4-methyl-1-octadecylpyridin-1-ium bromide | 38325-98-3

• 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: 4-methyl-1-octadecylpyridin-1-ium bromide
• 英文别名: 4-methyl-1-octadecylpyridinium bromide；4-methyl-1-octadecylpyridin-1-ium;bromide
• CAS: 38325-98-3
• 化学式: Br*C₂₄H₄₄N
• 分子量: 426.524
• InChiKey: ZZIRYYZPPBWRGH-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-methyl-1-octadecylpyridin-1-ium bromide 在 高氯酸 作用下， 以 乙醇 为溶剂， 以3.03 g的产率得到4-methyl-1-octadecylpyridinium perchlorate
  参考文献：
  名称：

  基于苯乙烯染料的分子转子。分子碎片旋转的粘度依赖性

  摘要：

  合成了三种供体-受体苯乙烯基染料 R-Het+-CH=CH-C6H4-NR'R″ClO4-（Het 是吡啶基）。它们的光谱发光行为允许将它们分配给一类分子转子。研究了介质的粘度、极性和温度对其吸收和荧光特性的影响。随着介质粘度的增加和温度的降低，观察到染料荧光的显着增强，伴随着荧光最大值的短波长偏移。聚甲基丙烯酸甲酯薄膜中染料在 293 和 77 K 下的荧光光谱测量证实了介质粘度对光激发时分子碎片旋转能力的影响。根据量子化学计算，在非极性溶剂中苯乙烯染料的激发分子中，分子片段主要围绕中心乙烯键 $(HC\underline \cdots CH)$ 旋转。在极性溶剂中，围绕乙烯片段普通键的旋转势垒会降低。

  DOI：

  10.1007/s11172-014-0660-1
• 作为产物：
  描述：

  4-甲基吡啶 、 硬脂基溴 反应 1.5h， 生成 4-methyl-1-octadecylpyridin-1-ium bromide
  参考文献：
  名称：

  基于苯乙烯染料的分子转子。分子碎片旋转的粘度依赖性

  摘要：

  合成了三种供体-受体苯乙烯基染料 R-Het+-CH=CH-C6H4-NR'R″ClO4-（Het 是吡啶基）。它们的光谱发光行为允许将它们分配给一类分子转子。研究了介质的粘度、极性和温度对其吸收和荧光特性的影响。随着介质粘度的增加和温度的降低，观察到染料荧光的显着增强，伴随着荧光最大值的短波长偏移。聚甲基丙烯酸甲酯薄膜中染料在 293 和 77 K 下的荧光光谱测量证实了介质粘度对光激发时分子碎片旋转能力的影响。根据量子化学计算，在非极性溶剂中苯乙烯染料的激发分子中，分子片段主要围绕中心乙烯键 $(HC\underline \cdots CH)$ 旋转。在极性溶剂中，围绕乙烯片段普通键的旋转势垒会降低。

  DOI：

  10.1007/s11172-014-0660-1

文献信息

• Antifungal activity of styrylpyridinium compounds against <i>Candida albicans</i>
  作者：Simona Vaitkienė、Neringa Kuliešienė、Sandra Sakalauskaitė、Laura Bekere、Laura Krasnova、Brigita Vigante、Gunars Duburs、Rimantas Daugelavičius

  DOI：10.1111/cbdd.13777

  日期：2021.2

  γ‐picoline with appropriate alkyl bromide and further condensation with substituted benzaldehyde. Compounds with long N‐alkyl chains (C18H37–C20H41) had no antifungal activity against the cells of all tested C. albicans strains. Other styrylpyridinium compounds were able to inhibit yeast growth at the concentrations of 0.06–16 μg/ml. At fungicidal concentrations, the compound with the CN‐ group was least

  为了评估对白色念珠菌细胞的抗真菌活性，我们合成了一组 13 种新的和较早描述的苯乙烯基吡啶鎓化合物（N-烷基苯乙烯基吡啶鎓盐与溴化物或甲苯磺酸盐），以评估与氟康唑可能的协同作用，并评估对哺乳动物的细胞毒性。细胞。所有化合物都是根据众所周知的两步程序合成的，包括用适当的烷基溴对 γ-甲基吡啶进行烷基化，然后与取代的苯甲醛进一步缩合。具有长N-烷基链( C 18 H 37 –C 20 H 41 ) 的化合物对所有测试的细胞均无抗真菌活性白色念珠菌菌株。其他苯乙烯基吡啶化合物能够在 0.06–16 μg/ml 的浓度下抑制酵母生长。在杀真菌浓度下，带有 CN- 基团的化合物对哺乳动物细胞的毒性最小，与氟康唑的协同作用最有效，对白色念珠菌的呼吸作用仅有轻微抑制。具有 4'-二乙氨基的化合物表现出最强的杀菌特性，并有效地阻断了白色念珠菌细胞的呼吸作用。然而，对哺乳动物细胞的毒性也很高。总而言之，我们
• Synthesis and mesophase behaviour of ionic liquid crystals
  作者：D. Ster、U. Baumeister、J. Lorenzo Chao、C. Tschierske、G. Israel

