trifluorolactic acid isopropyl ester | 149526-95-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: trifluorolactic acid isopropyl ester
• 英文别名: isopropyl 3,3,3-trifluoro-2-hydroxypropanoate；isopropyl 3,3,3-trifluorolactate；(R,S)-isopropyl 3,3,3-trifluoro-2-hydroxypropanoate；(R,S)-isopropyl 3,3,3-(trifluoro)lactate；Propan-2-yl 3,3,3-trifluoro-2-hydroxypropanoate；propan-2-yl 3,3,3-trifluoro-2-hydroxypropanoate
• CAS: 149526-95-4
• 化学式: C₆H₉F₃O₃
• 分子量: 186.131
• InChiKey: PWDQWZKGRJRHSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：

  trifluorolactic acid isopropyl ester 生成 (S)-isopropyl 3,3,3-trifluoro-2-hydroxypropanoate
  参考文献：
  名称：

  对映异构体及其外消旋体的蒸馏分离：三氟乳酸酯的强手性识别能力

  摘要：

  三氟乳酸酯通过分馏对其对映体过量进行了修饰。定量研究表明，对映体与其外消旋体的分离是由于沸点的变化，这取决于化合物的对映体过量。在非氟化乳酸盐的情况下，没有看到沸点的这种变化。

  DOI：

  10.1246/cl.1996.115
• 作为产物：
  描述：

  3,3,3-三氟乳酸 、 异丙醇 在 硫酸 作用下， 反应 24.0h， 生成 trifluorolactic acid isopropyl ester
  参考文献：
  名称：

  Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition

  摘要：

  The presented results convincingly demonstrate that self-disproportionation of enantiomers via sublimation is substantially more complex phenomenon then was previously believed. We demonstrate that the racemic form of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate (1) sublimed faster regardless of the starting enantiomeric composition of the enantiomerically enriched mixtures studied in the range from 20.8, 36.8, 58.7 to 79.4% ee. This preferential sublimation of the racemic form allowed for, the most possibly simple, preparation of optically pure samples of compound 1. In this work we also suggest some general experimental procedures, which may be easily used to facilitate the interpretation of the data collected in different laboratories. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.11.026

文献信息

• Uncatalyzed Meerwein–Ponndorf–Verley reduction of trifluoromethyl carbonyl compounds by high-temperature secondary alcohols
  作者：Sergei A. Lermontov、Sergei V. Shkavrov、Nina V. Kuryleva

  DOI：10.1016/s0022-1139(03)00036-8

  日期：2003.6

  Noncatalytic Meerwein–Ponndorf–Verley (MPV) reduction of hexafluoroacetone and methyl ester of trifluoropyruvic acid into hexafluoroisopropanol (HFIP) and trifluorolactic esters, respectively can be achieved by heating with secondary alcohols at 210–250 °C without any catalyst.

  通过在210-250°C的条件下与仲醇加热，无需任何催化剂，即可将六氟丙酮和三氟丙酮酸的甲基酯分别无催化Meerwein-Ponndorf-Verley（MPV）还原成六氟异丙醇（HFIP）和三氟乳酸酯。
• JPH069497A
  申请人：——

  公开号：JPH069497A

  公开（公告）日：1994-01-18
• Self-disproportionation of enantiomers of isopropyl 3,3,3-(trifluoro)lactate via sublimation: Sublimation rates vs. enantiomeric composition
  作者：Manabu Yasumoto、Hisanori Ueki、Taizo Ono、Toshimasa Katagiri、Vadim A. Soloshonok

  DOI：10.1016/j.jfluchem.2009.11.026

  日期：2010.4

  The presented results convincingly demonstrate that self-disproportionation of enantiomers via sublimation is substantially more complex phenomenon then was previously believed. We demonstrate that the racemic form of isopropyl 3,3,3-trifluoro-2-hydroxypropanoate (1) sublimed faster regardless of the starting enantiomeric composition of the enantiomerically enriched mixtures studied in the range from 20.8, 36.8, 58.7 to 79.4% ee. This preferential sublimation of the racemic form allowed for, the most possibly simple, preparation of optically pure samples of compound 1. In this work we also suggest some general experimental procedures, which may be easily used to facilitate the interpretation of the data collected in different laboratories. (C) 2009 Elsevier B.V. All rights reserved.
• Separation of an Enantiomorph and Its Racemate by Distillation: Strong Chiral Recognizing Ability of Trifluorolactates
  作者：Toshimasa Katagiri、Chika Yoda、Keizo Furuhashi、Katsuyuki Ueki、Toshio Kubota

  DOI：10.1246/cl.1996.115

  日期：1996.2

  Trifluorolactate experienced modification of its enantiomeric excess by fractional distillation. Quantitative studies have shown that the separation of an enantiomorph and its racemate is due to a change in boiling points that depend on the enantiomeric excess of the compound. Such a change in the boiling point was not seen in the case of the non fluorinated lactate.

  三氟乳酸酯通过分馏对其对映体过量进行了修饰。定量研究表明，对映体与其外消旋体的分离是由于沸点的变化，这取决于化合物的对映体过量。在非氟化乳酸盐的情况下，没有看到沸点的这种变化。