4-hydroxy-4-[4-(trifluoromethyl)phenyl]butan-2-one

• 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: 4-hydroxy-4-[4-(trifluoromethyl)phenyl]butan-2-one
• 化学式: C₁₁H₁₁F₃O₂
• 分子量: 232.202
• InChiKey: KTDAIWSFSAWDBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4-[4-(trifluoromethyl)phenyl]butan-2-one 在 NH₂-Val-(D-Pro)-Gly-Leu-OH 、 苯甲酸 作用下， 以 乙醇 为溶剂， 反应 110.0h， 以42%的产率得到(R)-4-hydroxy-4-[4-(trifluoromethyl)phenyl]butan-2-one
  参考文献：
  名称：

  Highly enantioselective biomimetic intramolecular dehydration: kinetic resolution of β-hydroxy ketones catalyzed by β-turn tetrapeptides

  摘要：

  Racemic beta-hydroxy ketones were kinetically resoluted into the enantiopure isomers and (E)-alpha,beta-unsaturated ketones using catalytic asymmetric intramolecular dehydration for the first time. Synthetic tetrapeptides were used to imitate fatty acid dehydratases to efficiently discriminate racemic beta-hydroxy ketones, enantioselectively catalyze the intramolecular dehydration, and result in highly enantioenriched beta-hydroxy and (E)-alpha,beta-unsaturated ketones in the environmentally benign process. Mechanistically, the high discrimination of the racemic substrates and successive enantioselective dehydration are highly dependent on the cooperative catalysis of the NH2 and COOH groups of the peptide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.03.087
• 作为产物：
  描述：

  对三氟甲基苯甲醛 、 丙酮 在 1-[2-(4-氯苯基)乙基]胍 、 DL-脯氨酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以45 %的产率得到4-hydroxy-4-[4-(trifluoromethyl)phenyl]butan-2-one
  参考文献：
  名称：

  用于有机反应官能团相容性和化学选择性信息数字化的官能团评估套件

  摘要：

  日本化学会公报，印刷前。

  DOI：

  10.1246/bcsj.20230047

文献信息

• Silica gel-mediated self-aldol reactions of highly volatile aldehydes under organic solvent-free conditions without reflux condenser
  作者：Kiyoshi Tanemura

  DOI：10.1016/j.tetlet.2019.06.030

  日期：2019.7

  Silica gel-mediated self-aldol reactions were catalyzed by piperidine to give the corresponding α,β-conjugated aldehydes in good yields. The aldol reactions of 4-nitro-, 4-trifluoromethyl-, and 4-chlorobenzaldehydes with acetone afforded the corresponding aldol products. Highly volatile aldehydes and acetone could be employed even without a reflux condenser for these reactions. Silica gel could be recycled

  哌啶催化硅胶介导的自醛醇缩合反应，以高收率得到相应的α，β-共轭醛。4-硝基-，4-三氟甲基-和4-氯苯甲醛与丙酮的醛醇缩合反应得到相应的醛醇产物。即使没有回流冷凝器，也可以使用高挥发性的醛和丙酮进行这些反应。硅胶可以循环使用五次，而产物的收率却没有显着降低。
• Asymmetric bifunctional primary aminocatalysis on magnetic nanoparticles
  作者：Sanzhong Luo、Xiaoxi Zheng、Jin-Pei Cheng

  DOI：10.1039/b812958d

  日期：——

  MNP-supported chiral primary amine catalysts were developed and evaluated as asymmetric bifunctional enamine catalysts in direct aldol reaction, showing essentially unchanged activity and stereoselectivity after 11 recycles.

  开发了MNP负载的手性伯胺催化剂，并在直接的醛醇缩合反应中将其评估为不对称双官能烯胺催化剂，在11次循环后显示出基本不变的活性和立体选择性。
• A Selective Direct Aldol Reaction in Aqueous Media Catalyzed byZinc-Proline
  作者：Ruben Fernandez-Lopez、Jacob Kofoed、Miguel Machuqueiro、Tamis Darbre

  DOI：10.1002/ejoc.200500352

  日期：2005.12

  The Zn–proline complex is shown to catalyze the aldol reaction of acetone and a wide range of arenecarbaldehydes in aqueous media, accepting even deactivated arenecarbaldehydes such as methoxybenzaldehydes in good yields. Enantiomeric excesses of up to 56 % could be obtained with 5 mol-% of the catalyst at room temperature, and up to 66 %

  Zn-脯氨酸配合物可催化丙酮和多种芳烃甲醛在水性介质中的羟醛反应，甚至可以以良好的收率接受失活的芳烃甲醛，例如甲氧基苯甲醛。在室温下使用 5 mol-% 的催化剂可以获得高达 56 % 的对映体过量，高达 66 %
• The Influence of Acidity on Direct Aldol Reactions Catalyzed by Pyrrolidine/Acid Bifunctional Organocatalyst
  作者：Yungui Peng、Changyun Ji、Chengzhi Huang、Ning Wang、Yaozhong Jiang

  DOI：10.1055/s-2005-864823

  日期：——

  match of the acidity and basicity is very important to obtain good reactivity and high yield in the pyrrolidine/acid bifunctional organocatalyst system. The combination of pyrrolidine/p-nitrophenol was a high efficiency catalyst, which has been employed in the direct aldol reaction of aldehydes and ketones with yields up to 99%.

  酸碱度的匹配对于在吡咯烷/酸双功能有机催化剂体系中获得良好的反应性和高产率非常重要。吡咯烷/对硝基苯酚的组合是一种高效催化剂，已用于醛和酮的直接羟醛反应，收率高达99%。
• Application of Deep Eutectic Solvents in Promiscuous Lipase-Catalysed Aldol Reactions
  作者：Daniel González-Martínez、Vicente Gotor、Vicente Gotor-Fernández

  DOI：10.1002/ejoc.201501553

  日期：2016.3

  The application of deep eutectic solvents has been demonstrated for the first time in promiscuous lipase-catalysed aldol reactions. The model reaction between 4-nitrobenzaldehyde and acetone was examined in depth, with excellent compatibility being found between porcine pancreas lipase and choline chloride/glycerol mixtures for the formation of the aldol product in high yields. The system was compatible

  首次在混合脂肪酶催化的羟醛反应中证明了深共熔溶剂的应用。深入研究了 4-硝基苯甲醛和丙酮之间的模型反应，发现猪胰腺脂肪酶和氯化胆碱/甘油混合物之间具有极好的相容性，可高产率地形成醛醇产物。该系统与一系列芳香醛和酮兼容，包括丙酮、环戊酮和环己酮。在某些情况下，发现相应的 α,β-不饱和羰基化合物是次要产物。对照实验表明，一旦形成羟醛产物，酶制剂也负责附带的脱水反应。