2-(4-Methylphenoxy)-3-phenylsulfanyl-naphthalene-1,4-dione | 1235999-69-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(4-Methylphenoxy)-3-phenylsulfanyl-naphthalene-1,4-dione
• 英文别名: 2-(4-methylphenoxy)-3-phenylsulfanylnaphthalene-1,4-dione
• CAS: 1235999-69-5
• 化学式: C₂₃H₁₆O₃S
• 分子量: 372.444
• InChiKey: IAKRBGZFQVLMFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,3-二氯-1,4-萘醌 在 Ariel laundry detergent 、 Triton X-100 作用下， 以 水 为溶剂， 反应 1.08h， 生成 2-(4-Methylphenoxy)-3-phenylsulfanyl-naphthalene-1,4-dione
  参考文献：
  名称：

  Micelles catalyzed chemoselective synthesis ‘in water’ and biological evaluation of oxygen containing hetero-1,4-naphthoquinones as potential antifungal agents

  摘要：

  Various oxygen containing 1,4-naphthoquinone derivatives have been synthesized chemoselectively by an economical, viable green methodology approach using water as solvent with or without surfactants such as Triton X-100, SDS, LD (laundry detergent), and TBAB, a phase transfer catalyst and evaluated for their in vitro antifungal and antibacterial activity. The antifungal profile of 3, 4a, 4b, and 6 indicated that compounds 3a, 3b, 4b, 6a, and 6c have potent antifungal activity compared to clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Sporothrix schenckii, Trichophyton mentagraphytes, and Candida parapsilosis and compound 3b has been found to be a lead antifungal agent for further study. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.095

文献信息

• Water-promoted unprecedented chemoselective nucleophilic substitution reactions of 1,4-quinones with oxygen nucleophiles in aqueous micelles
  作者：Vishnu K. Tandon、Hardesh K. Maurya

  DOI：10.1016/j.tetlet.2010.05.071

  日期：2010.7

  Unique nucleophilic substitution and addition reactions of nitrogen and sulfur nucleophiles with 1,4-quinones in aqueous suspension with amines and thiols have recently been demonstrated by us.2 However, the reactivity of oxygen nucleophiles toward nucleophilic substitution compared to nitrogen and sulfur nucleophiles ‘on water’ is not facile. An unprecedented economical, green methodology approach

  最近我们已经证明了氮和硫亲核体与1，4-醌在胺和硫醇的水悬浮液中的独特亲核取代和加成反应。2然而，与“在水上”的氮和硫亲核试剂相比，氧亲核试剂对亲核取代的反应性并不容易。已经证明了一种空前的经济，绿色方法学方法，该方法使用普通洗衣粉（LD；洗衣粉，0.5 mol％，可重复使用）/ SDS作为表面活性剂“在水中”，以优异的产率被1,4-醌中的氧亲核试剂亲核取代。
• Micelles catalyzed chemoselective synthesis ‘in water’ and biological evaluation of oxygen containing hetero-1,4-naphthoquinones as potential antifungal agents
  作者：Vishnu K. Tandon、Hardesh K. Maurya、Nripendra N. Mishra、Praveen K. Shukla

  DOI：10.1016/j.bmcl.2011.08.095

  日期：2011.11

  Various oxygen containing 1,4-naphthoquinone derivatives have been synthesized chemoselectively by an economical, viable green methodology approach using water as solvent with or without surfactants such as Triton X-100, SDS, LD (laundry detergent), and TBAB, a phase transfer catalyst and evaluated for their in vitro antifungal and antibacterial activity. The antifungal profile of 3, 4a, 4b, and 6 indicated that compounds 3a, 3b, 4b, 6a, and 6c have potent antifungal activity compared to clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Sporothrix schenckii, Trichophyton mentagraphytes, and Candida parapsilosis and compound 3b has been found to be a lead antifungal agent for further study. (C) 2011 Elsevier Ltd. All rights reserved.