(3S,4R)-3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)-butan-2-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (3S,4R)-3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)-butan-2-one
• 英文别名: (3S,4R)-3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)butan-2-one；4-[(1R,2S)-2-hydroxy-1-(4-methoxyanilino)-3-oxobutyl]benzonitrile
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: LGVDUAHISOCZRI-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 羟基丙酮 、 4-氰基苯甲醛 在 水 、 1-ethyl-3-methylimidazolium (S)-2-pyrrolidinecarboxylic acid salt 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 以97%的产率得到(3S,4R)-3-hydroxy-4-(4-methoxyphenylamino)-4-(4-cyanophenyl)-butan-2-one
  参考文献：
  名称：

  2-吡咯烷羧酸离子液体作为不对称单锅曼尼希反应的高效有机催化剂

  摘要：

  已经开发了一种使用 [EMIm][Pro] (1) 作为催化剂的新型一锅三组分不对称曼尼希反应。通过采用这种新的反应系统，合成了多种光学活性 β-氨基羰基化合物，产率高达 99%，高达 >99 dr 和 >99% ee。优化了反应条件并讨论了不对称诱导的机制。

  DOI：

  10.1002/ejoc.200901088

文献信息

• Organocatalytic, Asymmetric, One-Pot, Three-Component Mannich Reaction of Hydroxyacetone
  作者：Qing Gu、Ling-Xia Jiang、Kui Yuan、Lei Zhang、Xin-Yan Wu

  DOI：10.1080/00397910802323098

  日期：2008.11.3

  Abstract The direct three-component asymmetric Mannich reactions of hydroxyacetone with anilines and aromatic aldehydes in the presence of (2S,5S)-5-(methoxycarbonyl)pyrrolidine-2-carboxylic acid afforded syn-1,2-amino alcohols in good-to-excellent yields (55∼91%) and up to 98% ee.

  摘要 在 (2S,5S)-5-(甲氧基羰基)吡咯烷-2-羧酸存在下，羟基丙酮与苯胺和芳香醛的直接三组分不对称曼尼希反应得到了顺式 1,2-氨基醇。 - 优异的产率（55∼91%）和高达 98% ee。
• 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。
• Efficient catalysts for asymmetric Mannich reactions
  作者：Michał Rachwalski、Tim Leenders、Sylwia Kaczmarczyk、Piotr Kiełbasiński、Stanisław Leśniak、Floris P. J. T. Rutjes

  DOI：10.1039/c3ob40681d

  日期：——

  Efficient chiral catalysts for direct asymmetric three-component Mannich reactions of ketones, aldehydes and an amine (p-anisidine) have been developed. The corresponding β-amino carbonyl compounds (Mannich adducts) were obtained in good chemical yields and excellent enantio- and diastereoselectivities. The reaction conditions have been optimized by invoking ultrasonication and the influence of some structural moieties of the catalysts on the chemical yield and stereoselectivity of the Mannich products has been evaluated.

  针对酮、醛和胺（对甲氧基苯胺）的直接不对称三组分曼尼希反应开发了高效手性催化剂。获得了相应的 β-氨基羰基化合物（曼尼希加合物），化学收率高，对映和非对映选择性极佳。通过使用超声波对反应条件进行了优化，并评估了催化剂的某些结构分子对曼尼希产物的化学收率和立体选择性的影响。
• Proline catalyzed two-component, three-component and self-asymmetric Mannich reactions promoted by ultrasonic conditions
  作者：M. Lakshmi Kantam、Ch.V. Rajasekhar、G. Gopikrishna、K. Rajender Reddy、B.M. Choudary

  DOI：10.1016/j.tetlet.2006.06.042

  日期：2006.8

  The proline catalyzed two-component and three-component asymmetric Mannich reaction with hydroxyacetone and self-Mannich reaction with propanal were performed successfully under ultrasonic conditions in I It to afford Mannich products in 90-98% isolated yields and 81-99% ees with excellent diastereoselectivities. (c) 2006 Elsevier Ltd. All rights reserved.
• 2-Pyrrolidinecarboxylic Acid Ionic Liquid as a Highly Efficient Organocatalyst for the Asymmetric One-Pot Mannich Reaction
  作者：Xin Zheng、Yun-Bo Qian、Yongmei Wang

  DOI：10.1002/ejoc.200901088

  日期：2010.1

  A novel one-pot three-component asymmetric Mannich reaction using [EMIm][Pro] (1) as a catalyst has been developed. By employing this new reaction system, a variety of optically active β-amino carbonyl compounds were synthesized in up to 99 % yield with up to >99 dr and >99 % ee. The reaction conditions have been optimized and the mechanism for the asymmetric induction is discussed.

  已经开发了一种使用 [EMIm][Pro] (1) 作为催化剂的新型一锅三组分不对称曼尼希反应。通过采用这种新的反应系统，合成了多种光学活性 β-氨基羰基化合物，产率高达 99%，高达 >99 dr 和 >99% ee。优化了反应条件并讨论了不对称诱导的机制。