[(2S)-2-(trifluoromethyl)oxiran-2-yl]methyl butanoate | 1050669-71-0

• 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: [(2S)-2-(trifluoromethyl)oxiran-2-yl]methyl butanoate
• CAS: 1050669-71-0
• 化学式: C₈H₁₁F₃O₃
• 分子量: 212.169
• InChiKey: VCKDHFXWAKVKNZ-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(2S)-2-(trifluoromethyl)oxiran-2-yl]methyl butanoate 、 苄胺 生成 (S)-3,3,3-trifluoro-2-hydroxy-2-(((phenylmethyl)amino)methyl)propyl butanoate
  参考文献：
  名称：

  Efficient synthesis of an α-trifluoromethyl-α-tosyloxymethyl epoxide enabling stepwise double functionalisation to afford CF3-substituted tertiary alcohols

  摘要：

  The efficient synthesis of an alpha-trifluoromethyl-alpha-tosyloxymethyl epoxide is reported. This highly versatile building block may be reacted sequentially with two different nucleophiles to furnish alpha-trifluoromethyl tertiary alcohols. Furthermore, the two enantiomers of this key intermediate have been separated using chiral HPLC and the stereochemistry shown to be conserved during subsequent chemical manipulations. Finally, an enzyme-driven desymmetrisation approach has been successfully employed to confer chirality on an intermediate in the sequence. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.011
• 作为产物：
  描述：

  (R)-3,3,3-trifluoro-2-hydroxy-2({[(4-methylphenyl)sulfonyl]oxy}methyl)propyl butanoate 在 polymer-supported carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 [(2S)-2-(trifluoromethyl)oxiran-2-yl]methyl butanoate
  参考文献：
  名称：

  Efficient synthesis of an α-trifluoromethyl-α-tosyloxymethyl epoxide enabling stepwise double functionalisation to afford CF3-substituted tertiary alcohols

  摘要：

  The efficient synthesis of an alpha-trifluoromethyl-alpha-tosyloxymethyl epoxide is reported. This highly versatile building block may be reacted sequentially with two different nucleophiles to furnish alpha-trifluoromethyl tertiary alcohols. Furthermore, the two enantiomers of this key intermediate have been separated using chiral HPLC and the stereochemistry shown to be conserved during subsequent chemical manipulations. Finally, an enzyme-driven desymmetrisation approach has been successfully employed to confer chirality on an intermediate in the sequence. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.06.011