1,3a,4,5,6,6a-hexahydro-1,3-dimethyl-4,6-dioxo-5-phenylpyrrolo[3,4-c]pyrrole-1-carboxylate methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 1,3a,4,5,6,6a-hexahydro-1,3-dimethyl-4,6-dioxo-5-phenylpyrrolo[3,4-c]pyrrole-1-carboxylate methyl ester
• 英文别名: methyl (3S,3aS,6aR)-1,3-dimethyl-4,6-dioxo-5-phenyl-3a,6a-dihydropyrrolo[3,4-c]pyrrole-3-carboxylate
• 化学式: C₁₆H₁₆N₂O₄
• 分子量: 300.314
• InChiKey: YSKWQGYWVQGEOT-OZVIIMIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-methyl-4-methyl-4H-oxazolin-5-one 在 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 50.0h， 生成 1,3a,4,5,6,6a-hexahydro-1,3-dimethyl-4,6-dioxo-5-phenylpyrrolo[3,4-c]pyrrole-1-carboxylate methyl ester
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted Δ-Pyrrolines:  exo-Selective 1,3-Dipolar Cycloaddition Reactions with Azlactones

  摘要：

  We report herein a silver(I)-catalyzed exo-selective synthesis of highly substituted Delta1-pyrroline scaffolds from amino acid-derived münchnones. Silver acetate successfully catalyzed the cycloaddition reaction of azlactones with alkenes, generating Delta1-pyrrolines in very good yields without isomerization to the Delta2-pyrrolines or decarboxylation.

  DOI：

  10.1021/ja046149i

文献信息

• Gold(I)-Catalyzed Diastereo- and Enantioselective 1,3-Dipolar Cycloaddition and Mannich Reactions of Azlactones
  作者：Asa D. Melhado、Giovanni W. Amarante、Z. Jane Wang、Marco Luparia、F. Dean Toste

  DOI：10.1021/ja1095045

  日期：2011.3.16

  reactions with electron-deficient alkenes and N-sulfonyl aldimines to give products of 1,3-dipolar cycloaddition and Mannich addition reactions, respectively. Both of these reactions proceed with good to excellent diastereo- and enantioselectivity using a single class of gold catalysts, namely C(2)-symmetric bis(phosphinegold(I) carboxylate) complexes. The development of the azlactone Mannich reaction to

  吖内酯参与与缺电子烯烃和N-磺酰醛亚胺的立体选择性反应，分别产生1,3-偶极环加成和曼尼希加成反应的产物。这两个反应均使用一类金催化剂，即 C(2)-对称双(膦金(I)羧酸酯)络合物，以良好至优异的非对映选择性和对映选择性进行。描述了二氢唑酮曼尼希反应的发展，以提供完全保护的抗 α,β-二氨基酸衍生物。研究了几种无环 1,2-二取代烯烃的 1,3-偶极环加成反应以及所得环加合物的化学性质，以探讨该反应的立体化学过程。报告了环加成反应和曼尼希反应的反应动力学和串联质谱研究。这些研究支持了一种机制，其中金络合物通过亲核试剂活化而不是更典型的亲电子反应组分的活化来催化加成反应。
• Stereoselective Synthesis of Highly Substituted Δ-Pyrrolines:  <i>exo</i>-Selective 1,3-Dipolar Cycloaddition Reactions with Azlactones
  作者：Satyamaheshwar Peddibhotla、Jetze J. Tepe

  DOI：10.1021/ja046149i

  日期：2004.10.1

  We report herein a silver(I)-catalyzed exo-selective synthesis of highly substituted Delta1-pyrroline scaffolds from amino acid-derived münchnones. Silver acetate successfully catalyzed the cycloaddition reaction of azlactones with alkenes, generating Delta1-pyrrolines in very good yields without isomerization to the Delta2-pyrrolines or decarboxylation.