1-(4-methoxybenzyl)-3-bromo-4-morpholino-1H-pyrrole-2,5-dione | 1283088-76-5

• 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: 1-(4-methoxybenzyl)-3-bromo-4-morpholino-1H-pyrrole-2,5-dione
• 英文别名: 3-bromo-1-(4-methoxybenzyl)-4-morpholino-maleimide；3-bromo-1-(4-methoxybenzyl)-4-morpholino-1H-pyrrole-2,5-dione；3-Bromo-1-[(4-methoxyphenyl)methyl]-4-morpholin-4-ylpyrrole-2,5-dione
• CAS: 1283088-76-5
• 化学式: C₁₆H₁₇BrN₂O₄
• 分子量: 381.226
• InChiKey: DEHKIFNFJUWCCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(4-methoxybenzyl)-3-bromo-4-morpholino-1H-pyrrole-2,5-dione 在 aluminum (III) chloride 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 caesium carbonate 、 苯甲醚 、 1,3,5,7-四甲基-6-苯基-2,4,8-三氧杂-6-磷酰金刚烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-(4-chlorophenyl)-4-morpholino-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Development of Methods for the Synthesis of Libraries of Substituted Maleimides and α,β-Unsaturated-γ-butyrolactams

  摘要：

  Synthetic methods for the preparation of maleimide and alpha,beta-unsaturated-gamma-butyrolactam compound collections are described. These routes take advantage of Pd cross-coupling and conjugate addition/elimination reactions to permit the facile production of bisaryl-maleimides, anilinoaryl-maleimides, and bisanilino-maleimides while allowing control over the synthesis of symmetrical or nonsymmetrical derivatives. Similarly, the chemistry developed allows for the generation of bisaryl substituted alpha,beta-unsaturated-gamma-butyrolactams. The scope and limitations of the approaches are presented.

  DOI：

  10.1021/jo1025805
• 作为产物：
  描述：

  吗啉 、 3,4-dibromo-2,5-dihydro-1-(4-methoxybenzyl)-1H-pyrrole-2,5-dione 在 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以98%的产率得到1-(4-methoxybenzyl)-3-bromo-4-morpholino-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Development of Methods for the Synthesis of Libraries of Substituted Maleimides and α,β-Unsaturated-γ-butyrolactams

  摘要：

  Synthetic methods for the preparation of maleimide and alpha,beta-unsaturated-gamma-butyrolactam compound collections are described. These routes take advantage of Pd cross-coupling and conjugate addition/elimination reactions to permit the facile production of bisaryl-maleimides, anilinoaryl-maleimides, and bisanilino-maleimides while allowing control over the synthesis of symmetrical or nonsymmetrical derivatives. Similarly, the chemistry developed allows for the generation of bisaryl substituted alpha,beta-unsaturated-gamma-butyrolactams. The scope and limitations of the approaches are presented.

  DOI：

  10.1021/jo1025805

文献信息

• Aminohalogenation of maleimides with alkylamines and XCH ₂ CH ₂ X (X = Cl, Br)
  作者：Jingjing Wang、Yaling Xu、Luya Chen、Yunfei Ma、Ge Wu

  DOI：10.1002/aoc.7046

  日期：2023.4

  nucleophilic substitution of organohalides with alkylamines is one of the most heralded reactions in synthetic chemistry. However, the resulting halide anions are often wasted in routine workup experiments and not fully utilized. Herein, we report a halogen recycling strategy for radical aminohalogenation of maleimides with XCH2CH2X (X = Cl, Br) and alkylamines with excellent functional group compatibility

  用烷基胺对有机卤化物进行亲核取代是合成化学中最受瞩目的反应之一。然而，由此产生的卤化物阴离子经常被浪费在常规后处理实验中，而没有得到充分利用。在此，我们报告了一种卤素回收策略，用于马来酰亚胺与 XCH 2 CH 2 X (X = Cl, Br) 和具有优异官能团相容性的烷基胺的自由基氨基卤化。38 种氨基卤化产物、双重氨基氯化和去甲替林的后期乙烯基氯化证明了该策略的出色通用性。
• Development of Methods for the Synthesis of Libraries of Substituted Maleimides and α,β-Unsaturated-γ-butyrolactams
  作者：Emelia Awuah、Alfredo Capretta

  DOI：10.1021/jo1025805

  日期：2011.5.6

  Synthetic methods for the preparation of maleimide and alpha,beta-unsaturated-gamma-butyrolactam compound collections are described. These routes take advantage of Pd cross-coupling and conjugate addition/elimination reactions to permit the facile production of bisaryl-maleimides, anilinoaryl-maleimides, and bisanilino-maleimides while allowing control over the synthesis of symmetrical or nonsymmetrical derivatives. Similarly, the chemistry developed allows for the generation of bisaryl substituted alpha,beta-unsaturated-gamma-butyrolactams. The scope and limitations of the approaches are presented.