2-Piperidino-N-(4-methylphenyl)-maleinimid | 53281-81-5

• 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: 2-Piperidino-N-(4-methylphenyl)-maleinimid
• 英文别名: 3-piperidin-1-yl-1-p-tolyl-pyrrole-2,5-dione；1-(4-Methylphenyl)-3-piperidin-1-ylpyrrole-2,5-dione
• CAS: 53281-81-5
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: PFLLRHAANNLKCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-Piperidino-N-(4-methylphenyl)-maleinimid 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-methyl-N'-{(E)-[4-(piperidin-1-yl)-1-(4-methylphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]methylidene}benzene-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：

  1-(4-甲基苯基)吡咯烷-2,5-二酮 在 溴 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 2-Piperidino-N-(4-methylphenyl)-maleinimid
  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

• Die schwefelung c-substituierter maleinimide
  作者：M. Augustin、M. Köhler、S. Kazandji

  DOI：10.1016/s0040-4020(01)91501-7

  日期：1984.1
• AUGUSTIN, M.;KOEHLER, M.;KAZANDJI, S., TETRAHEDRON, 1984, 40, N 18, 3499-3502
  作者：AUGUSTIN, M.、KOEHLER, M.、KAZANDJI, S.

  DOI：——

  日期：——
• 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
  作者：Patil, Nilesh S.、Deshmukh, Ganesh B.、Mahale, Keshao A.、Gosavi, Kirankumar S.、Patil, Sambhaji V.

  DOI：——

  日期：——
• Novel Schiff bases derived from N-aryl maleimide derivatives as an effective antimicrobial agent: Theoretical and experimental approach
  作者：Arun M. Bhagare、Jayraj S. Aher、Manoj R. Gaware、Dnyaneshwar D. Lokhande、Anant V. Kardel、Avinash D. Bholay、Akshay C. Dhayagude

  DOI：10.1016/j.bioorg.2020.104129

  日期：2020.10

  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.