N-tert-butyl-2-(1,4-dioxo-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-2-(naphthalene-1-yl)acetamide | 1404118-39-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-tert-butyl-2-(1,4-dioxo-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-2-(naphthalene-1-yl)acetamide
• 英文别名: N-tert-butyl-2-(1,4-dioxo-3H-pyrrolo[1,2-a]pyrazin-2-yl)-2-naphthalen-1-ylacetamide
• CAS: 1404118-39-3
• 化学式: C₂₃H₂₃N₃O₃
• 分子量: 389.454
• InChiKey: VNBALLBJBPSDAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  异氰酸叔丁酯 、 甘氨酸甲酯盐酸盐 、 1-萘甲醛 、 吡咯-2-羧酸 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 2.67h， 以80%的产率得到N-tert-butyl-2-(1,4-dioxo-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)-2-(naphthalene-1-yl)acetamide
  参考文献：
  名称：

  Access to Indole- And Pyrrole-Fused Diketopiperazines via Tandem Ugi-4CR/Intramolecular Cyclization and Its Regioselective Ring-Opening by Intermolecular Transamidation

  摘要：

  An efficient approach for the synthesis of indole- and pyrrole-fused diketopiperazines has been developed. This protocol involves the Ugi four-component reaction (U-4CR) followed by an intramolecular cyclization of the Ugi products at room temperature to afford the desired products in good to excellent yields. In addition, it is interesting to report the subsequent regioselective ring-opening of diketopiperazine unit occurring via an intermolecular transamidation reaction under mild condition, resulting in the formation of highly functionalized indole-2-carboxamides and pyrrole-2-carboxamides.

  DOI：

  10.1021/jo3018704

文献信息

• Access to Indole- And Pyrrole-Fused Diketopiperazines via Tandem Ugi-4CR/Intramolecular Cyclization and Its Regioselective Ring-Opening by Intermolecular Transamidation
  作者：Shashi Pandey、Shahnawaz Khan、Awantika Singh、Harsh M. Gauniyal、Brijesh Kumar、Prem M. S. Chauhan

  DOI：10.1021/jo3018704

  日期：2012.11.16

  An efficient approach for the synthesis of indole- and pyrrole-fused diketopiperazines has been developed. This protocol involves the Ugi four-component reaction (U-4CR) followed by an intramolecular cyclization of the Ugi products at room temperature to afford the desired products in good to excellent yields. In addition, it is interesting to report the subsequent regioselective ring-opening of diketopiperazine unit occurring via an intermolecular transamidation reaction under mild condition, resulting in the formation of highly functionalized indole-2-carboxamides and pyrrole-2-carboxamides.