2,5-bis(pyrrolidino)-3,6-dichloro-1,4-benzoquinone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-bis(pyrrolidino)-3,6-dichloro-1,4-benzoquinone
• 英文别名: 2,5-Dichloro-3,6-dipyrrolidin-1-ylbenzo-1,4-quinone；2,5-dichloro-3,6-dipyrrolidin-1-ylcyclohexa-2,5-diene-1,4-dione
• 化学式: C₁₄H₁₆Cl₂N₂O₂
• mdl: MFCD03547520
• 分子量: 315.199
• InChiKey: POJAIHQUHFGYFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  四氢吡咯 、 四氯苯醌 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 6.03h， 以81%的产率得到2,5-bis(pyrrolidino)-3,6-dichloro-1,4-benzoquinone
  参考文献：
  名称：

  Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones “In-Water” and their biological evaluation as antibacterial and antifungal agents

  摘要：

  Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio) cyclohexa-2,5-diene-1,4-diones (4d-14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa-2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst "In-Water" by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.022

文献信息

• Cine-substitution in reactions of dichloro-1,4-benzoquinones with pyrrolidine
  作者：S. V. Chapyshev、T. Ibata

  DOI：10.1007/bf01431116

  日期：1996.11

  Products ofcine-substitution are formed in reactions of 2,5- and 2,6-dichloro-1,4-benzoquinones with pyrrolidine. The main reason for amination of chloroquinones by pyrrolidinevia the mechanism ofcine-substitution is the high basicity of this amine. A high degree of localization of the π-bond in the molecules of the starting chloroquinones and the strong conjugation of the amino group with the quinone

  在 2,5- 和 2,6-二氯-1,4-苯醌与吡咯烷的反应中会形成电影取代的产物。吡咯烷通过电影取代机制将氯醌胺化的主要原因是该胺的高碱性。起始氯醌分子中 π 键的高度定位以及中间体单氨基醌分子中氨基与醌环的强共轭是另外两个有利于提高电影产率的因素-代换。
• Micelles catalyzed chemo- and regio-selective one pot and one step synthesis of 2,3,5,6-tetrakis(alkyl and arylsulfanyl)-1,4-benzoquinones and 2,5-diaminosubstituted-1,4-benzoquinones “In-Water” and their biological evaluation as antibacterial and antifungal agents
  作者：Vishnu K. Tandon、Sandeep Kumar、Nripendra N. Mishra、Praveen K. Shukla

  DOI：10.1016/j.ejmech.2012.07.022

  日期：2012.10

  Chemo- and regio-selective one pot and one step synthesis of novel 2,3,5,6-tetrakis (substituted thio) cyclohexa-2,5-diene-1,4-diones (4d-14), 2,5-dichloro-3,6-diaminocyclohexa-2,5-diene-1,4-diones and 2,5-diaminocyclohexa-2,5-diene-1,4-diones (16) by economical green methodology approach using LD (Laundry detergent) as a catalyst "In-Water" by nucleophilic addition and substitution reactions of 1,4-benzoquinone and chloranil with sulfur and nitrogen nucleophiles in high yields has been demonstrated. The antifungal profile of 4 and 16 indicates that compounds 4d and 16f had better antifungal activity compared to clinically prevalent antifungal drugs Fluconazole, 5-Fluorocytosine and Clotrimazole against Sporothrix schenckii and Trichophyton mentagraphytes. 16f had also been found to possess better antibacterial activity compared to Ampicillin in vitro against Escherichia coli, Staphylococcus aureus and Klebsiella pneumoniae. Compound 16f did not exhibit any toxicity towards mammalian cells L929. (C) 2012 Elsevier Masson SAS. All rights reserved.

表征谱图