  DOI：10.1039/b705519f

  日期：——

  N-Alkyl-pyridinium derivatives 1–3 and N-alkyl-stilbazolium halides 4–6 with hydroxy, methoxy and hydrogen 4′-substituents and long non-branched alkyl chains (n = 14, 16, 18, 20, 22) were synthesized and characterized by polarizing microscopy, differential scanning calorimetry and X-ray measurements. The compounds exhibit liquid crystalline SmA phases when heated above their melting point. Phenyl substitution in the 3- and 4-position of the pyridinium ring causes a large tendency to decrease the clearing temperature in comparison to the 4-methyl substituted N-alkyl-pyridinium salts. By elongation of the pyridinium ring to the 4′-substituted stilbazolium unit the clearing points of the new compounds 4–6 increase drastically up to temperatures ≥200 °C in which partial decomposition of the compounds sets in. The length of the alkyl chains and the type of counter ions have large influences on the stability of the mesophase. Elongation of the alkyl chain length n increases the temperature range of the liquid crystalline phase. The counter ions increase the stability of the SmA phase in order Cl− > Br− > I− > BPh4−. When CH3–C6H5SO3− is introduced as an anion no liquid crystalline phase can be observed. UV/Vis measurements indicate the presence of a charge-transfer complex between the pyridinium cation and the iodide anion. Differences in the liquid crystalline behaviour of N-alkyl-4′-substituted stilbazolium halides 4–6 compared with N-alkyl-3- and -4-substituted-pyridinium derivatives 1–3 may be explained by additional intramolecular charge-transfer and resulting strong dipole–dipole interactions between stilbazolium compounds.

  合成并表征了具有羟基、甲氧基和氢的4′-取代基以及长的非分支烷基链（n = 14、16、18、20、22）的N-烷基吡啶鎓衍生物1–3和N-烷基斯替巴唑鎓卤化物4–6，采用了偏振显微镜、差示扫描量热法和X射线测量。化合物在加热至其熔点以上时表现出液晶SmA相。吡啶环3位和4位的苯基取代导致其清晰温度相较于4-甲基取代的N-烷基吡啶盐大幅降低。通过将吡啶环延伸至4′-取代的斯替巴唑鎓单元，新化合物4–6的清晰点大幅增加，达到≥200 °C的温度，在此温度下化合物开始部分分解。烷基链的长度和对离子的类型对中间相的稳定性有较大影响。烷基链长度n的延长增加了液晶相的温度范围。对离子按照Cl− > Br− > I− > BPh4−的顺序增加了SmA相的稳定性。当引入CH3–C6H5SO3−作为阴离子时，无法观察到液晶相。UV/Vis测量表明吡啶鎓阳离子和碘离子之间存在电荷转移复合物。与N-烷基-3和-4取代的吡啶衍生物1–3相比，N-烷基-4′-取代的斯替巴唑鎓卤化物4–6在液晶行为上的差异可以通过额外的分子内电荷转移和斯替巴唑化合物之间强的偶极-偶极相互作用来解释。
• Dye–Surfactant Interaction: Role of an Alkyl Chain in the Localization of Styrylpyridinium Dyes in a Hydrophobic Force Field of a Cationic Surfactant (CTAB)
  作者：Amaresh Mishra、Sanjukta Patel、Rajani K. Behera、Bijaya K. Mishra、Gopa B. Behera

  DOI：10.1246/bcsj.70.2913

  日期：1997.12

  The interaction of a number of cationic dyes (I) with a varying number of methylene groups (Cn) in the alkyl chain attached to pyridyl nitrogen with a cationic surfactant (CTAB) assembly is reported. The binding constant of the dyes (C5 to C18) with the micelle have been calculated, and are found to increase with increasing carbon chain. A plot of the binding constant vs. the chain length shows a curve with a maximum for C16, which is attributed to a compatibility factor. From studies of the electronic and emission spectra it is proposed that a micelle has a hydrophobic force field and that the dyes are localized in various pockets of the field.

