(3R,4R)-3-hydroxy-4-(p-methoxyphenylamino)-4-(p-methoxyphenyl)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)-3-hydroxy-4-(p-methoxyphenylamino)-4-(p-methoxyphenyl)butan-2-one
• 英文别名: (3R,4R)-4-(4-methoxyphenylamino)-3-hydroxy-4-(4-methoxyphenyl)butan-2-one；(3R,4R)-3-hydroxy-4-(4-methoxyanilino)-4-(4-methoxyphenyl)butan-2-one
• 化学式: C₁₈H₂₁NO₄
• 分子量: 315.369
• InChiKey: LTEUSFZJOZGDQT-MSOLQXFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 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：
  67.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甲氧苯胺 、 4-甲氧基苯甲醛 、 羟基丙酮 在 (2S,3R)-O-(n-octanoyl)-L-threonine 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 12.0h， 生成 (3R,4R)-3-hydroxy-4-(p-methoxyphenylamino)-4-(p-methoxyphenyl)butan-2-one 、 3-hydroxy-4-(4-methoxyphenyl)-4-(4-methoxyphenylamino)butan-2-one 、 (3S,4S)-3-hydroxy-4-(p-methoxyphenylamino)-4-(p-methoxyphenyl)butan-2-one
  参考文献：
  名称：

  Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone

  摘要：

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.022

文献信息

• Enantioselective synthesis of (−)-cytoxazone and (+)-epi-cytoxazone, novel cytokine modulators via Sharpless asymmetric epoxidation and l-proline catalyzed Mannich reaction
  作者：Abhimanyu S. Paraskar、Arumugam Sudalai

  DOI：10.1016/j.tet.2006.03.079

  日期：2006.6

  A short and efficient enantioselective synthesis of (−)-cytoxazone and its stereoisomer (+)-epi-cytoxazone, novel cytokine modulators, has been described with good yield and enantioselectivity. Ti-catalyzed Sharpless asymmetric epoxidation of allyl alcohol and l-proline catalyzed three-component Mannich reaction constitute the key steps in introducing stereogenicity into the molecule.

  已经描述了新型的细胞因子调节剂（-）-cytoxazone及其立体异构体（+）- epi -cytoxazone的短而有效的对映选择性合成，具有良好的收率和对映选择性。钛催化的烯丙醇的Sharpless不对称环氧化和l-脯氨酸催化的三组分曼尼希反应构成了将立体异构性引入分子的关键步骤。
• Simple and inexpensive threonine-based organocatalysts for the highly diastereo- and enantioselective direct large-scale syn-aldol and anti-Mannich reactions of α-hydroxyacetone
  作者：Chuanlong Wu、Xiangkai Fu、Shi Li

  DOI：10.1016/j.tetasy.2011.06.022

  日期：2011.5

  Simple and inexpensive threonine-based organocatalysts that promote syn-aldol reactions and three-component asymmetric anti-Mannich reactions of alpha-hydroxyacetone achieving a respectable level of enantioselectivities are reported. The syn-aldol products could be obtained with up to a 99:1 syn/anti ratio and > 99% ee while the anti-Mannich products could be obtained with up to a 96:4 anti/syn ratio and > 99% ee. Catalyst 1c can be used efficiently on a large-scale with the enantioselectivities of the syn-aldol and anti-Mannich reactions being maintained at the same level, which offers a great possibility for application in industry. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.