(3R,4S)-4-(4-methoxy-phenyl)-3,4-dihydroxybutan-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,4S)-4-(4-methoxy-phenyl)-3,4-dihydroxybutan-2-one
• 英文别名: (3R,4S)-3,4-dihydroxy-4-(4-methoxyphenyl)butan-2-one
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: OXDBJNMOHNJOBV-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 羟基丙酮 在 1-(4-{(2S)-2-amino-2-[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-(R)-1-methyl-ethoxycarbonyl}-butyl)-3-methyl-3H-imidazol-1-ium hexafluorophosphates 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以79%的产率得到(3R,4S)-4-(4-methoxy-phenyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  用于不对称合成羟醛反应的可持续氨基酸衍生有机催化剂

  摘要：

  鉴定了在不对称醛醇反应中导致伯氨基酸衍生的有机催化剂快速失活的不良副过程。基于这些结果设计了一种新的离子液体负载的 (S)-缬氨酸-/(S)-α,α-二苯基丝氨醇衍生催化剂 (9) 并在羟基丙酮之间的不对称合成羟醛反应中表现出更好的可回收性和醛类。此外，该催化剂似乎可用于通过不对称合成羟醛/内酯化级联反应立体选择性合成天然存在的 1(3H)-isobenzofuran-1-one 支架。

  DOI：

  10.1002/ejoc.201700166

文献信息

• Novel L-threonine-based ionic liquid supported organocatalyst for asymmetric syn-aldol reaction: activity and recyclability design
  作者：Vasiliy V. Gerasimchuk、Roman R. Romanov、Gladys H.-T. Woo、Igor A. Dmitriev、Alexander S. Kucherenko、Sergei G. Zlotin

  DOI：10.24820/ark.5550190.p010.149

  日期：——

  A novel recyclable threonine-derived ionic-liquid-supported organocatalyst of asymmetric cross-aldol reactions has been developed. In its presence, aromatic aldehydes react with hydroxyacetone, methoxyacetone and 2-butanone to afford the corresponding syn-aldol products in moderate to high yields with excellent diastereo(syn/anti up to 96:4) and enantio-selectivity (up to 95 % ee), which was retained

  已开发出一种新型可回收苏氨酸衍生的离子液体负载的不对称交叉羟醛反应有机催化剂。在它的存在下，芳香醛与羟基丙酮、甲氧基丙酮和 2-丁酮反应，以中等至高产率提供相应的合成羟醛产物，并具有优异的非对映（syn/anti 高达 96:4）和对映选择性（高达 95%） ee），它在五次回收实验中得到保留。
• Insights into Substituent Effects of Benzaldehyde Derivatives in a Heterogeneous Organocatalyzed Aldol Reaction
  作者：Graziano Di Carmine、Fabio Pesciaioli、Simeng Wang、Arianna Sinibaldi、Giuliana Giorgianni、Christopher M. A. Parlett、Armando Carlone、Carmine D'Agostino

  DOI：10.1002/cctc.202200405

  日期：2022.7.21

  heterogenous organocatalysis is undoubtedly critical to develop new and higher performing catalysts. NMR relaxation techniques provide very useful insights into adsorption effects of the aldehyde partner in an organocatalyzed aldol reaction.

  吸附：了解影响和控制多相有机催化的因素对于开发新的和更高性能的催化剂无疑是至关重要的。核磁共振弛豫技术提供了非常有用的见解，了解醛伴侣在有机催化醛醇反应中的吸附效果。
• (S)-Threonine/α,α-(S)-diphenylvalinol-derived chiral ionic liquid: an immobilized organocatalyst for asymmetric syn-aldol reactions
  作者：Natalia A. Larionova、Alexandr S. Kucherenko、Dmitry E. Siyutkin、Sergei G. Zlotin

  DOI：10.1016/j.tet.2011.01.017

  日期：2011.3

  Chiral ionic liquids containing (S)- or (R)-threonine amide and alpha,alpha-(S)-diphenylvalinol units were synthesized In the presence of the (S)-threonine-derived catalyst reactions between ketones with secondary carbon atom(s) at the alpha-position with respect to the carbonyl group and aromatic (heteroaromatic) aldehydes afforded the corresponding syn-aldols in high yields (up to 99%) and with high diastereo-(syn/anti up to 97:3) and enantioselectivity (up to 99% ee), which was maintained over three reaction cycles. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Direct <i>syn</i>- and <i>anti</i>-Aldol Reactions of Dihydroxyacetones Catalyzed by Chiral Primary Amine Catalysts
  作者：Sanzhong Luo、Hui Xu、Long Zhang、Jiuyuan Li、Jin-Pei Cheng

  DOI：10.1021/ol703023t

  日期：2008.2.1

  We present herein simple primary-tertiary diamine-Bronsted acid conjugates that catalyze both syn- and anti-adol reactions of dihydroxyacetones (DHAs) with high diastereoselectivities and enantioselectivities. This type of organocatalysts functionally mimics all four DHA aldolases, namely L-fuculose-1-phosphate aldolase, D-tagatose-1,6-diphosphate aldolase, D-fructose-1,6-diphosphate aldolase, and L-rhamnulose-1-phosphate aldolase.
• Chiral amine organocatalysts for the syn-aldol reaction involving substituted benzaldehydes and hydroxyacetone
  作者：Dhruba Sarkar、Kurt Harman、Subrata Ghosh、Allan D. Headley

  DOI：10.1016/j.tetasy.2011.05.021

  日期：2011.5

  A new series of cyclohexanediamine organocatalysts that contain the primary amine functionality has been designed, synthesized and tested as catalysts for the asymmetric aldol reaction involving hydroxyacetone and a variety of substituted benzaldehydes. High enantioselectivites and diasteroselectivites were obtained using catalyst la for these reactions. A key step in this reaction for the formation of the syn-product is the formation of a stable intramolecular hydrogen bonded Z-enamine isomer, which in addition to the steric bulk of the catalyst, serve to dictate the course of the stereochemical outcome of the reaction. (C) 2011 Elsevier Ltd. All rights reserved.