(3R,4R)-4-(p-cyanophenyl)-1,3-dihydroxy-4-(p-methoxyphenylamino)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: (3R,4R)-4-(p-cyanophenyl)-1,3-dihydroxy-4-(p-methoxyphenylamino)butan-2-one
• 英文别名: 4-[(1R,2R)-2,4-dihydroxy-1-(4-methoxyanilino)-3-oxobutyl]benzonitrile
• 化学式: C₁₈H₁₈N₂O₄
• 分子量: 326.352
• InChiKey: UZEBAFNPYPGOSV-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1,3-二羟基丙酮 、 N-(4-甲氧基苯基)-4-氰基苯甲亚胺 在 5-甲基四氮唑 、 O-叔丁基-L-苏氨酸 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 24.0h， 生成 (3R,4R)-4-(p-cyanophenyl)-1,3-dihydroxy-4-(p-methoxyphenylamino)butan-2-one 、 、
  参考文献：
  名称：

  与二羟基丙酮和无环二羟基丙酮衍生物的有机催化抗曼尼希反应：氨基糖的简便途径。

  摘要：

  已经开发出了第一羟基含伯胺的氨基酸催化的二羟基丙酮和无环二羟基丙酮衍生物与各种亚胺的抗曼尼希反应。这种方法补充了基于脯氨酸的氨基糖制备策略。

  DOI：

  10.1002/adsc.200800069

文献信息

• Direct catalytic asymmetric three-component Mannich reactions with dihydroxyacetone: enantioselective synthesis of amino sugar derivatives
  作者：Pawel Dziedzic、Ismail Ibrahem、Armando Córdova

  DOI：10.1016/j.tetlet.2007.11.196

  日期：2008.1

  Highly enantioselective, amino acid-catalyzed, one-pot three-component asymmetric Mannich reactions between dihydroxyacetone, p-anisidine, and aldehydes are presented. The reactions proceeded with high chemo- and stereoselectivity and furnished the corresponding α,α′-dihydroxy-β-aminoketones in high yields with 82–95% ee.

  提出了在二羟基丙酮，对茴香胺和醛之间的高度对映选择性，氨基酸催化的一锅三组分不对称曼尼希反应。反应以高化学选择性和立体选择性进行，并以82-95％ee的高收率提供了相应的α，α'-二羟基-β-氨基酮。
• Continuous Flow Enantioselective Three-Component <i>anti</i>-Mannich Reactions Catalyzed by a Polymer-Supported Threonine Derivative
  作者：Carles Ayats、Andrea H. Henseler、Estefanía Dibello、Miquel A. Pericàs

  DOI：10.1021/cs5006037

  日期：2014.9.5

  A series of primary amino acid-derived polystyrene-supported organocatalysts was tested in antiselective Mannidi reactions. The polystyrene-immobilized threonine derivative showed the best performance in threecomponent (hydroxyacetone, anilines, and aldehydes) Mannich reactions to provide anti-beta-amino-alpha-hydroxycarbonyl compounds (11 examples; up to 95% ee), and its use could be extended to dihydroxyacetone and protected hydroxyace-tones (7 examples; up to 90% ee). The high activity depicted by the catalyst has allowed its implementation in continuous flow. Under this operation mode, the supported threonine catalyst produces anti-Mannich adducts with generally higher diastereo- and enantioselectivity than in batch. A family of five different enantioenriched anti-Mannich adducts has been sequentially prepared in flow by passing different combinations of anilines and aromatic aldehydes over the same sample of catalyst. This confirms the suitability of this methodology for the rapid access to small libraries of enantioenriched compounds.
• Organocatalyticanti-Mannich Reactions with Dihydroxyacetone and Acyclic Dihydroxyacetone Derivatives: A Facile Route to Amino Sugars
  作者：Haile Zhang、S. S. V. Ramasastry、Fujie Tanaka、Carlos F. Barbas

  DOI：10.1002/adsc.200800069

  日期：2008.4.7

  The first primary amine-containing amino acid-catalyzed anti-Mannich reactions of dihydroxyacetone and acyclic dihydroxyacetone derivatives with a variety of imines have been developed. This approach complements proline-based strategies in the preparation of amino sugars.

  已经开发出了第一羟基含伯胺的氨基酸催化的二羟基丙酮和无环二羟基丙酮衍生物与各种亚胺的抗曼尼希反应。这种方法补充了基于脯氨酸的氨基糖制备策略。