ethyl 2-hydroxy-4-oxo-4-phenylbutanoate | 91497-49-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-hydroxy-4-oxo-4-phenylbutanoate
• CAS: 91497-49-3
• 化学式: C₁₂H₁₄O₄
• mdl: MFCD00043878
• 分子量: 222.241
• InChiKey: HEWAMPODKFTBJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-hydroxy-4-oxo-4-phenylbutanoate 在 咪唑 、 硼氘化钠 、 氘代甲醇-d 、 乙基苯 、 palladium on activated carbon 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.45h， 生成 syn-ethyl 2-((tert-butyldimethylsilyl)oxy)-4-phenylbutanoate-4-d
  参考文献：
  名称：

  苯甲醇在Pd / C上的立体定向氢解。

  摘要：

  叔苄醇在钯碳（Pd / C）上的氢解反应通常会发生构型转化。但是，关于伯和仲苄醇的氢解机理知之甚少。文献先例表明这些底物可能与催化剂发生不同的相互作用。为了研究该机理，我们合成了一对氘代非对映异构体，其手性中心位于苄基位置。氢解产物的化学衍生化表明，反应随着这些底物的构型转化而进行。

  DOI：

  10.1021/acs.joc.0c00827
• 作为产物：
  描述：

  ethyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate 在 水 、 铁粉 、 氯化铵 作用下， 以 乙醇 为溶剂， 以59 %的产率得到ethyl 2-hydroxy-4-oxo-4-phenylbutanoate
  参考文献：
  名称：

  可见光介导的三组分合成异恶唑啉和异恶唑的策略

  摘要：

  异恶唑啉和异恶唑通常用作许多治疗剂和天然产物的核心结构。然而，在室温下合成这些特殊基序的无金属和无催化策略仍然是一项具有挑战性的任务。在此，我们报告了一种三组分策略，通过在可见光照射下原位形成的硝基化合物和烯烃/炔烃的[3 + 2]环加成提供不同的异恶唑啉和异恶唑。

  DOI：

  10.1021/acs.orglett.4c00671

文献信息

• Bismuth Triflate Catalyzed Mukaiyama Aldol Reaction in an Ionic Liquid
  作者：Thierry Ollevier、Valerie Desyroy、Blandine Debailleul、Sophie Vaur

  DOI：10.1002/ejoc.200500621

  日期：2005.12

  We have developed an efficient, bismuth triflate catalyzed Mukaiyama aldol reaction. The reaction proceeds rapidly and affords the corresponding β-hydroxy carbonyl compound in moderate to very good yields (up to 92 %). (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  我们开发了一种高效的三氟甲磺酸铋催化Mukaiyama aldol反应。反应迅速进行并以中等至非常高的产率（高达92％）得到相应的β-羟基羰基化合物。（©Wiley-VCH Verlag GmbH＆Co.KGaA，69451 Weinheim，Germany，2005）
• Base- and metal-free decarboxylative aldol reaction of β-ketoacids with glyoxylate hydrates and glyoxal monohydrates in water
  作者：Nan Ren、Jing Nie、Jun-An Ma

  DOI：10.1039/c6gc02705a

  日期：——

  An environmental benign decarboxylative aldol reaction of [small beta]-ketoacids with glyoxylate and glyoxal monohydrates in water is reported. The reaction proceeds smoothly without any base and metal catalysts, affording the correspoding...

  报道了水中小β-酮酸与乙醛酸酯和乙二醛一水合物的环境良性脱羧醛醇缩合反应。反应平稳进行，无需任何碱和金属催化剂，得到了相应的...
• Cu(0) nanoparticle catalyzed efficient reductive cleavage of isoxazoline, carbonyl azide and domino cyclization in water medium
  作者：Krishnanka S. Gayen、Tista Sengupta、Yasmin Saima、Adita Das、Dilip K. Maiti、Atanu Mitra

  DOI：10.1039/c2gc35252d

  日期：——

  Small Cu(0)-nanoparticles (NPs) are fabricated utilizing CuSO4·5H2O, surfactant (SDS) and ascorbic acid in aqueous medium. Its outstanding catalytic activity under low catalyst loading is developed toward reductive cleavage of isoxazoline, carbonyl azide and domino cyclization to furnish valuable 2-hydroxy-4-keto esters, primary amides and a new class of heterocycle, 4-hydroxy-2-pyrroline-5-one.

