N-Phthaloylalanylglycine methyl ester | 21685-33-6

• 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-Phthaloylalanylglycine methyl ester
• 英文别名: Phthaloyl-DL-Ala-Gly-OCH3；Methyl 2-[2-(1,3-dioxoisoindol-2-yl)propanoylamino]acetate
• CAS: 21685-33-6
• 化学式: C₁₄H₁₄N₂O₅
• 分子量: 290.276
• InChiKey: XAASUSYDEFUYIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  92.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-Phthaloylalanylglycine 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 2.5h， 生成 N-Phthaloylalanyl-α-methoxyglycine 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：

  2-苯二甲酰亚氨基丙酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 N-Phthaloylalanylglycine methyl ester
  参考文献：
  名称：

  对甲氧基苄基自由基促进的仲烷基酰胺的化学选择性保护

  摘要：

  据报道，在铜催化下，使用对甲氧基苄基化烷基过氧化物作为新型对甲氧基苄基化试剂，对仲酰胺进行迄今困难的位点选择性对甲氧基苄基化。该反应在温和的反应条件下以高度化学选择性的方式进行。该方法已成功应用于肽的位点选择性对甲氧基苄基化。

  DOI：

  10.1021/acs.joc.2c02582

文献信息

• Regioselective functionalization of N-phthaloyl-substituted amino acid and peptide derivatives
  作者：Christopher J. Easton、Craig A. Hutton、Giovanna Rositano、Eng Wui Tan

  DOI：10.1021/jo00019a029

  日期：1991.9

  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.
• <i>p</i>-Methoxybenzyl-Radical-Promoted Chemoselective Protection of <i>sec</i>-Alkylamides
  作者：JingWen Jia、Terumasa Kato、Keiji Maruoka

  DOI：10.1021/acs.joc.2c02582

  日期：2023.2.17

  The hitherto difficult site-selective p-methoxybenzylation of secondary amides using p-methoxybenzylated alkylsilyl peroxides as a novel p-methoxybenzylation agent under copper catalysis is reported. The reaction proceeds under mild reaction conditions in a highly chemoselective manner. This approach was successfully applied to the site-selective p-methoxybenzylation of peptides.

  据报道，在铜催化下，使用对甲氧基苄基化烷基过氧化物作为新型对甲氧基苄基化试剂，对仲酰胺进行迄今困难的位点选择性对甲氧基苄基化。该反应在温和的反应条件下以高度化学选择性的方式进行。该方法已成功应用于肽的位点选择性对甲氧基苄基化。