(-)-(S)-1-(2-Pyridyl)ethyl acetate | 27854-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (-)-(S)-1-(2-Pyridyl)ethyl acetate
• 英文别名: (S)-1(pyridin-2-yl)ethyl acetate；(S)-1-(2-pyridyl)ethyl acetate；[(1S)-1-pyridin-2-ylethyl] acetate
• CAS: 27854-83-7
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: QLLUWUDOCNQQAH-ZETCQYMHSA-N

物化性质

• 沸点：
  218.3±15.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(S)-1-(2-Pyridyl)ethyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (S)-1-(吡啶-2-基)乙醇
  参考文献：
  名称：

  Preparation of optically pure pyridyl-1-ethanols

  摘要：

  Using a highly enantioselective lipase from Pseudomonas sp. (SAM II) all enantiomers of the isomeric pyridyl-1-ethanols (R)- and (S)- 1 - 3 were prepared in optically pure form both by enzymatic hydrolysis and esterification.

  DOI：

  10.1016/s0957-4166(00)82175-8
• 作为产物：
  描述：

  (S)-(6-bromopyridin-2-yl)ethanol 在 吡啶 、 三苯基膦 、 nickel dichloride 、 锌 作用下， 反应 23.25h， 生成 (-)-(S)-1-(2-Pyridyl)ethyl acetate
  参考文献：
  名称：

  Bolm, Carsten; Ewald, Martina; Felder, Marcel, Chemische Berichte, 1992, vol. 125, # 5, p. 1169 - 1190

  摘要：

  DOI：

文献信息

• The importance of ester and alkoxy type functionalities for the chemo- and enantio-recognition of substrates by hydrolysis with Candida rugosa lipase
  作者：Francesca Bellezza、Antonio Cipiciani、Gabriele Cruciani、Francesco Fringuelli

  DOI：10.1039/b005512n

  日期：——

  Racemic esters of 1-phenyl- and 1-(pyridyl)ethyl acetates 1a–c (R = Me, Ph) were subjected to hydrolysis in water in the presence of Candida rugosa lipase (CRL). 1-Pyridylethyl acetates (1, R = Me) are hydrolyzed by crude CRL (C-CRL) and isopropanol (isopropyl alcohol) treated CRL (PT-CRL) at very low rates, and the enantiorecognition was disappointing. By using 1-pyridylethyl benzoates (1, R = Ph) the results differed greatly: hydrolysis occurred much faster, and the enantiorecognition was good for 3- and 4-pyridyl derivatives and excellent for 2-pyridyl derivative. Analogous results were obtained by submitting the 1-phenylethanol esters 4 to enzymatic hydrolysis under the same experimental conditions. The hydrolysis of methyl o-acetoxybenzoates 7 (R = Me) gave quantitatively the deacetylated methyl o-hydroxybenzoates 9 (R = Me) by using either C-CRL or PT-CRL. A complete reversed selectivity is observed in the hydrolysis of phenyl o-acetoxybenzoates 7 (R = Ph) catalyzed by PT-CRL. Molecular modeling studies, aimed at probing the substrate specificity and the enantioselectivity of enzyme in terms of its three-dimensional structure is reported.

  1-苯基和1-(吡啶基)乙酸酯的消旋酯1a–c（R=甲基，苯基）在皱褶假丝酵母脂酶（CRL）存在下水解。1-吡啶基乙酸酯（1，R=甲基）在粗制CRL（C-CRL）和异丙醇（异丙基酒精）处理过的CRL（PT-CRL）作用下的水解速率非常低，且对映体识别令人失望。使用1-吡啶基苯甲酸酯（1，R=苯基）时结果大不相同：水解速率快得多，且对映体识别对于3-和4-吡啶衍生物良好，对于2-吡啶衍生物非常优异。在相同实验条件下进行1-苯乙醇酯4的酶促水解也得到了类似的结果。甲基邻乙酰氧基苯甲酸酯7（R=甲基）的水解在C-CRL或PT-CRL的作用下完全转化为脱乙酰化的甲基邻羟基苯甲酸酯9（R=甲基）。在PT-CRL催化的苯基邻乙酰氧基苯甲酸酯7（R=苯基）的水解中，观察到了完全相反的选择性。报道了旨在探究酶的三维结构对底物特异性和对映选择性的分子建模研究。
• Application of Ruthenium Complexes of Triazole-Containing Tridentate Ligands to Asymmetric Transfer Hydrogenation of Ketones
  作者：Tarn C. Johnson、William G. Totty、Martin Wills

  DOI：10.1021/ol302354z

  日期：2012.10.19

  The synthesis of a series of tridentate ligands based on a homochiral 1,2-diamine structure attached to a triazole group and their subsequent applications to the asymmetric transfer hydrogenation of ketones are described. In the best cases, alcohols of up to 93% ee were obtained. Although base is not required, the use of Ru3(CO)12 as metal source is essential, indicating a unique mechanism for the

  描述了基于与三唑基连接的同手性1,2-二胺结构的一系列三齿配体的合成及其在酮的不对称转移氢化中的后续应用。在最佳情况下，获得的酒精含量高达ee的93％。尽管不需要碱，但是必须使用Ru 3（CO）12作为金属源，这表明形成活性催化剂的独特机理。
• Spiroborate esters in the borane-mediated asymmetric synthesis of pyridyl and related heterocyclic alcohols
  作者：Viatcheslav Stepanenko、Melvin De Jesús、Wildeliz Correa、Irisbel Guzmán、Cindybeth Vázquez、Lymaris Ortiz、Margarita Ortiz-Marciales

  DOI：10.1016/j.tetasy.2007.10.044

  日期：2007.11

  The effectiveness of several spiroborate ester catalysts was investigated in the asymmetric borane reduction of 2-, 3-, and 4-acetylpyriclines under different reaction conditions. Highly enantiomerically enriched 1-(2-, 3-, and 4-pyridyl)ethanols and 1-(heterocyclic)ethanols were obtained using 1-10% catalytic loads of the spiroborate 5 derived from diphenylprolinol and ethylene glycol. (c) 2007 Elsevier Ltd. All rights reserved.
• Reduction of β-Keto Esters with a Reductase: Construction of Plural Stereocenters Remote from the Reaction Center
  作者：Yasushi Kawai、Kouichi Hida、Atsuyoshi Ohno

  DOI：10.1006/bioo.1998.1106

  日期：1999.2

  The reduction of sec-alkyl 2-methyl-3-oxobutyrate with a keto ester reductase from bakers' yeast (YKER-I) is accompanied by simultaneous dynamic and static resolution of chiral centers affording the corresponding (2R,3S,1'R)-hydroxy esters preferentially Thus, the enzyme discriminates three chiral centers simultaneously in high stereoselectivity producing useful chiral building blocks. To study the effect of the alcohol moiety which is located at a remote position from the reaction center, upon the interaction between the enzyme and a substrate, steady-state kinetic parameters, K-m and k(cat), of YKER-I for each (1'R)- and (1'S)-substrate have been determined. The results reveal that the stereochemistry at the alcohol moiety affects K-m rather than k(cat). (C) 1999 Academic Press.