(R)-2-acetoxy-2-phenylacetic acid ethyl ester | 74364-75-3

• 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: (R)-2-acetoxy-2-phenylacetic acid ethyl ester
• 英文别名: (R)-(+)-ethyl 2-acetoxy-2-phenylacetate；(R)-acetoxy-phenyl-acetic acid ethyl ester；(R)-Acetoxy-phenyl-essigsaeure-aethylester；ethyl (2R)-2-acetyloxy-2-phenylacetate
• CAS: 74364-75-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: VTVRQPAFUYRQQH-LLVKDONJSA-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：

  (R)-2-acetoxy-2-phenylacetic acid ethyl ester 在 盐酸 作用下， 反应 4.0h， 以985 mg的产率得到D-扁桃酸
  参考文献：
  名称：

  通过相应乙酸盐的微生物不对称水解合成旋光炔醇和α-羟基酯

  摘要：

  枯草芽孢杆菌变种对消旋炔醇和α-羟基酯的乙酸酯的不对称水解。尼日尔提供了7–90％的光学纯度的旋光乙酸酯和醇。通过该微生物方法制备光学纯的扁桃酸的两种对映体。

  DOI：

  10.1016/0040-4020(80)85030-7
• 作为产物：
  描述：

  扁桃酸乙酯 在 吡啶 作用下， 反应 77.0h， 生成 (R)-2-acetoxy-2-phenylacetic acid ethyl ester
  参考文献：
  名称：

  通过相应乙酸盐的微生物不对称水解合成旋光炔醇和α-羟基酯

  摘要：

  枯草芽孢杆菌变种对消旋炔醇和α-羟基酯的乙酸酯的不对称水解。尼日尔提供了7–90％的光学纯度的旋光乙酸酯和醇。通过该微生物方法制备光学纯的扁桃酸的两种对映体。

  DOI：

  10.1016/0040-4020(80)85030-7

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。
• Tritiated Chiral Alkanes as Substrates for Soluble Methane Monooxygenase from <i>Methylococcus capsulatus</i> (Bath):  Probes for the Mechanism of Hydroxylation
  作者：Ann M. Valentine、Barrie Wilkinson、Katherine E. Liu、Sonja Komar-Panicucci、Nigel D. Priestley、Philip G. Williams、Hiromi Morimoto、Heinz G. Floss、Stephen J. Lippard

  DOI：10.1021/ja963971g

  日期：1997.2.1

  tritiated chiral alkanes (S)-[1-2H1,1-3H]ethane, (R)-[1-2H1,1-3H]ethane, (S)-[1-2H1,1-3H]butane, (R)-[1-2H1,1-3H]butane, (S)-[2-3H]butane, (R)-[2-3H]butane, and racemic [2-3H]butane were oxidized by soluble methane monooxygenase (sMMO) from Methylococcus capsulatus (Bath), and the absolute stereochemistry of the resulting product alcohols was determined in order to probe the mechanism of substrate hydroxylation

  氚化手性烷烃 (S)-[1-2H1,1-3H] 乙烷, (R)-[1-2H1,1-3H] 乙烷, (S)-[1-2H1,1-3H] 丁烷, ( R)-[1-2H1,1-3H]丁烷、(S)-[2-3H]丁烷、(R)-[2-3H]丁烷和外消旋[2-3H]丁烷被可溶性甲烷单加氧酶氧化(sMMO) 来自荚膜甲基球菌 (Bath)，并测定所得产物醇的绝对立体化学，以探测底物羟基化的机制。当使用纯化的羟化酶、偶联蛋白和还原酶成分时，产物醇在标记碳上对乙烷底物显示出 72% 的立体化学保留，对在初级碳上标记的丁烷显示出 77% 的保留。产生这些产物分布的推定烷基的寿命为 100 fs，该值太短而不能对应于离散的中间体。乙烷和丁烷的分子内 kH/kD 比分别为 3.4 和 2.2。当用纯化的羟化酶进行羟基化但只有部分...
• Convenient synthesis of a new class of chiral hydroxymethyldihydrooxazole ligands and their application in asymmetric addition of diethylzinc to aromatic aldehydes
  作者：Zhi-ting Li、Xin-sheng Li、Liang-chao Li、Dong-cheng Xu

  DOI：10.1134/s1070428006040105

  日期：2006.4

  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%.
• Central and peripheral glucocorticoid receptor function in abdominal obesity
  作者：T. Ljung、M. Ottosson、A. C. Ahlberg、S. Edén、B. Odén、S. Okret、M. Brönnegård、P. Stierna、P. Björntorp

  DOI：10.1007/bf03343995

  日期：2002.3

  Abdominal obesity seems to be associated with a moderately deranged feedback regulation of the hypothalamic-pituitary-ad renal (HPA) axis where central glucocorticoid receptors (GR) are involved. Therefore, functions of central and peripheral GR were compared in this study. Furthermore, since trinucleotide repeats in early exons of steroid hormone receptor genes influence transcription, and therefore may influence receptor density, this was also studied. Ten middle-aged men, 5 with abdominal obesity and 5 controls, were studied. The suppression of dexamethasone (dex) on serum cortisol was used in dose-response tests to assess the function of central GR. Abdominal adipose tissue biopsies were incubated and exposed to cortisol in different concentrations, and the function of the peripheral GR assayed as induction of lipoprotein lipase (LPL) activity. Aberrant expansion of exonic trinucleotide repeats in the first coding exon of the GR gene was studied by sequencing of genomic DNA. Results showed that men with abdominal obesity showed less inhibition of serum cortisol by dex, particularly at lower concentrations, while in the controls cortisol secretion was inhibited in an apparent dose-response manner. LPL activity in adipose tissue was lower in abdominal obese men than in controls. However, the sensitivity to cortisol was not different between the groups. There was no evidence for expansion of trinucleotide repeats. These results suggest that the central GR and the peripheral GR in adipose tissue exhibit functional differences in abdominal obesity.
• N-Acylpyridinium Trifluoromethanesulfonates and Tetrafluoroborates: Shuttle Reagents for the Acylation of Enantiopure Secondary Alcohols
  作者：Rüdiger Wagner

  DOI：10.1055/s-1998-2074

  日期：1998.6