ethyl 1‐(4‐chlorophenyl)‐2‐methyl‐4‐(p‐tolyl)‐1H-pyrrole‐3‐carboxylate | 146537-41-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1‐(4‐chlorophenyl)‐2‐methyl‐4‐(p‐tolyl)‐1H-pyrrole‐3‐carboxylate
• 英文别名: Ethyl 1-(4-chlorophenyl)-2-methyl-4-(4-methylphenyl)pyrrole-3-carboxylate
• CAS: 146537-41-9
• 化学式: C₂₁H₂₀ClNO₂
• 分子量: 353.848
• InChiKey: NJFDLRHRKCRHED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1‐(4‐chlorophenyl)‐2‐methyl‐4‐(p‐tolyl)‐1H-pyrrole‐3‐carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以70%的产率得到1-(4-Chloro-phenyl)-2-methyl-4-p-tolyl-1H-pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Research on antibacterial and antifungal agents. VIII. synthesis and antimicrobial activity of 1,4-diarylpyrroles

  摘要：

  The synthesis and the antimicrobial activity of 1,4-diarylpyrroles are reported. The obtained data in comparison with pyrrolnitrin show that many acid derivatives 4 exhibit a selective activity against some strains of Candida spp and poor activity against strains of Candida albicans. All ester derivatives 3 are inactive. The results obtained are discussed on the basis of structure-activity relationships.

  DOI：

  10.1016/0223-5234(92)90092-f
• 作为产物：
  描述：

  2-[(4-chlorophenyl)amino]-1-(4-methylphenyl)ethan-1-one 、 乙酰乙酸乙酯 在 p-chlorobenzenamine hydrobromide 、 zinc(II) chloride 作用下， 以 苯 为溶剂， 反应 20.0h， 以73%的产率得到ethyl 1‐(4‐chlorophenyl)‐2‐methyl‐4‐(p‐tolyl)‐1H-pyrrole‐3‐carboxylate
  参考文献：
  名称：

  Research on antibacterial and antifungal agents. VIII. synthesis and antimicrobial activity of 1,4-diarylpyrroles

  摘要：

  The synthesis and the antimicrobial activity of 1,4-diarylpyrroles are reported. The obtained data in comparison with pyrrolnitrin show that many acid derivatives 4 exhibit a selective activity against some strains of Candida spp and poor activity against strains of Candida albicans. All ester derivatives 3 are inactive. The results obtained are discussed on the basis of structure-activity relationships.

  DOI：

  10.1016/0223-5234(92)90092-f

文献信息

• An efficient and recyclable nanocatalyst for the green and rapid synthesis of biologically active polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazole derivatives
  作者：Myo Thwin、Boshra Mahmoudi、Olga A. Ivaschuk、Qahtan A. Yousif

  DOI：10.1039/c9ra02325a

  日期：——

  for the green and rapid synthesis of biologically active polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazoles derivatives using Cu@imine/Fe3O4 MNPs catalyst under solvent-free conditions is explained. This catalyst showed high reactivity for the synthesis of a set of different derivatives of polysubstituted pyrroles and 1,2,4,5-tetrasubstituted imidazole derivatives under appropriate reaction

  一种利用Cu@imine/Fe 3 O 4绿色快速合成生物活性多取代吡咯和1,2,4,5-四取代咪唑衍生物的有效工艺解释了无溶剂条件下的 MNPs 催化剂。该催化剂在适当的反应条件和较短的反应时间下，对合成一组不同的多取代吡咯衍生物和1,2,4,5-四取代咪唑衍生物表现出高反应性。此外，催化剂还被回收和重复使用六次，反应性和产率没有显着降低。与已报道的工艺相比，该方法始终表现出催化剂负载量低、反应时间短、产物易于分离纯化、收率高、催化剂的可回收性和可回收性高等优点。
• Copper Schiff base complex immobilized on silica-coated Fe₃ O₄ nanoparticles: a recoverable and efficient catalyst for synthesis of polysubstituted pyrroles
  作者：Seyedeh Aghigh Hamrahian、Jamshid Rakhtshah、Seyedeh Mohadeseh Mousavi Davijani、Sadegh Salehzadeh

