(1R)-1-(3-吡啶基)乙酸乙酯 | 27854-86-0

• 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
• 中文名称: (1R)-1-(3-吡啶基)乙酸乙酯
• 英文名称: (1R)-1-(3-pyridyl)ethyl acetate
• 英文别名: (R)-1-(3-Pyridyl)ethyl acetate；[(1R)-1-pyridin-3-ylethyl] acetate
• CAS: 27854-86-0
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: OJKZGAXVEUJEIZ-SSDOTTSWSA-N

物化性质

• 沸点：
  240.2±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)：
  0.9
• 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：

  (1R)-1-(3-吡啶基)乙酸乙酯 在 sodium tetrahydroborate 、 potassium carbonate 、 三甲基乙酸 作用下， 以 甲醇 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 (R,Z)-benzyl 3-ethylidene-4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate
  参考文献：
  名称：

  An enantioselective synthesis of the Strychnos alkaloid (−)-tubifoline

  摘要：

  An enantioselective synthesis of the Strychnos alkaloid (-)-tubifoline, involving the kinetic resolution of racemic 1-(3-pyridyl)ethanol, the orthoester Claisen rearrangement of the enantiopure allylic alcohol 5, Smith indolization of the resulting 4-piperidineacetate 6, photocyclization of chloroacetamide 9, and final transannular cyclization, is reported. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00359-x
• 作为产物：
  描述：

  3-(1-羟乙基)吡啶 以 异丙醚 为溶剂， 反应 0.67h， 生成 (1R)-1-(3-吡啶基)乙酸乙酯
  参考文献：
  名称：

  Remarkably improved stability and enhanced activity of a Burkholderia cepacia lipase by coating with a triazolium alkyl-PEG sulfate ionic liquid

  摘要：

  合成了三种三唑基十辛基PEG10硫酸盐离子液体，并研究了它们对Burkholderia cepacia脂肪酶的活化作用。

  DOI：

  10.1039/c7gc02319g

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。
• Increased Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification by Using an Imidazolium PEG–Alkyl Sulfate Ionic Liquid
  作者：Toshiyuki Itoh、Yuichi Matsushita、Yoshikazu Abe、Shi-hui Han、Shohei Wada、Shuichi Hayase、Motoi Kawatsura、Shigeomi Takai、Minoru Morimoto、Yoshihiko Hirose

  DOI：10.1002/chem.200601043

  日期：2006.12.13

  types of imidazolium salt ionic liquids were prepared derived from poly(oxyethylene)alkyl sulfate and used as an additive or coating material for lipase-catalyzed transesterification in an organic solvent. A remarkably increased enantioselectivity was obtained when the salt was added at 3-10 mol % versus substrate in the Burkholderia cepacia lipase (lipase PS-C)-catalyzed transesterification of 1-phenylethanol

  从聚（氧乙烯）烷基硫酸酯制备了几种类型的咪唑鎓盐离子液体，并用作在有机溶剂中脂肪酶催化的酯交换反应的添加剂或涂料。通过在二异丙醚或己烷溶剂体系中使用乙酸乙烯酯，在伯克霍尔德菌洋葱脂肪酶（脂肪酶PS-C）催化的1-苯基乙醇酯交换反应中，以相对于底物3-10 mol％的量添加盐时，可获得显着提高的对映选择性。尤其是，在iPr（2）O溶剂系统中，用脂肪酶PS进行离子液体涂覆可实现显着的加速，同时保持出色的对映选择性。对于某些具有出色对映选择性的底物，它达到了约500至1000倍的加速度。对于IL 1包被的假丝酵母念珠菌脂肪酶也观察到类似的加速。离子液体包被的脂肪酶PS的MALDI-TOF质谱实验表明，离子液体与脂肪酶蛋白结合。
• Total syntheses of the Strychnos indole alkaloids(−)-tubifoline, (−)-tubifolidine, and (−)-19,20-dihydroakuammicine
  作者：Mercedes Amat、M.-Dolors Coll、Joan Bosch、Enric Espinosa、Elies Molins

  DOI：10.1016/s0957-4166(97)00071-2

  日期：1997.3

  Two different stragies for the synthesis of pentacyclic Strychnos alkaloids in enantiomerically pure form are explored. Both of them involve the use of enantiopure 2-(4-piperidylmethyl)indoles prepared by kinetic resolution of 1-(3-pyridyl)ethanol, followed by partial reduction of the pyridine ring to the tetrahydropyridine level, Claisen rearrangement of the resulting allylic alcohol, and finally

  为五环的合成两种不同stragies马钱子生物碱在对映体纯的形式进行了探索。它们都涉及使用对映体纯的2-（4-哌啶基甲基）吲哚，其是通过动力学拆分1-（3-吡啶基）乙醇而制备的，然后将吡啶环部分还原成四氢吡啶水平，将所得的烯丙醇进行克莱森重排。 ，最后是史密斯的化身。而2-（4-哌啶基甲基）吲哚6不能转换到的四环ABDE子马钱子碱，氯乙酰胺的photocyclization 14，从（哌啶基甲基）吲哚衍生的13，令人满意地得到stemmadenine型四环15，然后将其转化为生物碱（-）-tubifoline，（-）-tubifolidine和（-）-19,20-dihydroakuammicine。
• Enhanced activity and modified substrate-favoritism of Burkholderia cepacia lipase by the treatment with a pyridinium alkyl-PEG sulfate ionic liquid
  作者：Shiho Kadotani、Toshiki Nokami、Toshiyuki Itoh

  DOI：10.1016/j.tet.2018.12.028

  日期：2019.1

  Three types of pyridinium salts, i.e., 1-ethylpyridin-1-ium cetyl-PEG(10) sulfate (PYET), 1-butylpyridin-1-ium cetyl-PEG(10) sulfate (PYBU), and 1-(3-methoxypropyl)pyridin-1-ium cetyl-PEG(10) sulfate (PYMP), have been prepared and evaluated for their activation property of Burkholderia cepacia lipase by comparison to the control IL-coated enzymes, 1-butyl-2,3-dimethylimidazolium cetyl-PEG(10) sulfate-coated lipase PS (1L1-PS). Among the tested pyridinium salt-coated lipases, the PYET-coated lipase PS (PYET-PS) exhibited the best results; the transesterification of 1-(pyridin-2-yl)ethanol, 1-(pyridin-3-yl)ethanol, 1-(pyridin-4-yl)ethanol, or 4-phenylbut-3-en-2-ol proceeded faster than those of the IL1-PS-catalyzed reaction while maintaining an excellent enantioselectivity (E > 200). This improved efficiency was found to be dependent on the increased K-cat value. (C) 2018 Elsevier Ltd. All rights reserved.
• Preparation of optically pure pyridyl-1-ethanols
  作者：Robert Seemayer、Manfred P. Schneider

  DOI：10.1016/s0957-4166(00)82175-8

  日期：1992.7

  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.