)pentan-3-one
• 化学式: C₁₈H₂₀N₂O₄
• 分子量: 328.368
• InChiKey: UHAXVDRGVVUUQI-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(4-甲氧基苯基)-1-(4-硝基苯基)甲亚胺 、 丁酮 在 1,1'-([2,2'-bipyridine]-4,4'-diyl)bis(3-(3,5-bis(trifluoro-methyl)phenyl)thiourea) 、 L-脯氨酸 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以95%的产率得到
  参考文献：
  名称：

  Study of asymmetric aldol and Mannich reactions catalyzed by proline–thiourea host–guest complexes in nonpolar solvents

  摘要：

  A proline-thiourea host-guest complex has been described as a good catalyst for asymmetric reactions such as aldol and Mannich reactions. High stereoselectivities were obtained under optimal conditions. Thiourea was observed to have an important effect on the reactivity and selectivity, even in an unconventional nonpolar reaction medium and without the need to utilize low temperatures. This proline-thiourea host-guest system has the ability to participate in a hydrogen bonding network. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.03.014

文献信息

• The Scope of the Direct Proline-Catalyzed Asymmetric Addition of Ketones to Imines
  作者：Wolfgang Notz、Shin-ichi Watanabe、Naidu S. Chowdari、Guofu Zhong、Juan M. Betancort、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1002/adsc.200404114

  日期：2004.8

  A full account of catalytic direct asymmetric Mannich-type reactions is presented describing the scope of amino acid-catalyzed additions of unmodified ketones to a large variety of imines. These reactions are performed under very mild, operationally simple, and environmentally friendly and benign conditions employing a one-pot, three-component protocol as well as preformed imines. Typically, products

  提供了催化直接不对称曼尼希型反应的完整说明，描述了氨基酸催化的未修饰酮加到各种亚胺中的范围。这些反应是在非常温和的，操作简单的，环境友好的和良性的条件下进行的，采用一锅，三组分方案以及预先形成的亚胺。通常，获得的产物具有高区域和非对映选择性以及极好的对映选择性。所开发的方法学被用作合成对映体纯的功能化α-氨基酸，γ-内酯，肟功能化氨基酸以及药理学上重要的靶标（如（R）-环己基甘氨酸）的有力方法。
• The Proline-Catalyzed Direct Asymmetric Three-Component Mannich Reaction:  Scope, Optimization, and Application to the Highly Enantioselective Synthesis of 1,2-Amino Alcohols
  作者：Benjamin List、Peter Pojarliev、William T. Biller、Harry J. Martin

  DOI：10.1021/ja0174231

  日期：2002.2.1

  We have developed proline-catalyzed direct asymmetric three-component Mannich reactions of ketones, aldehydes, and amines. Several of the studied reactions provide beta-amino carbonyl compounds (Mannich products) in excellent enantio-, diastereo-, regio-, and chemoselectivities. The scope of each of the three components and the influence of the catalyst structure on the reaction are described. Reaction

  我们开发了脯氨酸催化的酮、醛和胺的直接不对称三组分曼尼希反应。一些研究的反应提供了具有出色对映选择性、非对映选择性、区域选择性和化学选择性的 β-氨基羰基化合物（曼尼希产物）。描述了三种组分各自的范围以及催化剂结构对反应的影响。优化了反应条件，讨论了不对称诱导的机理和来源。我们进一步介绍了我们的反应在 1,2-氨基醇的高度对映选择性合成中的应用。
• Study of asymmetric aldol and Mannich reactions catalyzed by proline–thiourea host–guest complexes in nonpolar solvents
  作者：Ayhan Sıtkı Demir、Sinan Basceken

  DOI：10.1016/j.tetasy.2013.03.014

  日期：2013.4

  A proline-thiourea host-guest complex has been described as a good catalyst for asymmetric reactions such as aldol and Mannich reactions. High stereoselectivities were obtained under optimal conditions. Thiourea was observed to have an important effect on the reactivity and selectivity, even in an unconventional nonpolar reaction medium and without the need to utilize low temperatures. This proline-thiourea host-guest system has the ability to participate in a hydrogen bonding network. (C) 2013 Elsevier Ltd. All rights reserved.