2-n-octyl-2H-naphtho[2,3-d][1,2,3]triazole-4,9-dione | 1158909-53-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-n-octyl-2H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
• 英文别名: 2-Octylbenzo[f]benzotriazole-4,9-dione
• CAS: 1158909-53-5
• 化学式: C₁₈H₂₁N₃O₂
• 分子量: 311.384
• InChiKey: ICKGTMGUKLJPRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  64.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-溴辛烷 、 1,4-萘醌 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以52%的产率得到1-n-octyl-1H-naphtho[2,3-d][1,2,3]triazole-4,9-dione
  参考文献：
  名称：

  一锅合成1-和2-取代的萘并[2,3- d ] [1,2,3]三唑-4,9-二酮

  摘要：

  一锅三组分[2 + 3]环加成反应，用于合成1-烷基1 H-萘[2,3- d ] [1,2,3]三唑-4,9-二酮和2-烷基2已经开发了H-萘[2,3- d ] [1,2,3]三唑-4,9-二酮。通过利用碱性不同的优点，可以得到纯度高的两种产品。这两种产品独特的杂环支架可以发挥有趣的化学和生物学特性。合成方案简明扼要，适用于按比例放大所需产物的合成。

  DOI：

  10.1021/jo9004926

文献信息

• Library Synthesis and Antibacterial Investigation of Cationic Anthraquinone Analogs
  作者：Marina Y. Fosso、Ka Yee Chan、Rylee Gregory、Cheng-Wei Tom Chang

  DOI：10.1021/co2002075

  日期：2012.3.12

  We report the parallel synthesis of a series of novel 4,9-dioxo-4,9-dihydro-1H-naphtho[2-,3-d][1,2,3],triazol-3-ium chloride salts, which are analogs to cationic anthraquinones. Three synthetic protocols were examined leading to a convenient and facile library synthesis of the cationic anthraquinone analogs that contain double alkyl chains of various lengths (C-2-C-12) at N-1 and N-3 positions. The antibacterial activities of these compounds were evaluated against Gram positive bacterium Staphyloccous aureus and Gram negative bacterium Escherichia coli. The antibacterial activities of these compunds were expected to be associated with the structural features of naphthoquinenone, cation and lypophilic alkyl chain and, interestingly, they showed much higher levels of antibacterial activites against G+ than G- bacteria. In addtion, when the total number of carbon atoms of the alkyl groups at both N-1 and N-3 positions lies between 9 and 18, the bactericidal activity against S aureus increased with increasing alkyl chain length at both N-atoms with MIC <= 1 mu g/mL.