butyl 2-(4-isobutylphenyl)propanoate | 64622-49-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: butyl 2-(4-isobutylphenyl)propanoate
• 英文别名: Ibuprofen butyl；butyl 2-[4-(2-methylpropyl)phenyl]propanoate
• CAS: 64622-49-7
• 化学式: C₁₇H₂₆O₂
• 分子量: 262.392
• InChiKey: JMYISEMZJYEMCF-UHFFFAOYSA-N

物化性质

• 沸点：
  337.4±11.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)
• 保留指数：
  1452

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  butyl 2-(4-isobutylphenyl)propanoate 在 Candida rugosa lipase type VII lyophilized from aqueous solution 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 布洛芬
  参考文献：
  名称：

  使用共溶剂作为添加剂大大提高脂肪酶催化水解和酯化的对映选择性

  摘要：

  添加共溶剂如四氢呋喃导致脂肪酶催化的 2-(4-取代苯氧基)丙酸丁酯在缓冲水溶液中水解的对映选择性大大提高。另一方面，从含有共溶剂的水溶液中冻干的脂肪酶催化 2-（4-取代苯氧基）丙酸、2-（4-异丁基苯基）丙酸（布洛芬）和 2-（6 -甲氧基-2-萘基）丙酸（萘普生）在有机溶剂中。对于某些底物，观察到 E 值增加了两个数量级。由共溶剂添加引起的对映选择性增强的起源主要归因于错误结合的对映异构体的初始反应速率显着减慢，与正确结合的对映体相比。从FT-IR、CD和ESR光谱的结果来看，还发现共溶剂的加入导致脂肪酶三级结构的部分破坏。

  DOI：

  10.1246/bcsj.81.617
• 作为产物：
  描述：

  布洛芬 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 butyl 2-(4-isobutylphenyl)propanoate
  参考文献：
  名称：

  Trichosporon beigelli esterase (TBE): a versatile esterase for the resolution of economically important racemates

  摘要：

  A hydrolase producing strain Trichosporon beigelli esterase (TBE) isolated from local cottage cheese in its native form has displayed versatility and high efficacy in the kinetic resolution of a wide range of economically important substrates, which include racemic secondary alcohols, such as 1-(6-methoxy-2-naphtliyl)ethanol (E similar to 316), 1-(3,4-methylenedioxyphenyl)ethanol and pentanol (E similar to 180 and 156 resp.), and alkyl esters of carboxylic acids such as ibuprofen (E similar to 340), 2-(benzylthio)propanoic acid (E similar to 1000). In other substrates such as in the primary alcohol 2-(6-methoxy-2-naphthyl)propan-1-ol and carboxylic acids such as 2-(5-bromo-6-methoxy-2-naphthyl)propanoic acid, 2-(2-naphthyloxy)propanoic acid, and substituted 2-thiopropanoic acids, it displayed moderate to low selectivity. Commercial lipases such as CCL, PPL, and PSL were also used in the resolution of the substrates for comparative studies. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.07.009

文献信息

• Protic Acid Immobilized on Solid Support as an Extremely Efficient Recyclable Catalyst System for a Direct and Atom Economical Esterification of Carboxylic Acids with Alcohols
  作者：Asit K. Chakraborti、Bavneet Singh、Sunay V. Chankeshwara、Alpesh R. Patel

  DOI：10.1021/jo900614s

  日期：2009.8.21

  reported by direct condensation of equimolar amounts of carboxylic acids with alcohols catalyzed by an easy to prepare catalyst system of perchloric acid immobilized on silica gel (HClO4−SiO2). The direct condensation of aryl, heteroaryl, styryl, aryl alkyl, alkyl, cycloalkyl, and long-chain aliphatic carboxylic acids with primary/secondary alkyl/cycloalkyl, allyl, propargyl, and long-chain aliphatic alcohols

  据报道，通过容易制备的固定在硅胶上的高氯酸催化剂体系（HClO 4 -SiO 2）催化等摩尔量的羧酸与醇的直接缩合，酯化反应既方便又清洁。已经实现了芳基，杂芳基，苯乙烯基，芳基烷基，烷基，环烷基和长链脂族羧酸与伯/仲烷基/环烷基，烯丙基，炔丙基和长链脂族醇的直接缩合以提供相应的酯高产。手性醇和N - t- Boc保护的手性氨基酸也导致与代表性的羧酸或醇形成酯，而没有竞争性的N - t-Boc对产品的光学纯度的脱保护和有害作用，表明该方法的温和性和化学选择性。长链（> C 10）酸和醇的酯以高收率获得。催化剂被回收和再循环而没有明显的活性损失。酯化工艺的工业应用通过布洛芬前药和几种商业调味剂的合成得到证明。其他质子酸如H 2 SO 4，HBr的，TfOH，HBF 4相比的HClO和TFA被吸附在硅胶上的是不太有效4 -SiO 2以下的顺序的HClO 4 -SiO 2 »ħ 2SO 4 -SiO
• One-Pot Esterification and Amide Formation via Acid-Catalyzed Dehydration and Ritter Reactions
  作者：Pankaj Dawar、M. Bagavan Raju、Ramesha Andagar Ramakrishna

  DOI：10.1080/00397911.2013.837485

  日期：2014.3.19

  Esterification of carboxylic acid is achieved using acetonitrile as a water trap. Water liberated during esterification is consumed in cyanide hydrolysis, thereby driving the esterification to completion. Substrates having carboxylic acid and nitrile groups undergo intramolecular dehydration and rehydration to amido esters in the absence of acetonitrile. Cyano acids also undergo esterification and Ritter reaction in one pot when excess alcohol is used. For the first time, we have observed an interesting Ritter reaction of primary alcohols, leading to ester amide product in one pot. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Bansal; Khar; Dubey, Pharmazie, 1994, vol. 49, # 6, p. 422 - 424
  作者：Bansal、Khar、Dubey、Sharma

  DOI：——

  日期：——
• A method to greatly improve the enantioselectivity of lipase-catalyzed hydrolysis using sodium dodecyl sulfate (SDS) as an additive
  作者：Shuichi Mori、Hiromi Yumoto、Rina Matsumi、Tomohiro Nishigaki、Yasuhito Ebara、Shin-ichi Ueji

  DOI：10.1016/j.tetasy.2005.10.003

  日期：2005.11

  The addition of sodium dodecyl sulfate (SDS) resulted in a dramatic improvement of the enantioselectivity of the lipasecatalyzed hydrolysis of racemic butyl 2-(4-substituted phenoxy)propanoates, racemic butyl 2-(4-isobutylphenyl)propanoate, and racemic butyl 2-(6-methoxy-2-naphthyl)propanoate in an aqueous buffer solution. An increase in the E value by up to two orders of magnitude was observed for some esters. As to the effects of SDS on the structure of a lipase, FT-IR and fluorescence measurements suggest some conformational change and/or an increase of the flexibility of the lipase, although the native secondary structure of the lipase is held even in the presence of 100 mM SDS. The origin of the enantioselectivity enhancement brought about by the addition of SDS is briefly discussed on the basis of the values of the initial rates obtained for each enantiomer of the substrate. (c) 2005 Elsevier Ltd. All rights reserved.
• Shunmugadhas, Ganesan; Kumar, Suresh; Kumaresan, Sudalaiandi, Journal of Chemical Sciences, 2012, vol. 124, # 4, p. 857 - 863,7
  作者：Shunmugadhas, Ganesan、Kumar, Suresh、Kumaresan, Sudalaiandi

  DOI：——

  日期：——