N-benzoyl-2,3-dibromovaline methyl ester | 98517-04-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzoyl-2,3-dibromovaline methyl ester
• 英文别名: methyl 2-benzamido-2,3-dibromo-3-methylbutanoate
• CAS: 98517-04-5
• 化学式: C₁₃H₁₅Br₂NO₃
• 分子量: 393.075
• InChiKey: MQFQQAIDAJWFGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 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：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2,3-dibromovaline methyl ester 在 吡啶 作用下， 反应 0.5h， 以64%的产率得到methyl 2-benzamido-3-methylbut-2-enoate
  参考文献：
  名称：

  Easton, Christopher J.; Hay, Michael P.; Love, Stephen G., Journal of the Chemical Society. Perkin transactions I, 1988, p. 265 - 268

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R)-2-(benzoylamino)-3-methylbutyric acid methyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 生成 N-benzoyl-2,3-dibromovaline methyl ester
  参考文献：
  名称：

  Selective reaction of glycine residues in hydrogen atom transfer from amino acid derivatives

  摘要：

  DOI：

  10.1021/ja00185a039

文献信息

• Preferential reactivity of glycine residues in free radical reactions of amino acid derivatives
  作者：Christopher J. Easton、Michael P. Hay

  DOI：10.1039/c39860000055

  日期：——

  Reactions of amino acid derivatives, including a novel synthetic procedure for direct and selective functionalisation of glycine derivatives, indicate that the particular reactivity of glycine residues in free radical reactions is due to the stability of the radicals produced by their atom transfer reactions.

  氨基酸衍生物的反应，包括用于甘氨酸衍生物的直接和选择性官能化的新颖合成方法，表明甘氨酸残基在自由基反应中的特定反应性是由于其原子转移反应产生的自由基的稳定性。
• Design of Radical-Resistant Amino Acid Residues:  A Combined Theoretical and Experimental Investigation
  作者：Anna K. Croft、Christopher J. Easton、Leo Radom

  DOI：10.1021/ja029674v

  日期：2003.4.1

  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.
• EASTON, CHRISTOPHER J.;HAY, MICHAEL P.;LOVE, STEPHEN G., J. CHEM. SOC. PERKIN TRANS.,(1988) N 2, 265-268
  作者：EASTON, CHRISTOPHER J.、HAY, MICHAEL P.、LOVE, STEPHEN G.

  DOI：——

  日期：——