2-amino-N-(2-(benzylamino)-2-oxoethyl)acetamide hydrochloride | 1579198-56-3

• 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: 2-amino-N-(2-(benzylamino)-2-oxoethyl)acetamide hydrochloride
• 英文别名: 2-amino-N-[(benzylcarbamoyl)methyl]acetamide hydrochloride；2-amino-N-[2-(benzylamino)-2-oxoethyl]acetamide;hydrochloride
• CAS: 1579198-56-3
• 化学式: C₁₁H₁₅N₃O₂*ClH
• 分子量: 257.72
• InChiKey: MAABOXKTPYXGHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.2
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-amino-N-(2-(benzylamino)-2-oxoethyl)acetamide hydrochloride 在 三乙胺 作用下， 以 甲醇 、 氯仿 为溶剂， 以100 %的产率得到2-Amino-N-[(benzylcarbamoyl)methyl]acetamide
  参考文献：
  名称：

  N‐Terminal‐Specific Dual Modification of Peptides through Copper‐Catalyzed [3+2] Cycloaddition

  摘要：

  Site‐specific introduction of multiple components into peptides is greatly needed for the preparation of densely functionalized and structurally uniform peptides. In this regard, N‐terminal‐specific peptide modification is attractive, but it can be difficult due to the presence of highly nucleophilic lysine ϵ‐amine. In this work, we developed a method for the N‐terminal‐specific dual modification of peptides through a three‐component [3+2] cycloaddition with aldehydes and maleimides under mild copper catalysis. This approach enables exclusive functionalization at the glycine N‐terminus of iminopeptides, regardless of the presence of lysine ϵ‐amine, thus affording the cycloadducts in excellent yields. Tolerating a broad range of functional groups and molecules, the present method provides the opportunity to rapidly construct doubly functionalized peptides using readily accessible aldehyde and maleimide modules.

  DOI：

  10.1002/anie.202320012
• 作为产物：
  描述：

  Boc-Gly-Gly-NH-Bn 在 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 以97.8 %的产率得到2-amino-N-(2-(benzylamino)-2-oxoethyl)acetamide hydrochloride
  参考文献：
  名称：

  N‐Terminal‐Specific Dual Modification of Peptides through Copper‐Catalyzed [3+2] Cycloaddition

  摘要：

  Site‐specific introduction of multiple components into peptides is greatly needed for the preparation of densely functionalized and structurally uniform peptides. In this regard, N‐terminal‐specific peptide modification is attractive, but it can be difficult due to the presence of highly nucleophilic lysine ϵ‐amine. In this work, we developed a method for the N‐terminal‐specific dual modification of peptides through a three‐component [3+2] cycloaddition with aldehydes and maleimides under mild copper catalysis. This approach enables exclusive functionalization at the glycine N‐terminus of iminopeptides, regardless of the presence of lysine ϵ‐amine, thus affording the cycloadducts in excellent yields. Tolerating a broad range of functional groups and molecules, the present method provides the opportunity to rapidly construct doubly functionalized peptides using readily accessible aldehyde and maleimide modules.

  DOI：

  10.1002/anie.202320012

文献信息

• Novel <i>N</i>-transfer reagent for converting α-amino acid derivatives to α-diazo compounds
  作者：Guan-Han Lu、Tzu-Chia Huang、Hsiao-Chin Hsueh、Shin-Cherng Yang、Ting-Wei Cho、Ho-Hsuan Chou

  DOI：10.1039/d1cc01285a

  日期：——

  direct and effective transformation of α-amino ketones, acetamides, and esters to the corresponding α-diazo products under mild basic conditions has been developed. This one-step synthetic approach not only allows for generation of α-substituted-α-diazo carbonyl compounds from α-amino acid derivatives but also permits preparation of α-diazo dipeptides from N-terminal dipeptides (32 examples, up to 91%)

  开发了一种新型通用N-转移试剂，可在温和的碱性条件下直接有效地将 α-氨基酮、乙酰胺和酯转化为相应的 α-重氮产物。这种一步合成方法不仅允许从 α-氨基酸衍生物生成 α-取代-α-重氮羰基化合物，而且允许从N-末端二肽制备 α-重氮二肽（32 个例子，高达 91%） .