  DOI：10.1002/aoc.4501

  日期：2018.10

  In this work, a copper Schiff base complex immobilized on silica‐coated Fe3O4 nanoparticles is synthesized, and studied as a highly efficient, recyclable, green and heterogeneous catalyst for the preparation of polysubstituted pyrroles under solvent‐free and mild conditions. This new catalyst was characterized by different techniques, such as Fourier transform infrared (FT‐IR), X‐ray powder diffraction

  在这项工作中，固定在二氧化硅涂层的Fe 3 O 4上的铜席夫碱络合物纳米颗粒已被合成，并作为一种高效，可回收，绿色和非均相的催化剂进行研究，用于在无溶剂和温和条件下制备多取代吡咯。这种新催化剂的特征在于不同的技术，例如傅立叶变换红外（FT-IR），X射线粉末衍射（XRD），场发射扫描电子显微镜（SEM），能量色散X射线光谱法（EDX），电感耦合等离子体（ICP）和振动样品磁力法（VSM）。在上述催化剂存在下，硝基甲烷，芳基醛，1,3-二羰基化合物和胺的简单，环境单锅多组分缩合可在室温下提供标题化合物。在最后，
• The solvent-free synthesis of polysubstituted pyrroles by a reusable copper Schiff base complex immobilized on silica coated Fe₃ O₄ , and DNA binding study of one resulting derivative as a potential anticancer drug
  作者：Jamshid Rakhtshah、Behrooz Shaabani、Sadegh Salehzadeh、Neda Hosseinpour Moghadam

  DOI：10.1002/aoc.4754

  日期：2019.3

  for the synthesis of polysubstituted pyrrole derivatives and the products were isolated with high turnover number (TON) and high to excellent yields. Among the new synthesized polysubstituted pyrrole derivatives, we explored the first computational and experimental binding study of methyl 1‐benzyl‐4‐(furan‐2‐yl)‐2‐methyl‐1H‐pyrrole‐3‐carboxylate (SP‐10) with calf thymus deoxyribonucleic acid (ct‐DNA)

  我们在本文中证明了固定在二氧化硅包覆的Fe 3 O 4上的新型铜席夫碱配合物的合成纳米粒子。使用傅立叶变换红外（FT-IR），X射线粉末衍射（XRD），振动样品磁强度法（VSM），扫描电子显微镜（SEM），能量色散X射线（EDX）分析了这种磁性纳米催化剂的结构和组成）和电感耦合等离子体原子发射光谱（ICP-AES）。发现该纳米复合材料是用于合成多取代的吡咯衍生物的有效纳米催化剂，并且以高周转数（TON）和高至优异的产率分离了产物。在新合成的多取代吡咯衍生物中，我们探索了第一甲基与苄基-4-（呋喃-2-基）-2-甲基-1H-吡咯-3-羧酸甲酯（SP-10）的计算和实验结合研究。小牛胸腺脱氧核糖核酸（ct‐DNA），建议将其作为潜在的抗癌活性。此外，通过分子对接技术验证了SP-10与DNA和人血清白蛋白（HSA）的结合方式。
• Research on antibacterial and antifungal agents. VIII. synthesis and antimicrobial activity of 1,4-diarylpyrroles
  作者：GC Porretta、M Biava、R Fioravanti、M Fischetti、C Melino、F Venza、P Bolle、B Tita

  DOI：10.1016/0223-5234(92)90092-f

  日期：1992.10

  The synthesis and the antimicrobial activity of 1,4-diarylpyrroles are reported. The obtained data in comparison with pyrrolnitrin show that many acid derivatives 4 exhibit a selective activity against some strains of Candida spp and poor activity against strains of Candida albicans. All ester derivatives 3 are inactive. The results obtained are discussed on the basis of structure-activity relationships.