(1R,3S,3aR,6aS)-methyl octahydro-3-(4-methoxyphenyl)-5-methyl-4,6-dioxopyrrolo[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: (1R,3S,3aR,6aS)-methyl octahydro-3-(4-methoxyphenyl)-5-methyl-4,6-dioxopyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (1R,3S,3aR,6aS)-3-(4-methoxyphenyl)-5-methyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate；methyl (1S,3R,3aS,6aR)-1-(4-methoxyphenyl)-5-methyl-4,6-dioxo-2,3,3a,6a-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-3-carboxylate
• 化学式: C₁₆H₁₈N₂O₅
• 分子量: 318.329
• InChiKey: ZEZMVPHAUKHCOT-YVECIDJPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 甘氨酸,N-[(4-甲氧苯基)亚甲基]-,甲基酯 在 (S)-TF-Biphamphos 、 silver(I) acetate 作用下， 以 二氯甲烷 为溶剂， 生成 (1R,3S,3aR,6aS)-methyl octahydro-3-(4-methoxyphenyl)-5-methyl-4,6-dioxopyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  Highly enantioselective 1,3-dipolar cycloaddition of azomethine ylides catalyzed by AgOAc/TF-BiphamPhos

  摘要：

  一种新型高效的 AgOAc/TF-BiphamPhos 催化体系在偶氮甲酰亚胺与 N-取代马来酰亚胺和其他缺电子烯的不对称 1,3-二极环加成反应中显示出优异的反应性、非对映/非对映选择性和结构范围。

  DOI：

  10.1039/b902556a

文献信息

• Recoverable (<i>R</i>)- and (<i>S</i>)-Binap−Ag(I) Complexes for the Enantioselective 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides
  作者：Carmen Nájera、M. de Gracia Retamosa、José M. Sansano

  DOI：10.1021/ol701577k

  日期：2007.9.1

  The first enantioselective 1,3-dipolar cycloaddition reaction of amino acid derived azomethine ylides and maleimides catalyzed by very stable and recyclable chiral (R)- or (S)-binap-AgClO(4) complexes is described. The reactions are performed at room temperature, in good yields, with high endo diastereoselectivity and enantioselectivity, the complex being recovered by simple filtration.

  描述了由非常稳定且可循环利用的手性（R）-或（S）-binap-AgClO（4）络合物催化的氨基酸衍生的偶氮甲碱和马来酰亚胺的第一个对映选择性1,3-偶极环加成反应。反应在室温下以高收率进行，具有高的内非对映选择性和对映选择性，可通过简单过滤回收复合物。
• Enantioselective synthesis of polysubstituted prolines by Binap-silver-catalyzed 1,3-dipolar cycloadditions
  作者：Carmen Nájera、M. de Gracia Retamosa、José M. Sansano、Abel de Cózar、Fernando P. Cossío

  DOI：10.1016/j.tetasy.2008.12.021

  日期：2008.12

  The enantioselective 1,3-dipolar cycloaddition reaction of stabilized azomethine ylides, generated from iminoesters, with maleimides was efficiently achieved by intermediacy of an equimolar mixture of chiral (R)- or (S)-Binap and AgClO4. The high stability of the titled catalytic metal-complex to light exposure and its insolubility in toluene made possible its recovery and reutilization in other new process. In order to get a better understanding of the behavior of these chiral catalysts, we have carried out DFT1 calculations demonstrating the experimentally observed high enantio- and endo-selectivity through a very asynchronous transition state. (C) 2009 Elsevier Ltd. All rights reserved.