methyl (1S,3R,3aS,6aR)-3-(4-methoxyphenyl)-5-methyl-4,6-dioxooctahydropyrrolo[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 (1S,3R,3aS,6aR)-3-(4-methoxyphenyl)-5-methyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (1R,3S,3aR,6aS)-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-RNJOBUHISA-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 silver hexafluoroantimonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以85%的产率得到methyl (1S,3R,3aS,6aR)-3-(4-methoxyphenyl)-5-methyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  BINAP-AgSbF6 与 BINAP-AgClO4 配合物作为偶氮甲碱叶立德和烯烃的对映选择性 1,3-偶极环加成的催化剂

  摘要：

  这项工作得到了西班牙教育部长 y Ciencia (MEC) DGES 的支持 (Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU, the Hispano-Brazilian project PHB2008-0037-PC and CNPq)-General瓦伦西亚纳 (PROMETEO/2009/039) 和阿利坎特大学。

  DOI：

  10.1055/s-0029-1219534

文献信息

• Facile Method for 1,3-Dipolar Cycloaddition Reaction of Azomethine Ylides: Highly Stereoselective Synthesis of Substituted Pyrrolidine Derivatives
  作者：Serkan Yavuz、Hamdi Özkan、Gülçin Tok、Ali Dişli

  DOI：10.1002/jhet.1540

  日期：2013.11

  The substituted pyrolidine derivatives with high stereoselectivity were obtained through cycloaddition reaction in the presence of a Lewis acid namely diethylzinc by solvent‐free grinding method.

  在路易斯酸即二乙基锌的存在下，通过无溶剂研磨法，通过环加成反应获得了具有高立体选择性的取代吡咯烷衍生物。
• Binap-Gold(I) versus Binap-Silver Trifluoroacetate Complexes as Catalysts in 1,3-Dipolar Cycloadditions of Azomethine Ylides
  作者：María Martín-Rodríguez、Carmen Nájera、José M. Sansano、Abel de Cózar、Fernando P. Cossío

  DOI：10.1002/chem.201101606

  日期：2011.12.9

  The 1,3‐dipolar cycloaddition between azomethine ylides and alkenes is efficiently catalysed by [(Sa)‐Binap‐Au(tfa)}2] (Binap=2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl; tfa=trifluoroacetyl). Maleimides, 1,2‐bis(phenylsulfonyl)ethylene, chalcone and nitrostyrene were suitable dipolarophiles even when using sterically hindered 1,3‐dipole precursors. The results obtained in these transformations improve

  [（S a）-Binap-Au（tfa）} 2 ]（Binap = 2,2'-双（二苯基膦基）-1,1'-联萘基； tfa =三氟乙酰基）。马来酰亚胺，1,2-双（苯磺酰基）乙烯，查尔酮和硝基苯乙烯是适合的双极性亲和剂，即使使用空间受阻的1,3-偶极前体也是如此。在这些转化中获得的结果改进了在[Binap–Ag（tfa）]催化的相同反应中获得的相似结果。此外，还进行了计算研究，以证明手性金（I）配合物表现出的高对映选择性以及在该转化过程中观察到的非线性效应。
• 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。
• Enantiomerically Enriched 1,2-P,N-Bidentate Ferrocenyl Ligands for 1,3-Dipolar Cycloaddition and Transfer Hydrogenation Reactions
  作者：Irina Utepova、Polina Serebrennikova、Marina Streltsova、Alexandra Musikhina、Tatiana Fedorchenko、Oleg Chupakhin、Andrey Antonchick

  DOI：10.3390/molecules23061311

  日期：——

  Novel complexes of 1,2-P,N-bidentate ferrocenyl ligands with AgOAc or with [RuCl2(PPh3)3] as catalysts have been studied in asymmetric synthesis. The catalytic activity of these systems have been studied in [3+2]-cycloaddition of azomethine ylides with olefins and the asymmetric transfer hydrogenation of ketones.

  在不对称合成中研究了 1,2-P,N-二茂铁配体与 AgOAc 或 [RuCl2(PPh3)3] 作为催化剂的新型配合物。这些体系的催化活性已在偶氮甲碱叶立德与烯烃的 [3+2]-环加成反应和酮的不对称转移加氢反应中进行了研究。
• 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.