4-(4-methoxy-phenyl)-3,4-dihydroxybutan-2-one | 1007872-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxy-phenyl)-3,4-dihydroxybutan-2-one
• 英文别名: 3,4-Dihydroxy-4-(4-methoxyphenyl)butan-2-one；3,4-dihydroxy-4-(4-methoxyphenyl)butan-2-one
• CAS: 1007872-97-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: OXDBJNMOHNJOBV-UHFFFAOYSA-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 sodium hydroxide 作用下， 以 水 为溶剂， 反应 9.0h， 以46%的产率得到4-(4-methoxy-phenyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  通过在水中原位生成硼“酸酯”配合物烯醇化物而产生的醛醇催化反应和缩合反应。

  摘要：

  DOI：

  10.1002/anie.200704293

文献信息

• Towards Sustainable Amino Acid Derived Organocatalysts for Asymmetric <i>syn</i> -Aldol Reactions
  作者：Vasiliy V. Gerasimchuk、Alexandr S. Kucherenko、Artem N. Fakhrutdinov、Michael G. Medvedev、Yulia V. Nelyubina、Sergei G. Zlotin

  DOI：10.1002/ejoc.201700166

  日期：2017.5.3

  side-processes responsible for the fast deactivation of primary amino acid derived organocatalysts in asymmetric aldol reactions are identified. A new ionic-liquid-supported (S)-valine-/(S)-α,α-diphenylserinol-derived catalyst (9) is designed on the basis of these results and exhibits much better recyclability in asymmetric syn-aldol reactions between hydroxyacetone and aldehydes. Furthermore, this catalyst

  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。
• 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。
• 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.
• 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.