ethyl 6,8-dioxo-4,7-diphenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylate | 113370-82-4

• 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: ethyl 6,8-dioxo-4,7-diphenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylate
• 英文别名: ethyl 4,6-dioxo-3,5-diphenyloctahydropyrrolo[3,4-c]pyrrole-1-carboxylate；ethyl (1R,3S,3aR,6aS)-4,6-dioxo-1,5-diphenyl-2,3,3a,6a-tetrahydro-1H-pyrrolo[3,4-c]pyrrole-3-carboxylate
• CAS: 113370-82-4
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: ZERWLHWTZQSNAX-MHORFTMASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6,8-dioxo-4,7-diphenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylate 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 以99%的产率得到ethyl 6,8-dioxo-4,7-diphenyl-3,7-diazabicyclo<3.3.0>oct-3-ene-2-carboxylate
  参考文献：
  名称：

  XY–ZH系统作为潜在的1,3偶极子。部分8.吡咯烷类和Δ 5个-pyrrolines从α氨基酸的亚胺和它们与环状dipolarophiles酯的反应（3,7-二氮杂双环[3.3.0]辛烯）。醛存在下α-氨基酸及其酯的外消旋作用机理

  摘要：

  α-氨基酸酯的亚胺与芳族，杂环和脂族醛一起，通过在甲苯中加热时发生质变，立体定向生成偶氮甲碱。甲亚胺叶立德进行环加成到Ñ苯基马来，马来酸酐，和p -naphthoquinone经由一个内切-过渡状态，得到外消旋的，非对映异构单，cycloadducts。α-氨基酸在热乙酸中经历类似的环加成而不脱羧。讨论了在醛存在下α-氨基酸及其酯的外消旋作用机理。吡咯烷cycloadducts（22）平滑地氧化成相应的Δ 5 -pyrrolines（33）通过二氯二氰基对苯醌。

  DOI：

  10.1039/p19870002285
• 作为产物：
  描述：

  苄胺 在 silver(I) acetate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.17h， 生成 ethyl 6,8-dioxo-4,7-diphenyl-3,7-diazabicyclo<3.3.0>octane-2-carboxylate
  参考文献：
  名称：

  从烯丙基胺和乙二醛中获得 Azomethine Ylides 的新入口：改变对氨基酯前体的依赖

  摘要：

  报道了衍生自烯丙胺和乙二醛前体的偶氮甲碱叶立德的第一个例子。伯烯丙胺和 α-芳基胺与乙醛酸酯或 α-芳基乙二醛缩合得到共轭偶氮甲碱叶立德，可进行简单的 [3 + 2] 环加成，提供 5-烯基吡咯烷环加合物，不能通过经典使用氨基酯作为叶立德前体。

  DOI：

  10.1021/ol5022614

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.
• Synthesis of new chiral ferrocenyl P,N-ligands with a benzoxazole ring and their application in Ag-catalyzed asymmetric [3+2] cycloaddition
  作者：Sheng Yan、Cheng Zhang、Ya-Hui Wang、Zhong Cao、Zhuo Zheng、Xiang-Ping Hu

  DOI：10.1016/j.tetlet.2013.05.003

  日期：2013.7

  New chiral ferrocenyl P,N-ligands with a benzoxazole ring as the N-donor group have been synthesized from 2-aminophenol through a three-step transformation and successfully employed in the Ag-catalyzed asymmetric [3+2] cycloaddition of azomethine ylides with electron-deficient alkenes. High diastereoselectivities, excellent enantioselectivities, and good yields have been achieved for a variety of substrates, demonstrating the potential of these new P,N-ligands in asymmetric catalysis. (C) 2013 Elsevier Ltd. All rights reserved.