3-(dimethylamino)-1-phenyl-1H-pyrrole-2,5-dione | 1621006-06-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 3-(dimethylamino)-1-phenyl-1H-pyrrole-2,5-dione
• 英文别名: 3-(Dimethylamino)-1-phenylpyrrole-2,5-dione
• CAS: 1621006-06-1
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: WIPZEHIWTHKJOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(dimethylamino)-1-phenyl-1H-pyrrole-2,5-dione 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 N'-{(E)-[4-(dimethylamino)-2,5-dioxo-1-phenyl-2,5-dihydro-1H-pyrrol-3-yl]methylidene}-4-methylbenzene-1-sulfonohydrazide
  参考文献：
  名称：

  Novel Schiff bases derived from N-aryl maleimide derivatives as an effective antimicrobial agent: Theoretical and experimental approach

  摘要：

  A set of new Schiff bases of N-aryl 3- and 4-substituted maleimides has been prepared via condensation of N-aryl 3- and 4- substituted maleimides with p-toluene sulfonyl hydrazide in acidic medium at room temperature. The structures of synthesized compounds were characterized by IR, H-1 NMR, C-13 NMR, MS spectral data, and further confirmed by single-crystal x-ray crystallography for 5c. The computational study was carried out using Gaussian 09 software by using the B3LYP/6-311 + G(d,p) basis set. Single-crystal study results showed much closeness with computational study results. These novel compounds were screened for their antimicrobial activity against two pathogenic bacteria such as Escherichia coli (ATCC8739) and Staphylococcus aureus (ATCC25923) and two pathogenic fungi such as Aspergillus niger (MCIM10231) and Candida albicans (MTCC6275). The investigation of antimicrobial screening data showed that the most of tested compounds are moderate to good microbial inhibitors.

  DOI：

  10.1016/j.bioorg.2020.104129
• 作为产物：
  描述：

  N-苯丁二醯亞胺 在 溴 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-(dimethylamino)-1-phenyl-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Patil, Nilesh S.; Deshmukh, Ganesh B.; Mahale, Keshao A., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2015, vol. 54B, # 2, p. 272 - 278

  摘要：

  DOI：

文献信息

• Cu/Ag-Cocatalyzed Aerobic Oxidative Amination and CuCl₂-Mediated Aerobic Oxidative Chloroamination of Maleimides
  作者：Yu-Long An、He-Hui Zhang、Zhen-Hua Yang、Long Lin、Sheng-Yin Zhao

  DOI：10.1002/ejoc.201600923

  日期：2016.11

  An efficient Cu(OAc)2/Ag2CO3-cocatalyzed approach for the synthesis of 3-aminomaleimides and 3-amino-4-indolylmaleimides has been developed with satisfactory yields. A series of primary and secondary amines are compatible with this reaction. In addition, treatment of maleimides with primary amines using 1 equiv. of CuCl2 leads to the formation of chloroamination products such as 3-amino-4-chloromaleimides

  已开发出一种有效的 Cu(OAc)2/Ag2CO3 共催化方法来合成 3-氨基马来酰亚胺和 3-氨基-4-吲哚基马来酰亚胺，收率令人满意。一系列伯胺和仲胺与该反应相容。此外，使用 1 当量的伯胺处理马来酰亚胺。CuCl2 通过自由基型机制导致氯胺化产物如 3-氨基-4-氯马来酰亚胺的形成。
• 一种3-氨基-N-取代的马来酰亚胺类化合物 的制备方法
  申请人：东华大学

  公开号：CN105949106B

  公开（公告）日：2018-08-03

  本发明涉及一种3‑氨基‑N‑取代的马来酰亚胺类化合物的制备方法，其特征在于：所述化合物的结构式为：其中，R1为苯基或苄基，NR2R3为吡咯烷基、吗啉基、苄胺基或二甲胺基。制备：将N‑取代的马来酰亚胺、胺类化合物、催化剂加入溶剂中，加热至25℃～140℃反应1～12小时，提纯，即得。本发明制备的3‑氨基‑N‑取代的马来酰亚胺类化合物反应操作简单，收率较高，反应路线短，产生三废少，易于工业化生产。
• Copper-catalyzed direct oxidative amination of maleimides and quinones with formamides in the presence of an oxidant KIO3
  作者：Yu Dong、Zhen-Zhen Peng、Lin Chen、Yue-Qin Lin、Mei-Feng Lan、Chun-Mei Wu、Zhi-Chuan Shi、Guowei Deng、Bing He

  DOI：10.1016/j.tet.2024.133916

  日期：2024.4

  A facile, efficient, and practical method for copper-catalyzed direct amination of maleimides and quinones with formamides in the presence of an oxidant KIO has been developed. It allows a facile access to a wide range of functionalized molecules with privileged scaffolds in drugs and natural products such as maleimides and quinones. A variety of substituted 3-amino-maleimides and 2-amino-quinones

  开发了一种在氧化剂 KIO 存在下铜催化马来酰亚胺和醌与甲酰胺直接胺化的简便、高效且实用的方法。它可以轻松获得各种功能化分子，并在药物和天然产物（如马来酰亚胺和醌）中具有特殊的支架。合成了多种取代的3-氨基马来酰亚胺和2-氨基醌，产率中等至优异。
• Synthesis and biological evaluation of novel N-aryl maleimide derivatives clubbed with α-hydroxyphosphonates
  作者：Nilesh S. Patil、Ganesh B. Deshmukh、Sambhaji V. Patil、Avinash D. Bholay、Nitin D. Gaikwad

  DOI：10.1016/j.ejmech.2014.06.053

  日期：2014.8

  A series of novel molecules 5a-g containing N-aryl maleimide and α-hydroxyphosphonate moieties were synthesized. A distinct approach for high-yielding synthesis of α-hydroxyphosphonates has been discovered using various catalyst and solvents. The structures of the synthesized compounds were elucidated by IR, NMR, MS and CHN analysis. All the synthesized compounds were tested for qualitative (Zone of inhibition) and quantitative (MIC) antimicrobial activities against two pathogenic bacteria such as Bacillus subtilis (NCIM 2250) and Escherichia coli (ATCC 25922) and four pathogenic fungi such as Candida albicans (MTCC 277), Candida tropicalis (MTCC184), Aspergillus niger (MCIM 545) and Aspergillus clavatus (MTCC 132). The investigation of antimicrobial screening data revealed that most of the tested compounds are moderate to good microbial inhibitors.