2,2,2-Trifluor-1-ethansulfonyl-N-benzoyl-ethylamin | 1464-85-3

• 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: 2,2,2-Trifluor-1-ethansulfonyl-N-benzoyl-ethylamin
• 英文别名: N-(1-ethylsulfonyl-2,2,2-trifluoroethyl)benzamide
• CAS: 1464-85-3
• 化学式: C₁₁H₁₂F₃NO₃S
• 分子量: 295.282
• InChiKey: YUYZFRHMASWSEV-UHFFFAOYSA-N

物化性质

• 熔点：
  171 °C
• 沸点：
  472.0±45.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  63.24
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2,2,2-Trifluor-1-ethansulfonyl-N-benzoyl-ethylamin 在 氢氧化钾 作用下， 以 四氢呋喃 为溶剂， 生成 2,2,2,2',2',2'-Hexafluor-1,1'-dibenzamino-diethylether
  参考文献：
  名称：

  Weygand,F.; Steglich,W., Chemische Berichte, 1965, vol. 98, p. 487 - 503

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2,2-Trifluor-1-ethylmercapto-N-benzoyl-ethylamin 在 双氧水 、 乙酸酐 作用下， 反应 48.0h， 以16.1 g的产率得到2,2,2-Trifluor-1-ethansulfonyl-N-benzoyl-ethylamin
  参考文献：
  名称：

  Design of Radical-Resistant Amino Acid Residues:  A Combined Theoretical and Experimental Investigation

  摘要：

  Ab initio calculations have been used to design radical-resistant amino acid residues. Optimized structures of free and protected amino acids and their corresponding alpha-carbon-centered radicals were determined with B3-LYP/6-31G(d). Single-point RMP2/6-31G(d) calculations on these structures were then used to obtain radical stabilization energies, to examine the effect of steric repulsion between the side chains and amide carbonyl groups on the stability of alpha-carbon-centered peptide radicals. Relative to glycine, the destabilization for alanine and valine residues was found to be approximately 9 and 18 kJ mol(-1), respectively, which correlates with the reactivity of analogous amino acid residues in peptides toward hydrogen atom abstraction in conventional free radical reactions. To design amino acid residues that would resist radical reactions, strategies by which the steric effects could be magnified were considered. This resulted in the identification of tert-leucine and 3,3,3-trifluoroalanine as suitable molecules. With these amino acid residues, the destabilization of the alpha-carbon-centered radicals relative to that of glycine is increased substantially to approximately 36 and 41 kJ mol(-1), respectively. The theoretical predictions have been supported by experimental observations: a tert-leucine derivative was shown to be very slow to react with N-bromosuccinimide, while the corresponding trifluoroalanine derivative was found to be inert.

  DOI：

  10.1021/ja029674v

文献信息

• Weygand,F. et al., Chemische Berichte, 1966, vol. 99, p. 1932 - 1943
  作者：Weygand,F. et al.

  DOI：——

  日期：——
• Weygand,F. et al., Zeitschrift fur Naturforschung. Teil B. Anorganische Chemie, organische Chemie, Biochemie, Biophysik, Biologie, 1966, vol. 21, p. 467 - 471
  作者：Weygand,F. et al.

  DOI：——

  日期：——