1-hexadecyl-4-methylpyridinium bromide | 2315-40-4

• 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-hexadecyl-4-methylpyridinium bromide
• 英文别名: N-hexadecyl-4-methylpyridinium bromide；1-cetyl-4-methylpyridinium bromide；4-methylpyridiniumcetyl bromide；1-hexadecyl-4-methyl-pyridinium; bromide；1-Hexadecyl-4-methyl-pyridinium; Bromid；Cetylpicolinium bromide；1-hexadecyl-4-methylpyridin-1-ium;bromide
• CAS: 2315-40-4
• 化学式: Br*C₂₂H₄₀N
• 分子量: 398.47
• InChiKey: UFXSTPIFUFQVRP-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.77
• 重原子数：
  24
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-(十六烷氧基)苯甲醛 、 1-hexadecyl-4-methylpyridinium bromide 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 1-cetyl-4-(p-cetyloxystyryl)pyridinium bromide
  参考文献：
  名称：

  Sahay, A. K.; Mishra, B. K.; Behera, G. B., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1988, vol. 27, # 7, p. 561 - 564

  摘要：

  DOI：
• 作为产物：
  描述：

  4-甲基吡啶 、 溴代十六烷 反应 4.0h， 以72%的产率得到1-hexadecyl-4-methylpyridinium bromide
  参考文献：
  名称：

  二茂铁两亲性D–π–A染料：合成，氧化还原行为和带隙的确定†

  摘要：

  我们报告的一系列二茂铁的两亲性的供体- π-受体染料的合成，与通式（FC-CH CH-HetNC 16 ħ 33）+ X - [式中：Fc结构表现为所述供体基团，双键为π桥，和2-，4-吡啶和4-喹啉鎓作为有效的受体基团（图2a-b和4，X为Br -或BF 4 -）]，在良好的整体产量。以及中立的同行（6a–b和7），通过紫外可见光谱和循环伏安法研究了这些化合物的光物理和电化学性质。计算了这些染料的光学和电化学带隙，这表明4具有最低的带隙值。随时间变化的DFT计算表明，这些化合物显示的最低能量吸收带主要具有金属到配体的电荷转移特性，其中HOMO-LUMO电子跃迁是主要的贡献。

  DOI：

  10.1039/c8nj00787j

文献信息

• 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。
• Wide-Antimicrobial Spectrum of Picolinium Salts
  作者：Sarka Salajkova、Marketa Benkova、Jan Marek、Radek Sleha、Lukas Prchal、David Malinak、Rafael Dolezal、Kristina Sepčić、Nina Gunde-Cimerman、Kamil Kuca、Ondrej Soukup

  DOI：10.3390/molecules25092254

  日期：——

  Nosocomial infections, which greatly increase morbidity among hospitalized patients, together with growing antibiotic resistance still encourage many researchers to search for novel antimicrobial compounds. Picolinium salts with different lengths of alkyl chains (C12, C14, C16) were prepared by Menshutkin-like reaction and evaluated with respect to their biological activity, i.e., lipophilicity and critical micellar concentration. Picolinium salts with C14 and C16 side chains achieved similar or even better results when in terms of antimicrobial efficacy than benzalkoniums; notably, their fungicidal efficiency was substantially more potent. The position of the methyl substituent on the aromatic ring does not seem to affect antimicrobial activity, in contrast to the effect of length of the N-alkyl chain. Concurrently, picolinium salts exhibited satisfactory low cytotoxicity against mammalian cells, i.e., lower than that of benzalkonium compounds, which are considered as safe.

  医院感染极大增加了住院患者的发病率，加之不断增长的抗生素抗性，仍然鼓励许多研究人员寻找新型抗菌化合物。通过Menshutkin样反应制备了具有不同烷基链长度（C12、C14、C16）的吡啶盐，并针对它们的生物活性，即亲脂性和临界胶束浓度进行了评估。具有C14和C16侧链的吡啶盐在抗菌效力方面取得了类似甚至更好的结果，与苯扎溴铵相比；值得注意的是，它们的杀真菌效果明显更强。芳香环上甲基取代基的位置似乎不影响抗菌活性，与N-烷基链长度的影响形成对比。同时，吡啶盐对哺乳动物细胞表现出令人满意的低细胞毒性，即低于苯扎溴铵化合物，被认为是安全的。
• 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。
• Styrylpyridinium Derivatives for Fluorescent Cell Imaging
  作者：Reinis Putralis、Ksenija Korotkaja、Martins Kaukulis、Zhanna Rudevica、Juris Jansons、Olga Nilova、Martins Rucins、Laura Krasnova、Ilona Domracheva、Mara Plotniece、Karlis Pajuste、Arkadij Sobolev、Felikss Rumnieks、Laura Bekere、Anna Zajakina、Aiva Plotniece、Gunars Duburs