  报告了一些阳离子染料（I）与阳离子表面活性剂（CTAB）的相互作用，这些阳离子染料（I）的烷基链中有不同数量的亚甲基（Cn）连接到吡啶氮上的阳离子表面活性剂（CTAB）组件中。通过计算发现，染料（C5 至 C18）与胶束的结合常数随碳链的增加而增加。结合常数与链长的关系曲线显示，C16 的结合常数最大，这归因于相容性因素。通过对电子和发射光谱的研究，提出胶束具有疏水力场，染料被定位在力场的不同口袋中。
• Aggregation induced emission switching and electrical properties of chain length dependent π-gels derived from phenylenedivinylene bis-pyridinium salts in alcohol–water mixtures
  作者：Suman K. Samanta、Santanu Bhattacharya

  DOI：10.1039/c2jm35012b

  日期：——

  Supramolecular π-gels were formed in a mixture of aliphatic alcohols and water for a series of chromophoric phenylenedivinylene bis-N-alkyl pyridinium salts (PPV) appended with terminal aliphatic hydrocarbon chains of different lengths. Gelation could be controlled either by altering the ratio of various alcohol–water mixtures or by changing the aliphatic chain length of the gelator. The temperature- and the ratio-variation in the ethanol–water mixtures exhibited a tunable emission behavior depending on the extent of aggregation which was promoted by aromatic π-stacking, van der Waals and electrostatic interactions among the individual PPV units. Thus, a light-blue emission at higher temperature (>40 °C), a reddish-orange emission at low temperature (<20 °C) and a white-light emission at room temperature (25–30 °C) were observed in solution. The gelators possessing longer aliphatic chains exhibited a higher gel-melting temperature, increased viscoelasticity and shorter fiber diameter based on a delicate hydrophobic/hydrophilic balance. A semiconducting nature of the electrical conductivity was observed for the individual compounds and the magnitude of the current increased with increasing width of the gel fibers upon decreasing the aliphatic chain length. A reversible one-electron redox behavior was observed for the chromophore and the redox potential decreased with the increase in the chain length. A diffusion-controlled redox behavior was observed for the gelators with shorter aliphatic chains. However, the compounds with longer chains made the process diffusion-limited.

  在脂肪醇和水的混合物中形成超分子α-凝胶，形成一系列带有不同长度末端脂肪烃链的发色亚苯基双-N-烷基吡啶鎓盐（PPV）。可以通过改变各种醇与水混合物的比例或改变胶凝剂的脂肪链长度来控制胶凝。乙醇-水混合物中的温度和比例变化表现出可调节的发射行为，具体取决于聚集程度，这是由芳香族β堆积、范德华力和各个PPV单元之间的静电相互作用促进的。因此，在较高温度（>40°C）下发出淡蓝色光，在低温（<20°C）下发出红橙色光，在室温（25-30°C）下发出白光）在溶液中观察到。具有较长脂肪链的胶凝剂基于微妙的疏水/亲水平衡表现出较高的凝胶熔融温度、增加的粘弹性和较短的纤维直径。观察到各个化合物的电导率的半导体性质，并且当脂肪链长度减小时，电流的大小随着凝胶纤维宽度的增加而增加。观察到发色团的可逆单电子氧化还原行为，并且氧化还原电位随着链长度的增加而降低。对于具有较短脂肪链的胶凝剂，观察到扩散控制的氧化还原行为。然而，具有较长链的化合物使得该过程的扩散受到限制。
• A New Fluorescent Probe for Selective Cd²⁺ Detection and Cell Imaging
  作者：Wenxin Lin、Xiaochun Xie、Yijia Wang、Jianjun Chen

  DOI：10.1002/zaac.201800454

  日期：2019.4.30

  A new highly selective fluorescent probe, (E)‐4‐(4‐([2,2′:6′,2′′‐terpyridin]‐4′‐yl)styryl)‐1‐octadecylpyridin‐1‐ium bromide (ZC‐F8), was designed and synthesized for cadmium detection and cell imaging. The fluorescence spectra of ZC‐F8 exhibited its excellent response towards Cd2+ via intramolecular charge transfer effect and aggregation induced emission effect. The cell‐imaging experiment was carried

  一种新的高选择性荧光探针（E）-4-（4-（[[2,2'：6'，2''-terpyridin] -4-4'-yl）styryl）-1-十八烷基吡啶-1-溴化铵（ ZC-F8）是为镉检测和细胞成像而设计和合成的。ZC-F8的荧光光谱通过分子内电荷转移效应和聚集诱导的发射效应表现出对Cd 2+的出色响应。进行细胞成像实验以评估ZC-F8的实际生物学应用。该探针对镉显示出理想的膜渗透性和标记特性，表明其在活细胞中金属离子检测和示踪方面的应用前景广阔。