methyl (1S,3R,3aS,6aR)-5-methyl-4,6-dioxo-3-o-tolyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 1140972-14-0

• 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)-5-methyl-4,6-dioxo-3-o-tolyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl (1R,3S,3aR,6aS)-5-methyl-1-(2-methylphenyl)-4,6-dioxo-2,3,3a,6a-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-3-carboxylate
• CAS: 1140972-14-0
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: CGOWJTYBIFYYIV-RNJOBUHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-甲基马来酰亚胺 、 N-(2-methylbenzylidene)-glycine methyl ester 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)-5-methyl-4,6-dioxo-3-o-tolyloctahydropyrrolo[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。
• Binap-silver salts as chiral catalysts for the enantioselective 1,3-dipolar cycloaddition of azomethine ylides and alkenes
  作者：Juan Mancebo-Aracil、María Martín-Rodríguez、Carmen Nájera、José M. Sansano、Paulo R.R. Costa、Evanoel Crizanto de Lima、Ayres G. Dias

  DOI：10.1016/j.tetasy.2012.10.015

  日期：2012.12

  Binap-AgSbF6 catalyzed 1,3-dipolar cycloadditions between azomethine ylides and electrophilic alkenes are described and compared with analogous transformations mediated by other Binap-silver(I) salt complexes. Maleimides and 1,2-bis(phenylsulfonyl)ethylene are suitable dipolarophiles for obtaining very good enantioselectivities, even better values are generated by a multicomponent version. There are

  描述了Binap-AgSbF 6催化的甲亚胺烷基化物和亲电子烯烃之间的1,3-偶极环加成反应，并将其与其他Binap-银（I）盐配合物介导的类似转化进行了比较。马来酰亚胺和1，2-双（苯磺酰基）乙烯是获得非常好的对映选择性的合适的双亲亲油性，甚至通过多组分形式产生更好的对映选择性。二磺酰化的环加合物在顺式2,5-二取代的吡咯烷，天然产物的前体或抗病毒化合物的合成中有价值的中间体的总合成中有一些非常有趣的应用。
• 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.
• Binap-gold(I) trifluoroacetate as a bifunctional catalyst for the synthesis of chiral prolines through 1,3-dipolar cycloaddition of azomethine ylides
  作者：María Martín-Rodríguez、Carmen Nájera、José M. Sansano、Feng-Liu Wu

  DOI：10.1016/j.tetasy.2010.06.011

  日期：2010.5

  Highly enantioselective 1,3-dipolar cycloadditions of amino acid-derived azomethine ylides with alkenes have been performed, for the first time, under gold-catalysis using (S-a)- or (R-a)-Binap-gold(I) trifluoroacetate complexes, with the cationic Binap-gold acting as a Lewis acid and the counteranion as a base. Maleimides and trans-1,2-bis(phenylsulfonyl)ethylene were reacted with imino esters at room temperature in the absence of a base to afford, in very good yields, the corresponding polysubstituted prolines with total endo-diastereoselection and higher enantioselectivities than the Binap-silver trifluoroacetate complex. (C) 2010 Elsevier Ltd. All rights reserved.