(S)-2-(4-Chloro-phenoxy)-propionic acid butyl ester | 139930-23-7

• 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-(4-Chloro-phenoxy)-propionic acid butyl ester
• 英文别名: butyl (2S)-2-(4-chlorophenoxy)propanoate
• CAS: 139930-23-7
• 化学式: C₁₃H₁₇ClO₃
• 分子量: 256.729
• InChiKey: OQNVBMVZEYHHRH-JTQLQIEISA-N

物化性质

• 沸点：
  326.3±17.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-(4-Chloro-phenoxy)-propionic acid butyl ester 在 水 作用下， 以 异辛烷 为溶剂， 生成 (S)-2-(4-chlorophenoxy)propionic acid 、 正丁醇
  参考文献：
  名称：

  Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems

  摘要：

  DOI：

  10.1021/ja00243a040
• 作为产物：
  描述：

  2-(4-氯苯氧基)丙酸 、 正丁醇 以 正庚烷 为溶剂， 反应 1.5h， 生成 (S)-2-(4-Chloro-phenoxy)-propionic acid butyl ester
  参考文献：
  名称：

  Candida rugosa lipase: Enantioselectivity enhancements in organic solvents

  摘要：

  Chiral resolutions of carboxylic acids (1-3) and alcohol (4) were carried out through esterification or transesterification in organic solvents using cross-linked enzyme crystals (CLEC(R)) of Candida rugosa lipase (CRL). Comparison of these results with those of elude CRL reveal significant differences. As was seen in resolution through hydrolysis,(1) a marked improvement in enantioselectivity is realized with the CLEC. Additionally, the stability afforded the enzyme in CLEC form leads to a higher activity in organic solvent. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0040-4039(96)01430-x

文献信息

• Drastic enhancement of the enantioselectivity of lipase-catalysed esterification in organic solvents by the addition of metal ions
  作者：Takashi Okamoto、Shinichi Ueji

  DOI：10.1039/a902255d

  日期：——

  By the addition of metal ion-containing water, a marked enhancement of the enantioselectivity for the lipase-catalysed esterification of 2-(4-substituted-phenoxy)propionic acids in Pri2O was observed, the mechanism of which will be discussed briefly on the basis of the initial rate obtained for each enantiomer of the substrate.

  通过添加含金属离子的水，观察到在Pri2O中，2-(4-取代苯氧)丙酸的脂肪酶催化酯化反应的对映选择性显著增强，机制将基于每个底物对映体的初始速率进行简要讨论。
• Effects of Substituent and Temperature on Enantioselectivity for Lipase-Catalyzed Esterification of 2-(4-Substituted Phenoxy) Propionic Acids in Organic Solvents
  作者：Keiichi Watanabe、Takashi Koshiba、Yoshitaka Yasufuku、Toshifumi Miyazawa、Shin-ichi Ueji

  DOI：10.1006/bioo.2000.1190

  日期：2001.4

  Substituent effects on the enantioselectivity for the lipase-catalyzed esterifications in organic solvents were studied by use of 2-(4-substituted phenoxy)propionic acids as the substrates with various substituents of H, F, Cl, CF(3), CH(3), CH(3)CH(2), and CH(3)O. The distinction in the behavior of their enantioselectivity was primarily responsible for the size effects of the substituents, although

  通过使用2-（4-取代的苯氧基）丙酸作为具有H，F，Cl，CF（3），CH（3）各种取代基的底物，研究了有机溶剂中取代酶对脂肪酶催化的酯化反应的对映选择性的影响。 ），CH（3）CH（2）和CH（3）O。尽管取代基远离底物的立体中心，但它们的对映选择性在行为上的区别主要是对取代基的尺寸效应的影响。对于大小相似的取代基CH（3）和CF（3），它们的电子效应在控制对映选择性中起着重要作用。基于获得的米氏常数（K（m））的值的讨论也支持由于电子效应引起的对映选择性的这种变化。此外，
• Enantioselective esterification of (RS)-2-(4-chlorophenoxy)propionic acid via Carica papaya lipase in organic solvents
  作者：Yu-Chi Cheng、Shau-Wei Tsai

  DOI：10.1016/j.tetasy.2004.05.036

  日期：2004.9

  the crude papain is found to be enantioselective for the kinetic resolution of (RS)-2-(4-chlorophenoxy)propionic acid via esterification in anhydrous organic solvents. Of the alcohols screened, trimethylsilylmethanol acted as the best acyl acceptor and gave the highest enzyme activity and enantioselectivity in anhydrous cyclohexane. The kinetic analysis at temperatures between 20 and 60 °C indicated

  发现在粗木瓜蛋白酶中储存的番木瓜脂肪酶（CPL）对（RS）-2-（4-氯苯氧基）丙酸在无水有机溶剂中的酯化反应动力学拆分具有对映选择性。在所筛选的醇中，三甲基甲硅烷基甲醇是最佳的酰基受体，在无水环己烷中具有最高的酶活性和对映选择性。在20至60°C的温度下进行的动力学分析表明CPL具有热稳定性，在20°C时具有113的高E值。将环己烷改为其他疏水性溶剂可产生更好的脂肪酶性能。与其他粗制念珠菌脂肪酶番木瓜的性能比较 脂肪酶具有更高的活性，对映选择性和热稳定性。
• Metal ions dramatically enhance the enantioselectivity for lipase-catalysed reactions in organic solvents
  作者：Takashi Okamoto、Ebara Yasuhito、Shin-ichi Ueji

  DOI：10.1039/b514885e

  日期：——

  simple and a powerful method to enhance the enantioselectivity for lipase-catalysed transformations in organic solvents by an addition of metal ion-containing water to the reaction mixture. In this paper, various metal ions such as LiCl or MgCl2 are tested to improve the enantioselectivity for the model reactions. The enantioselectivities obtained are dramatically enhanced, the E values of which are about

  我们提出了一种简单有效的方法，通过向反应混合物中添加含金属离子的水来增强对脂肪酶催化的有机溶剂转化的对映选择性。在本文中，对各种金属离子（如LiCl或MgCl2）进行了测试，以提高模型反应的对映选择性。所获得的对映选择性显着提高，与没有金属离子的普通条件（例如，通过添加LiCl的E = 200）相比，其E值约为100倍。此外，降低反应温度导致在金属离子存在下，例如通过添加LiCl，E ＝ 1300，脂肪酶的对映选择性几乎达到完美。还，
• Lyophilization of Lipase Together with Ionic Compounds Generates Highly Enantioselective and Solvent-sensitive Lipase in Organic Solvents
  作者：Shin-ichi Ueji、Shu-ichi Mori、Hiromi Yumoto、Naomi Hiroshima、Yasuhito Ebara

  DOI：10.1246/cl.2005.110

  日期：2005.1

  The lyophilization of lipase from aqueous enzyme solution containing ionic compounds such as disodium hydrogenphosphate resulted in a dramatic improvement of its enantioselectivity for esterification in organic solvents, compared with the ionic compound-free lipase. The enantioselectivity of the ionic compound-coated lipase was found to be fairly sensitive to the change of the solvents.

  从含有离子化合物（如磷酸氢二钠）的水相酶溶液中冻干的脂肪酶在有机溶剂中的酯化反应的对映选择性得到了显著提高，与不含离子化合物的脂肪酶相比。带有离子化合物涂层的脂肪酶的对映选择性对溶剂的变化相当敏感。