methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-bromophenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate | 939799-27-6

• 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)-4,6-dioxo-3-(p-bromophenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
• 英文别名: methyl 3-(4-bromophenyl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate；methyl (1S,3R,3aS,6aR)-3-(4-bromophenyl)-4,6-dioxo-5-phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate；methyl (1S,3R,3αS,6αR)-3-(4-bromophenyl)-4,6-dioxo-5phenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate；methyl (1R,3S,3aR,6aS)-1-(4-bromophenyl)-4,6-dioxo-5-phenyl-2,3,3a,6a-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-3-carboxylate
• CAS: 939799-27-6
• 化学式: C₂₀H₁₇BrN₂O₄
• 分子量: 429.27
• InChiKey: CFAQMIOLGBSBGW-YVSFHVDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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-苯基马来酰亚胺 、 methyl (E)-N-[(p-bromophenyl)methylene]glycinate 在 (S_Fc)-[2-(2-quinolinuinolin-2-yl)ferrocen-1-yl]diphenylphosphine 、 silver(I) acetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以64%的产率得到methyl (1S,3R,3aS,6aR)-4,6-dioxo-3-(p-bromophenyl)-5-phenyl-octahydropyrrolo[3,4-c]pyrrole-1-carboxylate
  参考文献：
  名称：

  用于 1,3-偶极环加成和转移氢化反应的对映体富集的 1,2-P,N-二茂二茂铁基配体

  摘要：

  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。

  DOI：

  10.3390/molecules23061311

文献信息

• N-tert-Butanesulfinyl imine and aromatic tertiary amide derived non-biaryl atropisomers as chiral ligands for silver-catalyzed endo-selective [3+2] cycloaddition of azomethine ylides with maleimides
  作者：Xing-Feng Bai、Jin Zhang、Chun-Gu Xia、Jian-Xing Xu、Li-Wen Xu

  DOI：10.1016/j.tet.2015.09.068

  日期：2016.5

  Simple modifications of our novel ligand (Xing-Phos) were presented in this work, and a series of aromatic tertiary amide derived non-biaryl atropisomers were successfully synthesized in good yields. In addition, it was found that the multifunctional aromatic tertiary amide derived non-biaryl atropisomers exhibited an excellent endo-selectivity in the silver-catalyzed [3+2]-cycloaddition of azomethine ylides with N-aromatic maleimide. And especially, good to high levels of enantioselectivity (up to 98% ee) was obtained with a wide range of substrates in the presence of syn-(R, R-S)-2a (Xing-Phos). Furthermore, on the basis of the experimental data, it was demonstrated that a trace amount of water play an important role in the enhancement of enantioselectivity. (C) 2015 Elsevier Ltd. All rights reserved.