Bromo-{2-bromo-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-acetylamino}-acetic acid methyl ester | 135395-24-3

• 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: Bromo-{2-bromo-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-acetylamino}-acetic acid methyl ester
• 英文别名: Methyl 2-bromo-2-[[2-bromo-2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]acetyl]amino]acetate；methyl 2-bromo-2-[[2-bromo-2-[[2-(1,3-dioxoisoindol-2-yl)acetyl]amino]acetyl]amino]acetate
• CAS: 135395-24-3
• 化学式: C₁₅H₁₃Br₂N₃O₆
• 分子量: 491.093
• InChiKey: LSBGFGROVOCAMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  122
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Bromo-{2-bromo-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-acetylamino}-acetic acid methyl ester 在 氘代三正丁基锡 作用下， 以 二氯甲烷 为溶剂， 生成 N-Phthaloylglycyl-α-deuterioglycyl-α-deuterioglycine methyl ester
  参考文献：
  名称：

  Regioselective functionalization of N-phthaloyl-substituted amino acid and peptide derivatives

  摘要：

  The free-radical reactions of a range of amino acid derivatives with N-bromosuccinimide are described. The products and relative rates of these reactions indicate that the alpha-position of an N-phthaloyl-substituted alpha-amino acid derivative is much less reactive than that of a corresponding N-acyl amino acid derivative toward hydrogen atom transfer. This is attributed to the proactive effects of acylamino and carboxyl substituents, in contrast to the counteractive effects of phthalimido and carboxyl groups. The reactions exemplify procedures for the regiocontrolled functionalization of amino acid and peptide derivatives.

  DOI：

  10.1021/jo00019a029
• 作为产物：
  描述：

  N-Phthaloylglycylglycylglycine methyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Bromo-{2-bromo-2-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetylamino]-acetylamino}-acetic acid methyl ester
  参考文献：
  名称：

  Regioselective functionalization of N-phthaloyl-substituted amino acid and peptide derivatives

  摘要：

  The free-radical reactions of a range of amino acid derivatives with N-bromosuccinimide are described. The products and relative rates of these reactions indicate that the alpha-position of an N-phthaloyl-substituted alpha-amino acid derivative is much less reactive than that of a corresponding N-acyl amino acid derivative toward hydrogen atom transfer. This is attributed to the proactive effects of acylamino and carboxyl substituents, in contrast to the counteractive effects of phthalimido and carboxyl groups. The reactions exemplify procedures for the regiocontrolled functionalization of amino acid and peptide derivatives.

  DOI：

  10.1021/jo00019a029