Ethyl 2-(4-isopropylphenyl)propanoate | 58929-93-4

• 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: Ethyl 2-(4-isopropylphenyl)propanoate
• 英文别名: ibuprofen ethyl ester；Ethyl 2-(4-propan-2-ylphenyl)propanoate
• CAS: 58929-93-4
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: YFBWRICIDLETDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  Ethyl 2-(4-isopropylphenyl)propanoate 在 native lipase from Candida rugosa 、 水 作用下， 生成 (S)-2-(4'-isopropylphenyl) propionic acid
  参考文献：
  名称：

  化学酶法合成纯对映体2-芳基丙酸。

  摘要：

  描述了一种获得纯对映体2-芳基丙酸的新化学酶法。一锅合成（±）-2-芳基丙酸是通过将二氯卡宾加成至芳基甲基酮的O键并加成产物进行氢解来进行的。外消旋混合物通过使用来自假丝酵母的天然脂肪酶的外消旋乙酯的对映体特异性水解来拆分。良好的收率，起始的芳基甲基酮的可及性和酶促水解的立体特异性使该方法变得有趣，以便获得相同的非甾体类抗炎药，如布洛芬或萘普生。

  DOI：

  10.1016/s0040-4020(01)81926-8
• 作为产物：
  描述：

  (S)-ibuprofen ethyl ester 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 甲基叔丁基醚 为溶剂， 反应 8.0h， 生成 Ethyl 2-(4-isopropylphenyl)propanoate
  参考文献：
  名称：

  Organocatalytic Racemization of α-Aryl Propionates in the Presence of Water

  摘要：

  An organocatalytic method for the racemization of alpha-aryl propionates, which proceeds even in the presence of an aqueous phase, has been developed, thus fulfilling a prerequisite for a dynamic kinetic resolution of corresponding esters with hydrolase as a biocatalyst. The desired racemization of ethyl 2-phenylpropionate and 2-ibuprofen ethyl ester as substrates has been achieved in a two-phase system. As preferred organocatalysts for the racemization, 1,8-diazabicyclo[5.4.0] undec-7-ene and 1,5,7-triazabicyclo[4.4.0] dec-5-ene (TBD) have been used.

  DOI：

  10.1080/00397911.2011.587081

文献信息

• Abd-El-Aziz, Alaa S.; Boraie, Waleed; Al-Salem, Najceb, Journal of the Chemical Society. Perkin transactions I, 1997, # 10, p. 1469 - 1479
  作者：Abd-El-Aziz, Alaa S.、Boraie, Waleed、Al-Salem, Najceb、Sadek, Salwa A.、Epp, Karen M.

  DOI：——

  日期：——
• Organocatalytic Racemization of <font>α</font>-Aryl Propionates in the Presence of Water
  作者：Maria Alfaro Blasco、Harald Gröger

  DOI：10.1080/00397911.2011.587081

  日期：2013.1.1

  An organocatalytic method for the racemization of alpha-aryl propionates, which proceeds even in the presence of an aqueous phase, has been developed, thus fulfilling a prerequisite for a dynamic kinetic resolution of corresponding esters with hydrolase as a biocatalyst. The desired racemization of ethyl 2-phenylpropionate and 2-ibuprofen ethyl ester as substrates has been achieved in a two-phase system. As preferred organocatalysts for the racemization, 1,8-diazabicyclo[5.4.0] undec-7-ene and 1,5,7-triazabicyclo[4.4.0] dec-5-ene (TBD) have been used.
• Chemoenzymatic synthesis of pure enantiomeric 2-aryl propionic acids.
  作者：Mariano García、Carmen del Campo、Emilio F. lama、José M. Sánchez-Montero、José V. Sinisterra

  DOI：10.1016/s0040-4020(01)81926-8

  日期：1993.1

  A new chemoenzymatic procedure to obtain pure enantiomeric 2-arylpropionic acids is described. The one pot synthesis of (±)-2-arylpropionic acids is carried out by addition of dichlorocarbene to the O bond of arylmethylketones and hydrogenolysis of the addition product. The racemic mixture is resolved by enantiospecific hydrolysis of the racemic ethyl esters using native lipase from Candida rugosa

  描述了一种获得纯对映体2-芳基丙酸的新化学酶法。一锅合成（±）-2-芳基丙酸是通过将二氯卡宾加成至芳基甲基酮的O键并加成产物进行氢解来进行的。外消旋混合物通过使用来自假丝酵母的天然脂肪酶的外消旋乙酯的对映体特异性水解来拆分。良好的收率，起始的芳基甲基酮的可及性和酶促水解的立体特异性使该方法变得有趣，以便获得相同的非甾体类抗炎药，如布洛芬或萘普生。