diethyl (1S,3R,3aS,6aR)-1,5-dibenzyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1,3-dicarboxylate

• 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: diethyl (1S,3R,3aS,6aR)-1,5-dibenzyl-4,6-dioxooctahydropyrrolo[3,4-c]pyrrole-1,3-dicarboxylate
• 英文别名: diethyl (1R,3S,3aR,6aS)-3,5-dibenzyl-4,6-dioxo-1,2,3a,6a-tetrahydropyrrolo[3,4-c]pyrrole-1,3-dicarboxylate
• 化学式: C₂₆H₂₈N₂O₆
• 分子量: 464.518
• InChiKey: IMOQFRKYLZFXHG-JJEXOMBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  乙醛酸乙酯 、 N-苄基马来酰亚胺 、 (2S)-2-氨基-3-苯丙酸乙酯 在 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 silver carbonate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以77%的产率得到
  参考文献：
  名称：

  Binap–silver-catalyzed enantioselective multicomponent 1,3-dipolar cycloaddition of azomethines ylides derived from ethyl glyoxylate

  摘要：

  The enantioselective binap-silver catalyzed multicomponent 1,3-dipolar cycloaddition using ethyl glyoxylate, phenylalanine ethyl ester, and maleimides is described. The employment of basic silver carbonate allows the reaction to take place in the absence of an extra base giving high yields and ee. In addition, low-level calculations regarding the importance of the benzyl substituent at the alpha-position of the amino ester justify the expected absolute configuration of the final cycloadducts and the observed high enantiodiscrimination. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2015.05.005

文献信息

• Binap–silver-catalyzed enantioselective multicomponent 1,3-dipolar cycloaddition of azomethines ylides derived from ethyl glyoxylate
  作者：Juan Mancebo-Aracil、Carmen Nájera、José M. Sansano

  DOI：10.1016/j.tetasy.2015.05.005

  日期：2015.7

  The enantioselective binap-silver catalyzed multicomponent 1,3-dipolar cycloaddition using ethyl glyoxylate, phenylalanine ethyl ester, and maleimides is described. The employment of basic silver carbonate allows the reaction to take place in the absence of an extra base giving high yields and ee. In addition, low-level calculations regarding the importance of the benzyl substituent at the alpha-position of the amino ester justify the expected absolute configuration of the final cycloadducts and the observed high enantiodiscrimination. (C) 2015 Elsevier Ltd. All rights reserved.