2-(S)-羟基-4-氧代-4-苯基丁酸 | 146912-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-(S)-羟基-4-氧代-4-苯基丁酸
• 英文名称: (S)-2-hydroxy-4-oxo-4-phenylbutanoic acid
• 英文别名: (S)-2-hydroxy-4-oxo-4-phenylbutyric acid；2-(S)-Hydroxy-4-oxo-4-phenylbutyric Acid；(2S)-2-hydroxy-4-oxo-4-phenylbutanoic acid
• CAS: 146912-63-2
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: COFAOIWBTJSSPD-VIFPVBQESA-N

物化性质

• 熔点：
  136-139°C
• 沸点：
  437.1±35.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于丙酮（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(S)-羟基-4-氧代-4-苯基丁酸 在 palladium on activated charcoal 吡啶 、 sodium azide 、 硫酸 、 氢气 、 氯化铵 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 20.0~25.0 ℃ 、101.33 kPa 条件下， 反应 8.17h， 生成 D-高苯丙氨酸乙酯盐酸盐
  参考文献：
  名称：

  A practical synthesis of ethyl (R)- and (S)-2-hydroxy-4-phenylbutanoate and d-homophenylalanine ethyl ester hydrochloride from l-malic acid

  摘要：

  With the readily available L-malic acid as starting material. both enantiomers of ethyl 2-hydroxyl-4-phenylbutanoates and D-homophenylalanine ethyl ester hydrochloride were prepared conveniently in excellent optical purity and 64. 53 and 49% overall field. respectively. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00285-3
• 作为产物：
  描述：

  在 1,4-dihydronicotinamide adenine dinucleotide 、 β-烟酰胺腺嘌呤二核苷酸 、 sodium formate 、 三羟甲基氨基甲烷 、 1,4-二巯基-2,3-丁二醇 作用下， 反应 55.0h， 以69%的产率得到2-(S)-羟基-4-氧代-4-苯基丁酸
  参考文献：
  名称：

  使用乳酸脱氢酶的手性2-羟基-4-氧代酸和取代的2-羟基丁内酯的立体选择路线

  摘要：

  乳酸脱氢酶催化的对映选择性还原2,4-二氧杂酸提供了获得S和R构型的2-羟基-4-氧杂酸的途径。随后的非对映选择性化学还原得到4-取代的2-羟基丁内酯。

  DOI：

  10.1016/s0040-4039(00)74747-2

文献信息

• Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker’s yeast: preparation of (R)-HPB ester
  作者：Nitin W. Fadnavis、Kasiraman R. Radhika

  DOI：10.1016/j.tetasy.2004.09.007

  日期：2004.11

  Ethyl 2,4-dioxo-4-phenylbutyrate obtained by condensation of acetophenone with diethyl oxalate is reduced enantio- and regiospecifically by baker’s yeast in a diisopropyl ether/water two-phase system to give (−)-ethyl (R)-2-hydroxy-4-oxo-4-phenylbutyrate with an ee = 98% in 80% isolated yield. The hydroxyester was hydrogenated over Pd–C to obtain (−)-ethyl (R)-2-hydroxy-4-phenylbutyrate (HPB ester)

  在二异丙醚/水两相系统中，通过贝克酵母对苯乙酮与草酸二乙酯缩合得到的2,4-二氧羰基-4-苯基丁酸乙酯的对映体和区域特异性还原，得到（-）-乙基（R）-2- ee = 98％的羟基4-氧代-4-苯基丁酸酯，分离出的产率为80％。羟基酯在Pd–C上氢化，得到（-）-乙基（R）-2-羟基-4-苯基丁酸酯（HPB酯），这是ACE抑制剂合成的重要中间体。还原产物与面包酵母的长时间接触产生了3-苯基3-氧代丙醇，产率为90％。
• Asymmetric synthesis of (<i>S</i>)-dihydrokavain from <scp>l</scp>-malic acid
  作者：Mustafa Eskici、Abdullah Karanfil、M. Sabih Özer、Yalçın Kabak、İnci Durucasu

  DOI：10.1080/00397911.2018.1489057

  日期：2018.9.17

  Abstract A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite

  摘要描述了使用区域选择性从已知的 (S)-2-羟基-4-苯基丁酸乙酯合成 (S)-二氢卡瓦因的实用且有效的不对称合成，而后者又可从 L-苹果酸中作为廉价的手性池材料轻松获得。以 3,3,3-三乙氧基丙炔酸锂和随后的 HgO/H2SO4 介导的内酯化为关键步骤对 1,2-环硫酸盐进行开环。其相反的对映异构体 (R)-二氢卡瓦因也使用相同的反应序列从 d-苹果酸合成，用于光学纯度测定。图形概要
• 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.
• Hydrogenation of prochiral ketones
  申请人：Solvias AG

  公开号：EP1354883B1

  公开（公告）日：2005-12-28
• METHOD FOR PRODUCING (1R, 2S)-1-AMINO-2-VINYL CYCLOPROPANE CARBOXYLIC ACID ESTER THAT HAS IMPROVED OPTICAL PURITY
  申请人：KANEKA CORPORATION

  公开号：EP2586769B1

  公开（公告）日：2019-01-16