Ethyl 2-(2-amino-2-oxoethyl)-3-oxo-2,5,6,7,8,9-hexahydropyrrolo[1,2-a]azepine-1-carboxylate | 1604038-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - Pyrroloazepines
• 英文名称: Ethyl 2-(2-amino-2-oxoethyl)-3-oxo-2,5,6,7,8,9-hexahydropyrrolo[1,2-a]azepine-1-carboxylate
• 英文别名: ethyl 2-(2-amino-2-oxoethyl)-3-oxo-2,5,6,7,8,9-hexahydropyrrolo[1,2-a]azepine-1-carboxylate
• CAS: 1604038-33-6
• 化学式: C₁₄H₂₀N₂O₄
• 分子量: 280.324
• InChiKey: GGIALROJUZHYBD-UHFFFAOYSA-N

物化性质

• 沸点：
  537.1±50.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  89.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  马来酰亚胺 、 2-氮杂环庚-2-亚基乙酸乙酯 以 乙腈 为溶剂， 反应 8.0h， 以99%的产率得到Ethyl 2-(2-amino-2-oxoethyl)-3-oxo-2,5,6,7,8,9-hexahydropyrrolo[1,2-a]azepine-1-carboxylate
  参考文献：
  名称：

  Formal aza-[3+3] versus aza-[3+2] cycloadditions of heterocyclic enaminones with maleic anhydride and maleimides: skeletally diverse synthesis of pyrrolizidinones, indolizidinones, and pyrroloazepinones

  摘要：

  The domino aza-annulation of cyclic enaminones with maleic anhydride and maleimides was investigated, and selectively one-step skeletally diverse synthesis of each alkaloid-like pyrrolizidinone, indolizidinone, and pyrrolo[1,2-a]azepinone was developed, switching between aza-[3+3] and aza-[3+2] modes of formal cycloaddition reactions. For the synthesis of pyrroloazepinones, seven-membered enaminone and maleic anhydride or maleimides are efficient, via the [3+2] mode. To access indolizidinones, five or six-membered enaminones are the choice, and both [3+2] and [3+3] modes were viable exclusively with maleic anhydride. Pyrrolizidinone can be selectively synthesized in good yield through the [3+2] mode, only with five-membered enaminone and N-(4-NO2Ph)maleimide, under catalysis by PTSA. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.10.071

文献信息

• Formal aza-[3+3] versus aza-[3+2] cycloadditions of heterocyclic enaminones with maleic anhydride and maleimides: skeletally diverse synthesis of pyrrolizidinones, indolizidinones, and pyrroloazepinones
  作者：Silvio Cunha、Airam Oliveira Santos、José Tiago Menezes Correia、José Ricardo Sabino

  DOI：10.1016/j.tet.2013.10.071

  日期：2014.5

  The domino aza-annulation of cyclic enaminones with maleic anhydride and maleimides was investigated, and selectively one-step skeletally diverse synthesis of each alkaloid-like pyrrolizidinone, indolizidinone, and pyrrolo[1,2-a]azepinone was developed, switching between aza-[3+3] and aza-[3+2] modes of formal cycloaddition reactions. For the synthesis of pyrroloazepinones, seven-membered enaminone and maleic anhydride or maleimides are efficient, via the [3+2] mode. To access indolizidinones, five or six-membered enaminones are the choice, and both [3+2] and [3+3] modes were viable exclusively with maleic anhydride. Pyrrolizidinone can be selectively synthesized in good yield through the [3+2] mode, only with five-membered enaminone and N-(4-NO2Ph)maleimide, under catalysis by PTSA. (C) 2013 Elsevier Ltd. All rights reserved.