1-tetradecyl-4,4'-bipyridinium bromide | 1383253-38-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-tetradecyl-4,4'-bipyridinium bromide
• 英文别名: 1-tetradecyl-4,4'-dipyridinium bromide；4-Pyridin-4-yl-1-tetradecylpyridin-1-ium;bromide
• CAS: 1383253-38-0
• 化学式: Br*C₂₄H₃₇N₂
• 分子量: 433.475
• InChiKey: UYXVQDIWYDDFRV-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  16.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  溴乙烷 、 1-tetradecyl-4,4'-bipyridinium bromide 以 乙腈 为溶剂， 反应 0.5h， 以60%的产率得到1-tetradecyl-1'-ethyl-4,4'-bipyridinium dibromide
  参考文献：
  名称：

  The antibacterial activity of 4,4′-bipyridinium amphiphiles with conventional, bicephalic and gemini architectures

  摘要：

  Dialkyl 4,4'-bipyridinium compounds are widely employed for their useful redox properties, and are commonly known as viologens due to their intense coloration upon reduction. Despite their prevalence and amphiphilic nature, the antibacterial activity of these compounds remains largely unreported. We have thus prepared a series of mono-and bis-alkylated analogs of 4,4'-bipyridine to investigate structure-activity relationships in their inhibition of a battery of Gram positive and Gram negative bacteria. The prepared cationic compounds were conventional (one cationic head, one non-polar tail), bicephalic (two heads, one tail), or gemini (two heads, two tails) in their amphiphilic structure. Additionally, an isomeric series of six bis-alkylated compounds ranging from symmetric (PQ-11,11) to highly asymmetric (PQ-20,2) were prepared. Four themes of bioactivity emerged: (1) the most bioactive compounds were gemini in structure; (2) 22 carbons in the alkyl chains, with little to modest asymmetry, led to optimal activity; (3) bicephalic compounds were generally comparable to conventional amphiphiles, though only about 12 carbons in the alkyl chains were solubilized in water by each cationic nitrogen; (4) the effects of counterion identity were not evident between chlorides and bromides; however, the presence of the iodide counterion inhibited dissolution in all compounds tested. Three isomeric compounds with little to no asymmetry in tail length, PQ-11,11, PQ-12,10, and PQ-14,8, prepared as the bromide salts, showed comparable and highly potent activity, with MIC levels around 2 mu M against 3 of 4 bacteria tested. The simple (one-to two-step) syntheses of potent antimicrobials portend well for future optimization. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.079
• 作为产物：
  描述：

  4,4'-联吡啶 、 溴代十四烷 以 氯仿 、 乙腈 为溶剂， 生成 1-tetradecyl-4,4'-bipyridinium bromide
  参考文献：
  名称：

  基于水溶性电荷转移复合物的超分子两亲物：具有可调平直度的超长纳米纤维的制备

  摘要：

  从卷曲到笔直：电荷转移复合物的形成是由库仑吸引和电荷转移相互作用共同驱动的。从超分子两亲物获得的电荷转移络合物（见图）是水溶性的，并形成超长纳米纤维，其平直度可以通过改变反应溶液的pH值来调节。

  DOI：

  10.1002/anie.200903897

文献信息

• Charge-transfer interactions for the fabrication of multifunctional viral nanoparticles
  作者：Jun Hu、Peiyi Wang、Xia Zhao、Lin Lv、Song Yang、Baoan Song、Qian Wang

  DOI：10.1039/c4cc05195e

  日期：——

  In this paper, a facile strategy to fabricate multifunctional viral nanoparticles was described by introducing charge-transfer interactions between a pyrenyl motif with dinitrophenyl and pyridinium-contained guest molecules.

  在这篇论文中，介绍了一种简便的策略，通过在吡啶基团与二硝基苯基和含有吡啶基团的客体分子之间引入电荷转移相互作用来制备多功能病毒纳米颗粒。