(S)-2-acetoxy-2-phenylacetic acid ethyl ester | 85879-96-5

• 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: (S)-2-acetoxy-2-phenylacetic acid ethyl ester
• 英文别名: (S)-O-acetyl ethyl mandelate；(S)-(+)-ethyl 2-acetoxy-2-phenylacetate；(R)-PhCH(OAc)C(O)OCH2Me；ethyl (2S)-2-acetyloxy-2-phenylacetate
• CAS: 85879-96-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: VTVRQPAFUYRQQH-NSHDSACASA-N

物化性质

• 沸点：
  304.6±22.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-2-acetoxy-2-phenylacetic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 氯苯 为溶剂， 反应 22.0h， 生成 (S)-[(4S)-4-methyl-4,5-dihydrooxazol-2-yl](phenyl)methanol
  参考文献：
  名称：

  Convenient synthesis of a new class of chiral hydroxymethyldihydrooxazole ligands and their application in asymmetric addition of diethylzinc to aromatic aldehydes

  摘要：

  A number of chiral hydroxymethyl-substituted dihydrooxazoles were synthesized from D- or L-mandelic acid and amino alcohols. The chiral ligands thus obtained were tested as catalyst in the asymmetric addition of diethylzinc to aromatic aldehydes, and the structure-activity relationship was studied. The addition products were characterized by an enantiomeric excess of up to 91%.

  DOI：

  10.1134/s1070428006040105
• 作为产物：
  描述：

  乙酸-4-氯苯酯 、 扁桃酸乙酯 在 [Ru(CO)2(Ph₄CpOH)]2 苯甲酰甲酸甲酯 、 Pseudomonas cepacia lipase 作用下， 以 环己烷 为溶剂， 反应 72.0h， 以74%的产率得到(S)-2-acetoxy-2-phenylacetic acid ethyl ester
  参考文献：
  名称：

  α-羟基酸酯的动态动力学拆分

  摘要：

  [分子式：见正文]酶解与钌催化的底物消旋化相结合，导致了α-羟基酯的动态动力学拆分，收率和ee良好。对不同参数的研究表明，使用洋葱假单胞菌脂肪酶，钌催化剂3和乙酸4-氯苯酯作为环己烷中的酰基供体，可获得最佳结果。

  DOI：

  10.1021/ol000014+

文献信息

• Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30
  作者：Peiran Chen、Wenhong Yang

  DOI：10.1016/j.tetlet.2014.02.095

  日期：2014.4

  By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

  通过使用脂肪酶PS-30作为催化剂，已通过立体选择性酰化反应实现了一系列外消旋扁桃酸酯的动力学拆分。动力学对映体比率（E）的值达到197.5。简要讨论了取代基的作用。
• ¹H and²H nuclear magnetic resonance determination of the enantiomeric purity and absolute configuration of α-deuteriated primary carboxylic acids, alcohols, and amines
  作者：David Parker

  DOI：10.1039/p29830000083

  日期：——

  The enantiomeric composition and absolute configuration of α-deuteriated primary carboxylic acids may be accurately determined by 1H and 2H nuclear magnetic resonance analysis of the corresponding esters of (S)-methyl 2-hydroxy-2-phenylethanoate (2). Similar methods with (S)-2-acetoxy-2-phenylethanoic acid (3) and (–)-camphanoyl chloride (1) as chiral reagents have enabled the enantiomeric purity of

  α-氘代伯羧酸的对映体组成和绝对构型可以通过对（S）-2-羟基-2-苯基甲基乙酸甲酯（2）的相应酯进行1 H和2 H核磁共振分析来准确确定。用（S）-2-乙酰氧基-2-苯基乙酸（3）和（-）-樟脑酰氯（1）作为手性试剂的类似方法使得能够测定α-氘代伯醇和伯胺的对映体纯度。这些手性试剂还可用于确定手性仲酸，醇和胺的对映体组成。
• Synthetically useful variants of industrial lipases from Burkholderia cepacia and Pseudomonas fluorescens
  作者：Kazunori Yoshida、Masakazu Ono、Takahiro Yamamoto、Takashi Utsumi、Satoshi Koikeda、Tadashi Ema

  DOI：10.1039/c7ob01823a

  日期：——

  Industrial enzymes lipase PS (LPS) and lipase AK (LAK), which originate from Burkholderia cepacia and Pseudomonas fluorescens, respectively, are synthetically useful biocatalysts. To strengthen their catalytic performances, we introduced two mutations into hot spots of the active sites (residues 287 and 290). The LPS_L287F/I290A double mutant showed high catalytic activity and enantioselectivity for

  分别源自洋葱伯克霍尔德氏菌和荧光假单胞菌的工业酶脂肪酶PS（LPS）和脂肪酶AK（LAK）是合成有用的生物催化剂。为了增强其催化性能，我们在活性位点的热点（残基287和290）中引入了两个突变。LPS_L287F / I290A双突变体对不良底物表现出较高的催化活性和对映选择性，而野生型酶显示的底物活性非常低。LAK_V287F / I290A双突变体也是一种出色的生物催化剂，具有扩大的底物范围，与LPS_L287F / I290A双突变体相当。确定热力学参数以解决双重突变体的高对映选择性的起源。该ΔΔ ^ h ‡术语，而不是ΔΔ小号‡术语，为优势，这表明对映体选择性通过与周围Phe287和ALA290分子间的相互作用相关联的差分能量驱动。观察到了显着的溶剂作用，在e值与i-Pr 2 O中具有最高E值的溶剂的log  P或ε值之间呈钟形分布。这表明具有适当疏水性和极性的有机溶剂可提供具有某
• 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.
• Garner, Charles M.; Méndez, N. Quirós; Kowalczyk, James J., Journal of the American Chemical Society, 1990, vol. 112, # 13, p. 5146 - 5160
  作者：Garner, Charles M.、Méndez, N. Quirós、Kowalczyk, James J.、Fernández, Jésus M.、Emerson, Kenneth、Larsen, Raymond D.、Gladysz

  DOI：——

  日期：——