ethyl (3aR,4S,6aS)-4-(4-nitrophenyl)-1,3-dioxo-2-phenyl-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole-5-carboxylate | 1386412-94-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: ethyl (3aR,4S,6aS)-4-(4-nitrophenyl)-1,3-dioxo-2-phenyl-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole-5-carboxylate
• 英文别名: (3aR,4S,6aS)-ethyl 4-(4-nitrophenyl)-1,3-dioxo-2-phenyl-1,2,3,3a,4,6a-hexahydro-cyclopenta[c]pyrrole-5-carboxylate；ethyl (3aR,4S,6aS)-4-(4-nitrophenyl)-1,3-dioxo-2-phenyl-4,6a-dihydro-3aH-cyclopenta[c]pyrrole-5-carboxylate
• CAS: 1386412-94-7
• 化学式: C₂₂H₁₈N₂O₆
• 分子量: 406.395
• InChiKey: PBAROJROFQGXBX-WDSOQIARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(p-nitrophenyl)-2-ethoxycarbonylallyl tert-butyl carbonate 、 N-苯基马来酰亚胺 在 (S)-1-benzhydryl-3-(1-(diphenylphosphino)-3-phenylpropan-2-yl)thiourea 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到ethyl (3aR,4S,6aS)-4-(4-nitrophenyl)-1,3-dioxo-2-phenyl-1,2,3,3a,4,6a-hexahydrocyclopenta[c]pyrrole-5-carboxylate
  参考文献：
  名称：

  手性多功能硫脲-膦催化 Morita-Baylis-Hillman 碳酸盐与马来酰亚胺的不对称 [3 + 2] 环化。

  摘要：

  我们开发了一种多功能硫脲 - 膦催化的 Morita-Baylis-Hillman (MBH) 碳酸酯与马来酰亚胺的不对称 [3 + 2] 环化，它可以有效地构建带有三个连续立体中心的官能化环戊烯，收率中等至极好，非对映选择性和对映选择性也很好. 在控制实验和以前的文献的基础上，还提出了一种合理的机制。

  DOI：

  10.3762/bjoc.8.121

文献信息

• Asymmetric [3+2] Cycloaddition of Olefins with Morita–Baylis–Hillman Carbonates Catalyzed by BINOL-Based Bifunctional Phosphine
  作者：Hai-Lei Cui、Xue Tang、Meng-Fan Li、Xing-Jie Xu、Yin Shi

  DOI：10.1055/s-0037-1611752

  日期：2019.4

  series of novel BINOL-based phosphines. These bifunctional organocatalysts can be used in the [3+2] cycloaddition of electron-deficient olefins and Morita–Baylis–Hillman (MBH) carbonates. Moderate to excellent yields (up to >99%) and good to excellent enantioselectivities (up to 95% ee) can be obtained in the cycloaddition reaction of maleimides and MBH carbonates. The application of these novel phosphines

  我们开发了一系列新型的基于 BINOL 的膦。这些双功能有机催化剂可用于缺电子烯烃和 Morita-Baylis-Hillman (MBH) 碳酸酯的 [3+2] 环加成。在马来酰亚胺和 MBH 碳酸酯的环加成反应中可以获得中等至优异的产率（高达 >99%）和良好至优异的对映选择性（高达 95% ee）。这些新型膦的应用可以进一步扩展到手性螺环吲哚的不对称合成（高达 85% ee）。本研究的结果表明 BINOL 部分在立体控制中起着重要作用。
• Asymmetric Construction of Functionalized Bicyclic Imides via [3 + 2] Annulation of MBH Carbonates Catalyzed by Dipeptide-Based Phosphines
  作者：Fangrui Zhong、Guo-Ying Chen、Xiaoyu Han、Weijun Yao、Yixin Lu

  DOI：10.1021/ol301647g

  日期：2012.7.20

  A highly enantioselective [3 + 2] annulation of MBH carbonates and maleimides catalyzed by chiral phosphines has been developed. In the presence of 5 mol % of L-Thr-L-Val-derived phosphine 6, functionalized bicyclic imides were prepared in excellent yields, and with high diastereoselectivities and nearly perfect enantioselectivities.
• Asymmetric [3+2]-Cycloaddition of Morita–Baylis–Hillman Carbonates with Maleimides Catalyzed by Chiral Ferrocenylphosphines
  作者：Aiping Tu、Haiwen Hu、Tieqi Du、Weihui Zhong

  DOI：10.1080/00397911.2014.943346

  日期：2014.12.2

  New chiral ferrocenylphosphines LB1-LB9 were designed and prepared through simple synthetic approaches. These air-stable ferrocenylphosphines were applied to promote asymmetric [3+2]-cycloaddition of Morita-Baylis-Hillman carbonates with maleimides, among which LB7 was shown to have good catalytic activity to afford the corresponding multifunctional cyclopentenes in up to 59% yield and up to 53% ee under mild reaction conditions. A plausible reaction mechanism was proposed.