2-(1-methoxycarbonyl-3-oxo-5,6,7,8-tetrahydro-2H-indolizin-2-yl)acetic acid | 1604038-29-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(1-methoxycarbonyl-3-oxo-5,6,7,8-tetrahydro-2H-indolizin-2-yl)acetic acid
• CAS: 1604038-29-0
• 化学式: C₁₂H₁₅NO₅
• 分子量: 253.255
• InChiKey: ZRVWIKKRQNHDGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  马来酸酐 、 methyl piperidine-2-ylideneacetate 以 乙腈 为溶剂， 反应 1.0h， 以88%的产率得到2-(1-methoxycarbonyl-3-oxo-5,6,7,8-tetrahydro-2H-indolizin-2-yl)acetic acid
  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.