  利用 CuSO4-5H2O、表面活性剂（SDS）和抗坏血酸在水介质中制造出了小型 Cu(0)- 纳米粒子（NPs）。在低催化剂负载条件下，该催化剂具有出色的催化活性，可还原裂解异噁唑啉、叠氮羰基和多米诺环化反应，生成有价值的 2-hydroxy-4-keto 酯、伯酰胺和一类新型杂环 4-hydroxy-2-pyrroline-5-one 。
• Probing the mechanism of direct Mannich-type α-methylenation of ketoesters via electrospray ionization mass spectrometry
  作者：Cíntia D. F. Milagre、Humberto M. S. Milagre、Leonardo S. Santos、Marcelo L. A. Lopes、Paulo J. S. Moran、Marcos N. Eberlin、J. Augusto R. Rodrigues

  DOI：10.1002/jms.1173

  日期：2007.10

  Reactions promoting direct Mannich-type alpha-methylenation of alpha, beta and gamma-ketoesters have been monitored via electrospray ionization mass and tandem mass spectrometric experiments. Key intermediates of the catalytical cycle of this synthetically useful reaction have been intercepted and characterized. The mechanistic information provided by electrospray ionization mass spectrometry/mass

  通过电喷雾电离质谱和串联质谱实验已监测了促进α，β和γ-酮酸酯直接曼尼希型α-甲基化的反应。该合成有用的反应的催化循环的关键中间体已被拦截和表征。电喷雾电离质谱/质谱（ESI-MS / MS）提供的机理信息指导了反应条件的优化，从而可以高产率（80-95％）和高纯度制备α-亚甲基酮酸酯进一步操作。
• Lipase activity of Lecitase® Ultra: characterization and applications in enantioselective reactions
  作者：Mithilesh Kumar Mishra、Thenkrishnan Kumaraguru、Gurrala Sheelu、Nitin W. Fadnavis

  DOI：10.1016/j.tetasy.2009.11.012

  日期：2009.12

  The general properties of Lecitase (R) Ultra, a phospholipase manufactured and marketed by Novozymes, Denmark, have been studied after purification by ultrafiltration. The enzyme has a molecular mass of 35 KD, pH-optimum of 8.5, and appears to possess a single active site which exhibits both the lipase and phospholipase activities that increase in the presence of Ca2+ and Mg2+ ions. The enzyme is inhibited by heavy metal ions and surfactants, and does not accept p-nitrophenyl acetate and glycerol triacetate. Substrates, such as glycerol tributyrate and p-nitrophenyl palmitate, esters of N-acetyl-alpha-amino acids and alpha-hydroxy acids are readily accepted. Amino acids with aliphatic residues, such as alanine, isoleucine, and methionine, are hydrolyzed with high enantioselectivity for the L-enantiomer (E > 100), but amino acids with aromatic residues such as phenylalanine and phenylglycine, and esters of alpha-hydroxy acids are hydrolyzed with low enantioselectivity (E = 1-5). Immobilization of the enzyme in a gelatin matrix (gelozyme) leads to a marginal improvement in the enantioselectivity for these substrates. However, a dramatic improvement in enantioselectivity is observed for ethyl 2-hydroxy-4-oxo-4-phenylbutyrate (E value increases from 4.5 to 19.5 with S-selectivity). Similarly, glycidate esters, such as ethyl trans-(+/-)-3-phenyl glycidate and methyl trans-(+/-)-3-(4-methoxyphenyl) glycidate, are selectively hydrolyzed with a remarkable selectivity towards the (2S,3R)-enantiomer providing unreacted (2R,3S)-glycidate esters (ee >99%, conversion 52-55%) by the immobilized enzyme. (C) 2009 Elsevier Ltd. All rights reserved.