2-hydroxy-2-(trifluoromethyl)butyric acid methyl ester | 114645-37-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-hydroxy-2-(trifluoromethyl)butyric acid methyl ester
• 英文别名: methyl 2-hydroxy-2-trifluoromethylbutanoate；Methyl 2-hydroxy-2-(trifluoromethyl)butanoate
• CAS: 114645-37-3
• 化学式: C₆H₉F₃O₃
• 分子量: 186.131
• InChiKey: WKMZMJQTDGMZNB-UHFFFAOYSA-N

物化性质

• 沸点：
  92-93 °C(Press: 270 Torr)
• 密度：
  1.283±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-hydroxy-2-(trifluoromethyl)butyric acid methyl ester 在 盐酸 作用下， 反应 10.0h， 以76%的产率得到2-hydroxy-2-trifluoromethylbutanoic acid
  参考文献：
  名称：

  Soloshonok, V. A.; Gerus, I. I.; Yagupol'skii, Yu. L., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1298 - 1303

  摘要：

  DOI：
• 作为产物：
  描述：

  2-hydroxy-2-trifluoromethylbutanoic acid 、 原甲酸三甲酯 在 甲醇 、 硫酸 作用下， 反应 4.0h， 以81%的产率得到2-hydroxy-2-(trifluoromethyl)butyric acid methyl ester
  参考文献：
  名称：

  The synthesis of (R)- and (S)-α-trifluoromethyl-α-hydroxycarboxylic acids via enzymatic resolutions

  摘要：

  Kinetic resolution of 1,1,1-trifluoro-2-alkanone cyanohydrin acyl derivatives with Candida rugosa lipase afforded the remaining (R)-enantiomer in high selectivity (E from 30 to >200). Candida rugosa lipases from several suppliers were compared and found to differ remarkably in their selectivity. The (R)-enantiomer was hydrolyzed in one step to yield optically pure (R)-alpha-trifluoromethyl-alpha-hydroxycarboxylic acids in excellent yield. The (S)-acids were obtained in good e.e. by subtilisin-catalyzed resolution of the corresponding racemic esters followed by chemical hydrolysis of the remaining (S)-esters. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00017-8

文献信息

• Cyclocondensation of trifluorolactates with isocyanates
  作者：V. B. Sokolov、A. Yu. Aksinenko、T. A. Epishina、T. V. Goreva、I. V. Martynov

  DOI：10.1007/s11172-013-0134-x

  日期：2013.4

  Cyclocondensation of trifluorolactates with isocyanates gives 3-substituted 5-trifluoromethyloxazolidine-2,4-diones.

  三氟乳酸酯与异氰酸酯的环缩合得到3-取代的5-三氟甲基恶唑烷-2,4-二酮。
• Process for preparing optically active 3,3,3- trifluoromethyl-2-alkylpropionic acid derivatives
  申请人：LONZA AG

  公开号：US20020039769A1

  公开（公告）日：2002-04-04

  The invention relates to a novel method for the preparation of optically active 3,3,3-trifluoromethyl-2-alkylpropionic acid derivatives of the general formulae (I) and (II), in which R is ethyl or methyl and X is OH or NH 2 , provided that if R is methyl X≠—OH. The method comprises the reaction of a racemic propionic acid amide of the general formula (III) either by means of microorganisms which are able to use the propionic acid amide in the form of the racemate or one of its optically active isomers as the only nitrogen source or by means of a polypeptide with amidohydrolase activity which is able to hydrolyze the propionic acid amide. The invention also relates to new optically active representatives of this category of compounds.

  本发明涉及一种制备光学活性的3,3,3-三氟甲基-2-烷基丙酸衍生物的新方法，其通式为(I)和(II)，其中R为乙基或甲基，X为OH或NH2，但如果R为甲基，则X≠-OH。该方法包括通过微生物反应或具有酰胺水解酶活性的多肽水解酰胺的方式反应通式(III)的外消旋丙酸酰胺，其中微生物能够将外消旋体或其光学异构体之一作为唯一的氮源。本发明还涉及该类化合物的新的光学活性代表。
• SOLOSHONOK, V. A.;GERUS, I. I.;YAGUPOLSKIJ, YU. L.;KUXAR, V. P., ZH. ORGAN. XIMII, 23,(1987) N 7, 1441-1447
  作者：SOLOSHONOK, V. A.、GERUS, I. I.、YAGUPOLSKIJ, YU. L.、KUXAR, V. P.

  DOI：——

  日期：——
• Soloshonok, V. A.; Gerus, I. I.; Yagupol'skii, Yu. L., Journal of Organic Chemistry USSR (English Translation), 1987, vol. 23, # 7, p. 1298 - 1303
  作者：Soloshonok, V. A.、Gerus, I. I.、Yagupol'skii, Yu. L.、Kukhar', V. P.

  DOI：——

  日期：——
• The synthesis of (R)- and (S)-α-trifluoromethyl-α-hydroxycarboxylic acids via enzymatic resolutions
  作者：Kurt Konigsberger、Kapa Prasad、Oljan Repič

  DOI：10.1016/s0957-4166(99)00017-8

  日期：1999.2

  Kinetic resolution of 1,1,1-trifluoro-2-alkanone cyanohydrin acyl derivatives with Candida rugosa lipase afforded the remaining (R)-enantiomer in high selectivity (E from 30 to >200). Candida rugosa lipases from several suppliers were compared and found to differ remarkably in their selectivity. The (R)-enantiomer was hydrolyzed in one step to yield optically pure (R)-alpha-trifluoromethyl-alpha-hydroxycarboxylic acids in excellent yield. The (S)-acids were obtained in good e.e. by subtilisin-catalyzed resolution of the corresponding racemic esters followed by chemical hydrolysis of the remaining (S)-esters. (C) 1999 Elsevier Science Ltd. All rights reserved.