(S)-p-(2,2,2-trifluoro-1-hydroxyethyl)benzoic acid | 130534-97-3

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 环羧酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-p-(2,2,2-trifluoro-1-hydroxyethyl)benzoic acid
• 英文别名: (S)-4-(2,2,2-trifluoro-1-hydroxyethyl)benzoic acid；4-[(1S)-2,2,2-Trifluoro-1-hydroxyethyl]benzoic acid
• CAS: 130534-97-3
• 化学式: C₉H₇F₃O₃
• 分子量: 220.148
• InChiKey: XIFJNKHTLXGSPU-ZETCQYMHSA-N

物化性质

• 沸点：
  342.8±42.0 °C(Predicted)
• 密度：
  1.473±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(2,2,2-三氟乙酰)苯甲酸 在 Almag CRED A₁₆₁ 、 NADP 、 glucose dehydrogenase 作用下， 以 水 、 二甲基亚砜 、 异丙醇 为溶剂， 35.0 ℃ 、50.0 kPa 条件下， 以78%的产率得到(S)-p-(2,2,2-trifluoro-1-hydroxyethyl)benzoic acid
  参考文献：
  名称：

  Preparative access to medicinal chemistry related chiral alcohols using carbonyl reductase technology

  摘要：

  Libraries of highly enantioenriched secondary alcohols in both enantiomeric forms were synthesised by enzymatic reduction of their parent ketones using selectAZyme (TM) carbonyl reductase (CRED) technology. Commercially available CREDs were able to reduce a range of substrate classes efficiently and with very high enantioselectivity. Matching substrate classes to small subsets of CREDs enabled the fast development of preparative bioreductions and the rapid generation of 100-1500 mg samples of chiral alcohols in typically >95% ee and the majority in >= 99.0% ee. The conditions for small scale synthesis were then scaled up to 0.5 kg to deliver one of the chiral alcohols, (S)-1-(4-bromophenyl)-2-chloroethanol, in 99.8% ee and 91% isolated yield. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.09.015

文献信息

• Stereocontrolled synthesis of p-substituted trifluoromethylbenzylic alcohol derivatives of high optical purity by the baker's yeast reduction
  作者：Tamotsu Fujisawa、Kouji Ichikawa、Makoto Shimizu

  DOI：10.1016/s0957-4166(00)80234-7

  日期：1993.6

  enantioselectivity of the bakers' yeast reduction of p-substituted trifluoroacetylbenzene derivatives could be improved by the introduction of some functional groups at the para-position to give the corresponding (R)-trifluoromethyl-substituted benzylic alcohols in high chemical and optical yields. The optically active alcohols obtained were readily converted into optically pure forms by recrystallization

  通过在对位引入一些官能团可以提高面包师酵母还原对位取代的三氟乙酰苯衍生物的对映选择性，从而以高化学和光学收率得到相应的（R）-三氟甲基取代的苄醇。所获得的旋光性醇易于通过重结晶转化成旋光纯净的形式。