3-((4-methylbenzyl)amino)-1-phenylpyrrolidine-2,5-dione | 827314-21-6

• 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: 3-((4-methylbenzyl)amino)-1-phenylpyrrolidine-2,5-dione
• 英文别名: 3-{[(4-Methylphenyl)methyl]amino}-1-phenylpyrrolidine-2,5-dione；3-[(4-methylphenyl)methylamino]-1-phenylpyrrolidine-2,5-dione
• CAS: 827314-21-6
• 化学式: C₁₈H₁₈N₂O₂
• 分子量: 294.353
• InChiKey: MBTOABWWJINUDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-苯基马来酰亚胺 、 4-甲基苄胺 在 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以86%的产率得到3-((4-methylbenzyl)amino)-1-phenylpyrrolidine-2,5-dione
  参考文献：
  名称：

  通过协同催化将胺加成至马来酰亚胺

  摘要：

  包含路易斯酸锂酸和胺碱的协同体系显着提高了多种胺与马来酰亚胺的共轭加成速率。这种操作简单，可扩展的方法可提供高收率和纯度的单加成产物。这种缀合已成功地以化学选择性连接方式应用于激酶抑制剂crizotinib，以创建新型荧光探针。

  DOI：

  10.1002/adsc.201800160

文献信息

• Catalysts and methods for enantioselective conjugate additions of amines to unsaturated electrophiles
  申请人：Northwestern University

  公开号：US10781172B2

  公开（公告）日：2020-09-22

  Disclosed are complexes and methods of using the complexes as catalysts for addition of amines to unsaturated electrophiles, as well as novel compounds produced by the disclosed complexes and methods. The disclosed methods may utilize the disclosed complexes as catalysts for adding unprotected primary amines and secondary amines to unsaturated electrophiles in an enantioselective manner to produce novel compounds which may include amino substituted succinimide compounds.

  所公开的是络合物和使用络合物作为催化剂将胺加到不饱和亲电体上的方法，以及用所公开的络合物和方法生产的新型化合物。所公开的方法可利用所公开的络合物作为催化剂，以对映选择性的方式将未保护的伯胺和仲胺添加到不饱和亲电体中，从而生产出新型化合物，其中可包括氨基取代的琥珀酰亚胺化合物。
• Chemoselective, accelerated and stereoselective aza-Michael addition of amines to N-phenylmaleimide by using TMEDA based receptors
  作者：Yuefeng Bi、Laëtitia Bailly、Francis Marsais、Vincent Levacher、Cyril Papamicaël、Georges Dupas

  DOI：10.1016/j.tetasy.2004.10.006

  日期：2004.11

  An aza-Michael addition between a maleimide and amines is described in which the presence of simple amine receptors (TMEDA or trans-TMCDA) promote the chemo selectivity of the reaction (respectively, 1,2- and 1,4-addition). Additionally, both receptors are able to accelerate the reaction. Stoichiometries of complexes between receptors and amines were determined by H-1 NMR dilution experiments while enantiomeric excesses were observed on 1,4-adducts by using (1R,2R)-TMCDA. (C) 2004 Elsevier Ltd. All rights reserved.
• CATALYSTS AND METHODS FOR ENANTIOSELECIVE CONJUGATE ADDITION OF AMINES TO UNSATURATED ELECTROPHILES
  申请人：Northwestern University

  公开号：US20210002221A1

  公开（公告）日：2021-01-07

  Disclosed are complexes and methods of using the complexes as catalysts for addition of amines to unsaturated electrophiles, as well as novel compounds produced by the disclosed complexes and methods. The disclosed methods may utilize the disclosed complexes as catalysts for adding unprotected primary amines and secondary amines to unsaturated electrophiles in an enantioselective manner to produce novel compounds which may include amino substituted succinimide compounds.
• Conjugate Additions of Amines to Maleimides via Cooperative Catalysis
  作者：Brice E. Uno、Kristine K. Deibler、Carlos Villa、Arjun Raghuraman、Karl A. Scheidt

  DOI：10.1002/adsc.201800160

  日期：2018.4.17

  A cooperative system comprising of a lithium Lewis acid and amine base significantly enhances the rate of the conjugate addition of a wide array of amines to maleimides. This operationally simple, scalable method provides mono‐addition products in high yields and purity. This conjugation was successfully applied to the kinase inhibitor crizotinib in a chemoselective ligation to create novel fluorescent

  包含路易斯酸锂酸和胺碱的协同体系显着提高了多种胺与马来酰亚胺的共轭加成速率。这种操作简单，可扩展的方法可提供高收率和纯度的单加成产物。这种缀合已成功地以化学选择性连接方式应用于激酶抑制剂crizotinib，以创建新型荧光探针。