  DOI：10.3390/ph16091245

  日期：——

  A set of styrylpyridinium (SP) compounds was synthesised in order to study their spectroscopic and cell labelling properties. The compounds comprised different electron donating parts (julolidine, p-dimethylaminophenyl, p-methoxyphenyl, 3,4,5-trimethoxyphenyl), conjugated linkers (vinyl, divinyl), and an electron-withdrawing N-alkylpyridinium part. Geminal or bis-compounds incorporating two styrylpyridinium (bis-SP) moieties at the 1,3-trimethylene unit were synthesised. Compounds comprising a divinyl linker and powerful electron-donating julolidine donor parts possessed intensive fluorescence in the near-infrared region (maximum at ~760 nm). The compounds had rather high cytotoxicity towards the cancerous cell lines HT-1080 and MH-22A; at the same time, basal cytotoxicity towards the NIH3T3 fibroblast cell line ranged from toxic to harmful. SP compound 6e had IC50 values of 1.0 ± 0.03 µg/mL to the cell line HT-1080 and 0.4 µg/mL to MH-22A; however, the basal toxicity LD50 was 477 mg/kg (harmful). The compounds showed large Stokes’ shifts, including 195 nm for 6a,b, 240 nm for 6e, and 325 and 352 nm for 6d and 6c, respectively. The highest photoluminescence quantum yield (PLQY) values were observed for 6a,b, which were 15.1 and 12.2%, respectively. The PLQY values for the SP derivatives 6d,e (those with a julolidinyl moiety) were 0.5 and 0.7%, respectively. Cell staining with compound 6e revealed a strong fluorescent signal localised in the cell cytoplasm, whereas the cell nuclei were not stained. SP compound 6e possessed self-assembling properties and formed liposomes with an average diameter of 118 nm. The obtained novel data on near-infrared fluorescent probes could be useful for the development of biocompatible dyes for biomedical applications.

  为了研究苯乙烯吡啶（SP）化合物的光谱和细胞标记特性，我们合成了一组苯乙烯吡啶（SP）化合物。这些化合物由不同的电子捐赠部分（julolidine、对二甲氨基苯基、对甲氧基苯基、3,4,5-三甲氧基苯基）、共轭连接体（乙烯基、二乙烯基）和一个电子抽离的 N-烷基吡啶鎓部分组成。合成了在 1,3-三亚甲基单元上含有两个苯乙烯基吡啶鎓（双-SP）分子的双原子或双原子化合物。由二乙烯基连接体和强电子供体部分组成的化合物在近红外区域（约 760 纳米处为最大值）具有强烈的荧光。这些化合物对癌细胞系 HT-1080 和 MH-22A 具有相当高的细胞毒性；同时，对 NIH3T3 成纤维细胞系的基础细胞毒性从有毒到有害不等。SP 化合物 6e 对细胞株 HT-1080 的 IC50 值为 1.0 ± 0.03 µg/mL，对 MH-22A 的 IC50 值为 0.4 µg/mL；然而，其基础毒性 LD50 为 477 mg/kg（有害）。这些化合物显示出较大的斯托克斯位移，其中 6a,b 为 195 纳米，6e 为 240 纳米，6d 和 6c 分别为 325 纳米和 352 纳米。6a,b 的光量子产率（PLQY）值最高，分别为 15.1% 和 12.2%。SP 衍生物 6d、e（具有一个茱莉烷基的衍生物）的光量子产率分别为 0.5% 和 0.7%。用化合物 6e 进行细胞染色时，发现细胞胞质中有强烈的荧光信号，而细胞核则没有被染色。SP 化合物 6e 具有自组装特性，可形成平均直径为 118 nm 的脂质体。所获得的有关近红外荧光探针的新数据有助于开发生物医学应用领域的生物相容性染料。