1-tetradecyl-1'-methyl-4,4'-bipyridinium bromide iodide | 1383253-39-1

• 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-1'-methyl-4,4'-bipyridinium bromide iodide
• 英文别名: 1-Methyl-4-(1-tetradecylpyridin-1-ium-4-yl)pyridin-1-ium;bromide;iodide
• CAS: 1383253-39-1
• 化学式: Br*C₂₅H₄₀N₂*I
• 分子量: 575.414
• InChiKey: NLBPLPALOAGBRC-UHFFFAOYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  0.17
• 重原子数：
  29
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  7.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-tetradecyl-1'-methyl-4,4'-bipyridinium bromide iodide 在 Amberlite IRA-400 resin chloride form 作用下， 以 甲醇 为溶剂， 生成 1-methyl-1'-tetradecylviologen
  参考文献：
  名称：

  链长在甲基烷基紫精的葫芦[8]尿素络合中的作用

  摘要：

  在水中研究了烷基链长度对四种甲基紫胶单体（MVCn，n = 12、14、16、18）与葫芦[8] uril（CB [8]）结合模式的影响，揭示了从从12到16个碳原子移动的化学计量比为1：1至2：1。通过CB [8] 2 -MVC18配合物的晶体结构测定，获得了固态化学计量比为2：1的前所未有的证据。

  DOI：

  10.1002/ejoc.202100014
• 作为产物：
  描述：

  4,4'-联吡啶 以 乙腈 为溶剂， 反应 49.0h， 生成 1-tetradecyl-1'-methyl-4,4'-bipyridinium bromide iodide
  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

文献信息

• Supramolecular Amphiphiles Based on a Water-Soluble Charge-Transfer Complex: Fabrication of Ultralong Nanofibers with Tunable Straightness
  作者：Chao Wang、Yinsheng Guo、Yapei Wang、Huaping Xu、Ruji Wang、Xi Zhang

  DOI：10.1002/anie.200903897

  日期：2009.11.9

  From curly to straight: The formation of a charge‐transfer complex is driven by the combination of Coulombic attraction and charge transfer interactions. The charge‐transfer complex which is obtained from a supramolecular amphiphile (see picture) is water‐soluble and forms ultralong nanofibers, the straightness of which can be modulated by changing the pH of the reaction solution.

  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。
• The antibacterial activity of 4,4′-bipyridinium amphiphiles with conventional, bicephalic and gemini architectures
  作者：Melissa C. Grenier、Robert W. Davis、Kelsey L. Wilson-Henjum、Jade E. LaDow、Jacob W. Black、Kevin L. Caran、Kyle Seifert、Kevin P.C. Minbiole

  DOI：10.1016/j.bmcl.2012.04.079

  日期：2012.6

  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.
• The Role of Chain Length in Cucurbit[8]uril Complexation of Methyl Alkyl Viologens
  作者：Alessandro Pedrini、Anjali Devi Das、Roberta Pinalli、Neal Hickey、Silvano Geremia、Enrico Dalcanale

  DOI：10.1002/ejoc.202100014

  日期：2021.3.12

  The influence of alkyl chain length on the binding mode of four methyl alkyl viologens (MVCn with n=12,14,16,18) with cucurbit[8]uril (CB[8]) was investigated in water, revealing a clear switch from 1 : 1 to 2 : 1 stoichiometry moving from 12 to 16 carbon atoms. An unprecedented evidence of the 2 : 1 stoichiometry in the solid state was obtained by crystal structure determination of CB[8]2−MVC18 complex

  在水中研究了烷基链长度对四种甲基紫胶单体（MVCn，n = 12、14、16、18）与葫芦[8] uril（CB [8]）结合模式的影响，揭示了从从12到16个碳原子移动的化学计量比为1：1至2：1。通过CB [8] 2 -MVC18配合物的晶体结构测定，获得了固态化学计量比为2：1的前所未有的证据。