2-((6S,9aR)-1-(2-aminophenyl)-6-benzyl-4,7-dioxohexahydro-1H-pyrazino[1,2-a]pyrimidin-8(2H)-yl)acetamide | 1417604-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-((6S,9aR)-1-(2-aminophenyl)-6-benzyl-4,7-dioxohexahydro-1H-pyrazino[1,2-a]pyrimidin-8(2H)-yl)acetamide
• CAS: 1417604-39-7
• 化学式: C₂₂H₂₅N₅O₃
• 分子量: 407.472
• InChiKey: FLDDGJZSDJUSHN-AZUAARDMSA-N

反应信息

• 作为产物：
  描述：

  在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以30 mg的产率得到2-((6S,9aR)-1-(2-aminophenyl)-6-benzyl-4,7-dioxohexahydro-1H-pyrazino[1,2-a]pyrimidin-8(2H)-yl)acetamide
  参考文献：
  名称：

  Regioselective Incorporation of Backbone Constraints Compatible with Traditional Solid-Phase Peptide Synthesis

  摘要：

  A protected aldehyde was attached via a two-carbon spacer to a peptide backbone amide nitrogen during a traditional Merrifield solid-phase synthesis. Acid-mediated unmasking of the aldehyde triggered the regioselective formation of cyclic N-acyliminiums between the aldehyde and the neighboring peptide amide nitrogen. In the absence of an internal nucleophile, the cyclic iminiums formed dihydropyrazinones, a six-membered peptide backbone constraint between two peptide amides. In the presence of an internal nucleophile, tetrahydropyrazinopyrimidinediones or tetrahydroimidazopyrazinediones were formed via tandem N-acyliminium ion cyclization-nucleophilic addition. The outcome of this nucleophilic addition was dependent on the substituent on the nitrogen nucleophile.

  DOI：

  10.1021/co300125m