1-benzyl-3-ethylmaleimide | 889101-84-2

• 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: 1-benzyl-3-ethylmaleimide
• 英文别名: 1-benzyl-3-ethyl-1H-pyrrole-2,5-dione；1-Benzyl-3-ethylpyrrole-2,5-dione
• CAS: 889101-84-2
• 化学式: C₁₃H₁₃NO₂
• 分子量: 215.252
• InChiKey: HLTGHSLWTYTESP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyl-3-ethylmaleimide 、 3-氯苯硼酸 在 氢氧化钾 、 bis(ethylene)rhodium(I) chloride dimer 、 C.I.酸性棕21 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 1-Benzyl-3-(3-chloro-phenyl)-4-ethyl-pyrrolidine-2,5-dione 、 (R)-1-Benzyl-3-(3-chloro-phenyl)-3-ethyl-pyrrolidine-2,5-dione
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Construction of Quaternary Carbon Stereocenters:  Ligand-Dependent Regiocontrol in the 1,4-Addition to Substituted Maleimides

  摘要：

  A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to substituted maleimides has been described. The regioselectivity in this reaction is controlled by the choice of ligand (dienes or bisphosphines), and 1,4-adducts with a quaternary stereocenter can be obtained with high regio- and enantioselectivity by the use of (R)-H8-binap.

  DOI：

  10.1021/ja061430d
• 作为产物：
  描述：

  2-Ethylbut-2-enedioic acid 在 溶剂黄146 、 三氟乙酸酐 作用下， 反应 35.0h， 生成 1-benzyl-3-ethylmaleimide
  参考文献：
  名称：

  使用手性菲咯啉-钯催化剂区域和对映选择性合成带有全碳四元中心的琥珀酰亚胺

  摘要：

  在 C3 位具有全碳四元立构中心的手性琥珀酰亚胺的合成很重要，但仍然具有挑战性。目前的工作展示了手性 1,10-菲咯啉-Pd 络合物 (L1-PdClL1-PdCl2催化的不对称共轭加成反应可以在克级上进行，并且也可用于将此类立体中心引入到生物活性分子。

  DOI：

  10.1002/adsc.202301486

文献信息

• Functional rearrangement of 3-Cl or 3,3-diCl-γ-lactams bearing a secondary 1-chloroalkyl substituent at C-4
  作者：Mariella Pattarozzi、Fabrizio Roncaglia、Luca Accorsi、Andrew F. Parsons、Franco Ghelfi

  DOI：10.1016/j.tet.2009.11.111

  日期：2010.2

  The study of the reaction with MeONa/MeOH of chlorinated gamma-lactams. prepared from the atom transfer radical cyclization of N-allyl-alpha-perchloroamides, has been extended to the case of substiates carrying an exo halogen atom on a branched carbon Only with secondary exo C-Cl groups, that are not located on a fused ring, does the functional rearrangement follow the typical transformation route, Which With trichloro-lactams can proceed further to give 4-alkylidene derivatives From a practical point of view, the outcome of the reaction with di- or trichloio N-cinnamylamides is synthetically valuable, affording the 5-methoxy-IH-pyrrol-2(5H)-one or 3-benzylidenepyrrlidine-2.5-dione. respectively. in good to excellent yield (C) 2009 Elsevier Ltd All rights reserved
• Rhodium-Catalyzed Asymmetric Construction of Quaternary Carbon Stereocenters:  Ligand-Dependent Regiocontrol in the 1,4-Addition to Substituted Maleimides
  作者：Ryo Shintani、Wei-Liang Duan、Tamio Hayashi

  DOI：10.1021/ja061430d

  日期：2006.5.1

  A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to substituted maleimides has been described. The regioselectivity in this reaction is controlled by the choice of ligand (dienes or bisphosphines), and 1,4-adducts with a quaternary stereocenter can be obtained with high regio- and enantioselectivity by the use of (R)-H8-binap.
• Regio‐ and Enantioselective Synthesis of Succinimides Bearing All‐Carbon Quaternary Centers Using a Chiral Phenanthroline‐Palladium Catalyst
  作者：Yudai Kuroiwa、Masafumi Tamura

  DOI：10.1002/adsc.202301486

  日期：——

  all‐carbon quaternary stereocenters at the C3 position is important, but remains challenging. The present work demonstrates conjugate additions with catalysis by a chiral 1,10‐phenanthroline‐Pd complex (L1‐PdCl2) that exhibit complete regioselectivity with a high degree of enantioselectivity. These reactions afford chiral 3,3‐disubstituted succinimides having all‐carbon quaternary stereocenters with 40%−99%

  在 C3 位具有全碳四元立构中心的手性琥珀酰亚胺的合成很重要，但仍然具有挑战性。目前的工作展示了手性 1,10-菲咯啉-Pd 络合物 (L1-PdClL1-PdCl2催化的不对称共轭加成反应可以在克级上进行，并且也可用于将此类立体中心引入到生物活性分子。