N-tert-butyl-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide | 1068966-91-5

• 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: N-tert-butyl-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide
• CAS: 1068966-91-5
• 化学式: C₁₃H₁₆F₃NO₂
• 分子量: 275.271
• InChiKey: NWIDRBGHDIMHSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-(tert-butylamino)-1,1,1-trifluoro-3-oxo-2-phenylpropan-2-yl acetate 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以67%的产率得到N-tert-butyl-3,3,3-trifluoro-2-hydroxy-2-phenylpropanamide
  参考文献：
  名称：

  Hydrolase-catalyzed stereoselective preparation of protected α,α-dialkyl-α-hydroxycarboxylic acids

  摘要：

  The title compounds were prepared by a Passerini multi-component reaction and subjected to enzymatic kinetic resolution using 40 enzymes known to be active towards esters of tertiary alcohols. This identified a protease (P]), a thermophilic esterase (PestE) and an esterase of metagenome origin (esterase 8) as the most active and enantioselective biocatalysts. After further optimization of reaction conditions, two compounds were prepared in preparative scale using esterase 8 yielding (+)-1-(tert-butylamino)-2-methyl-l-oxobutyl-2-yl acetate with 93%ee and (-)-1-(tert-butylamino)-2-trifluofo-methyl-1-oxobutyl-2-yl acetate with 47%ee. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.005