2-(4-异丙基苯氧基)丙酸 | 237412-04-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-异丙基苯氧基)丙酸
• 中文别名: 2-(2-硝基苯基)苯并噻唑
• 英文名称: (+/-)-2-(4-iso-propylphenoxy)propanoic acid
• 英文别名: 2-(4-Isopropylphenoxy)propanoic acid；2-(4-propan-2-ylphenoxy)propanoic acid
• CAS: 237412-04-3
• 化学式: C₁₂H₁₆O₃
• mdl: MFCD03422222
• 分子量: 208.257
• InChiKey: JQGMFMWLOKZVBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  323.2±25.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2918990090

反应信息

• 作为反应物：
  描述：

  2-(4-异丙基苯氧基)丙酸 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4-isopropylphenoxy) propanol
  参考文献：
  名称：

  Resolution of 2-aryloxy-1-propanols via lipase-catalyzed enantioselective acylation in organic media

  摘要：

  2-Aryloxy-1-propanols, primary alcohols with an oxygyen atom at the stereocenter. were resolved with good to high enantioselectivity by acylation with vinyl butanoate mediated by Pseudomonas sp. lipase in di-iso-propyl ether. Potential factors affecting the enantioselectivity of the enzymatic acylation were examined: solvents. acyl donors mid temperature, Using this enantioselective acylation procedure. enantiomeriocally pure (R)-2-(4-chlorophenoxy)-1-propanol was prepared on a grain scale. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00258-0

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。
• 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。
• Flexibility of Lipase Brought About by Solvent Effects Controls Its Enantioselectivity in Organic Media
  作者：Shin-ichi Ueji、Tomohiko Taniguchi、Takashi Okamoto、Keiichi Watanabe、Yasuhito Ebara、Hitoshi Ohta

  DOI：10.1246/bcsj.76.399

  日期：2003.2

  of the enantioselectivity of Candida rugosa lipase was investigated in the esterification of 2-(4-substituted phenoxy)propionic acids with 1-butanol in aliphatic, aromatic, and ethereal solvents. The observed enantioselectivity (E value) was greatly affected by the solvent nature. Two key solvent characteristics, dielectric constant (e) and hydrophobicity (log P), failed to explain the solvent effects

  2-（4-取代苯氧基）丙酸与 1-丁醇在脂肪族、芳香族和醚类溶剂中的酯化反应中研究了假丝酵母脂肪酶的对映选择性行为。观察到的对映选择性（E 值）受溶剂性质的影响很大。两个关键的溶剂特性，介电常数 (e) 和疏水性 (log P)，未能解释溶剂对 E 值的影响。另一方面，发现 E 值的变化与溶剂效应带来的脂肪酶灵活性成功相关，其灵活性是通过自旋标记脂肪酶的 ESR 测量来估计的。尽管有机化学家通常应该在生物催化不对称拆分中进行溶剂筛选步骤，
• Preparation of (R)-2-(4-hydroxyphenoxy) propionic acid by biotransformation
  作者：Christoph Dingler、Wolfgang Ladner、Georg A. Krei、Bryan Cooper、Bernhard Hauer

  DOI：10.1002/(sici)1096-9063(199601)46:1<33::aid-ps338>3.0.co;2-r

  日期：1996.1

  With Beauveria in bassiana Lu 700 as biocatalyst an ecologically beneficial process has been developed for the production of (R)-2-(4-hydroxyphenoxy) propionic acid. The fungal strain used in this process, B. bassiana Lu 700, is also a very suitable catalyst for the selective monohydroxylation of other aromatic carboxylic acids.