methyl 1-benzyl-4,6-dioxo-3-(pyridin-2-yl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylate

• 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: methyl 1-benzyl-4,6-dioxo-3-(pyridin-2-yl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (1S,3R,3aS,6aR)-3-benzyl-4,6-dioxo-1-pyridin-2-yl-1,2,3a,6a-tetrahydropyrrolo[3,4-c]pyrrole-3-carboxylate
• 化学式: C₂₀H₁₉N₃O₄
• 分子量: 365.389
• InChiKey: VLXKNUVTSJSMMS-AXHMDWHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  97.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  吡啶-2-甲醛 、 马来酰亚胺 、 DL-苯基丙氨酸甲酯盐酸盐 在 calcium(II) trifluoromethanesulfonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 8.0h， 以86%的产率得到methyl 1-benzyl-4,6-dioxo-3-(pyridin-2-yl)octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  A Diastereoselective Three-Component Coupling Approach to Highly Substituted Pyrrolidines

  摘要：

  Building on the observation that metal complexation facilitates azomethine ylide formation, we report that chelating aldehydes participate in metal-templated, one-pot reactions with unprotected amino acid esters and activated olefins to provide highly substituted pyrrolidines. The high yields, broad substrate scope, excellent diastereoselectivities, functional group tolerance, and incorporation of commercially available materials in this reaction simplifies access to medicinally relevant proline derivatives.

  DOI：

  10.1021/jo101304q

文献信息

• A Diastereoselective Three-Component Coupling Approach to Highly Substituted Pyrrolidines
  作者：Mani Raj Chaulagain、Zachary D. Aron

  DOI：10.1021/jo101304q

  日期：2010.12.3

  Building on the observation that metal complexation facilitates azomethine ylide formation, we report that chelating aldehydes participate in metal-templated, one-pot reactions with unprotected amino acid esters and activated olefins to provide highly substituted pyrrolidines. The high yields, broad substrate scope, excellent diastereoselectivities, functional group tolerance, and incorporation of commercially available materials in this reaction simplifies access to medicinally relevant proline derivatives.