(3R,4S)-4-(4-fluorophenyl)-3,4-dihydroxybutan-2-one | 1269058-57-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,4S)-4-(4-fluorophenyl)-3,4-dihydroxybutan-2-one
• CAS: 1269058-57-2
• 化学式: C₁₀H₁₁FO₃
• 分子量: 198.194
• InChiKey: PJVRIYDABLEHCT-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  对氟苯甲醛 、 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， 生成 (3R,4S)-4-(4-fluorophenyl)-3,4-dihydroxybutan-2-one 、 (3R,4S)-4-(4-fluorophenyl)-3,4-dihydroxybutan-2-one
  参考文献：
  名称：

  (S)-Threonine/α,α-(S)-diphenylvalinol-derived chiral ionic liquid: an immobilized organocatalyst for asymmetric syn-aldol reactions

  摘要：

  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.

  DOI：

  10.1016/j.tet.2011.01.017

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。
• Pepsin-catalyzed direct asymmetric aldol reactions for the synthesis of vicinal diol compounds
  作者：Ling-Yu Li、Da-Cheng Yang、Zhi Guan、Yan-Hong He

  DOI：10.1016/j.tet.2015.01.061

  日期：2015.3

  The catalytic promiscuity of pepsin from porcine gastric mucous was observed in catalysis of the direct asymmetric aldol reactions of aromatic aldehydes with acetones, which were substituted by hydroxy-, dihydroxy-, methoxy- and benzyloxy- for the synthesis of diol compounds in acetonitrile. This biocatalysis was also applicable to the aldol reactions of cyclic or hetereocyclic ketones with aromatic

  在催化芳香族醛与丙酮直接不对称醛醇缩合反应的催化过程中，观察到了胃蛋白酶对胃蛋白酶的混杂作用，丙酮醛被羟基，二羟基，甲氧基和苄氧基所取代，从而在乙腈中合成二醇化合物。该生物催化也适用于环状或杂环酮与芳族醛的醛醇缩合反应。获得了高达87％的产率，高达> 99/1 dr的非对映选择性和高达75％ee的对映选择性。
• Simple and practical direct asymmetric aldol reaction of hydroxyacetone catalyzed by 9-amino Cinchona alkaloid tartrates
  作者：Paweł Czarnecki、Agnieszka Plutecka、Jacek Gawroński、Karol Kacprzak

  DOI：10.1039/c1gc15064b

  日期：——

  procedure for the direct aldol reaction of unprotected acetol and activated aromatic aldehydes catalyzed by 9-amino-9-epi-Cinchona ditartrates is presented. The protocol presented avoids the use of problematic solvents and toxic reagents as well as chromatographic purification of the products – instead a simple extraction has been applied for the isolation of pure aldols from the reaction mixture. This

  一种新的有机催化方法，用于未保护基的直接羟醛反应 丙酮醇 和活化的芳烃 醛类 由...催化 9-氨基-9-外延-金鸡纳介绍了酒石酸氢盐。提出的协议避免了使用有问题的溶剂 和有毒试剂以及色谱 纯化 产品–而不是简单的 萃取已用于从反应混合物中分离纯羟醛。这个催化该系统专门为线性羟醛提供定量的收率，并具有高达90％ee的良好的顺-非对映选择性和对映选择性。通过单一且可靠的方法，可以轻松完成对映体过量的顺式对映体的进一步纯化，最高可达到ee的99％结晶。指某东西的用途辛可宁 或者 奎宁-衍生的 催化剂允许获得其绝对构型由决定的顺式醇的两个对映体的对映体X射线衍射。使用廉价和可再生化学品的操作方便且可扩展的有机催化程序–两者丙酮醇 和 催化剂，提供了一种可持续的绿色方式来合成许多α-酮-合成-二醇。
• 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。
• 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.