4-tetradecyloxypyridine | 1321654-96-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-tetradecyloxypyridine
• CAS: 1321654-96-9
• 化学式: C₁₉H₃₃NO
• 分子量: 291.477
• InChiKey: AIBMRXAOVKXNOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.16
• 重原子数：
  21.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-tetradecyloxypyridine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 40.0h， 以93%的产率得到4-tetradecyloxypyridinium chloride
  参考文献：
  名称：

  4-羟基吡啶衍生的离子液晶

  摘要：

  取决于烷基化的位点（N 或 O），4-羟基吡啶的单烷基化产生中性 N-烷基-4-吡啶酮或 4-烷氧基吡啶。这两种中性化合物的进一步烷基化产生了具有两条长烷基链的 N-烷基-4-烷氧基溴化吡啶的离子液晶 (ILC)。或者，两种中性化合物与 HCl 的简单质子化也诱导形成 N-烷基-4-羟基吡啶鎓氯化物或 4-烷氧基吡啶鎓盐酸盐的 ILC。通过单晶 X 射线衍射确定了两种不同类型的离子液晶和一种中性化合物的晶体结构。通过差示扫描量热法、偏光显微镜和粉末 X 射线衍射法检查中间相性质。阴离子影响二烷基化化合物中中间相的结构和稳定性。利用核磁共振扩散级谱技术研究了一些典型化合物在溶液中的自组装行为。最后，制备并表征了由吡啶鎓盐稳定的稳定的金纳米颗粒。

  DOI：

  10.1039/c0sm01376e
• 作为产物：
  描述：

  4-氯吡啶 、 十四醇 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 25.0h， 生成 4-tetradecyloxypyridine
  参考文献：
  名称：

  4-羟基吡啶衍生的离子液晶

  摘要：

  取决于烷基化的位点（N 或 O），4-羟基吡啶的单烷基化产生中性 N-烷基-4-吡啶酮或 4-烷氧基吡啶。这两种中性化合物的进一步烷基化产生了具有两条长烷基链的 N-烷基-4-烷氧基溴化吡啶的离子液晶 (ILC)。或者，两种中性化合物与 HCl 的简单质子化也诱导形成 N-烷基-4-羟基吡啶鎓氯化物或 4-烷氧基吡啶鎓盐酸盐的 ILC。通过单晶 X 射线衍射确定了两种不同类型的离子液晶和一种中性化合物的晶体结构。通过差示扫描量热法、偏光显微镜和粉末 X 射线衍射法检查中间相性质。阴离子影响二烷基化化合物中中间相的结构和稳定性。利用核磁共振扩散级谱技术研究了一些典型化合物在溶液中的自组装行为。最后，制备并表征了由吡啶鎓盐稳定的稳定的金纳米颗粒。

  DOI：

  10.1039/c0sm01376e

文献信息

• Synthesis of 4-alkoxypyridines as intermediates for zwitterionic liquid crystals
  作者：Anas N. Hajhussein、Loay S. Abuzahra、Anna Pietrzak、Mary F. Sadek、Muhammad O. Ali、Jakub Wojciechowski、Andrienne C. Friedli、Piotr KaszyÅ„ski

  DOI：10.24820/ark.5550190.p010.700

  日期：——

  A series of 4-alkoxypyridines with n = 5–18 was obtained in typical yields of 75-80% by reacting 4-chloropyridine hydrochloride with the appropriate alcohol in DMSO in the presence of powdered NaOH. The reported synthesis is compared to other methods for preparation of 4-alkoxypyridines, and their uses are reviewed. 4-Tridecyloxypyridine is converted into the bis-zwitterionic derivative of [closo-B10H10]

  在粉末 NaOH 存在下，通过 4-氯吡啶盐酸盐与适当的醇在 DMSO 中反应，以 75-80% 的典型收率获得了一系列 n = 5-18 的 4-烷氧基吡啶。将报告的合成与其他制备 4-烷氧基吡啶的方法进行比较，并对其用途进行了审查。4-十三烷氧基吡啶转化为 [closo-B10H10] 的双两性离子衍生物，呈现液晶相和软结晶相。通过单晶XRD方法建立了两种吡啶和双两性离子的固态结构。研究了 N 原子配位对吡啶环几何形状的影响。
• Highly quadrupolar derivatives of the [closo-B10H10]2- anion: Investigation of liquid crystalline polymorphism in an homologous series of 1,10-bis(4-alkoxypyridinium) zwitterions
  作者：Muhammad O. Ali、Damian Pociecha、Jakub Wojciechowski、Irina Novozhilova、Andrienne C. Friedli、Piotr Kaszyński

  DOI：10.1016/j.jorganchem.2018.04.003

  日期：2018.6

  A series of pyridinium bis-zwitterions [closo-B10H8-1,10-2 (4-ROC5H4N)] (1[u]) was obtained in 55-60% yield by reacting [closo-B10H8-1,10-2(1Ph)] (3) with 4-alkoxypyridines and the resulting derivatives were analyzed for their liquid crystalline properties. Optical, thermal and XRD analyses revealed the formation of a nematic and rare lamellar phases, Lama, driven by dipolar interactions. Upon elongation of the terminal alkoxy chain, the nematic phase is gradually replaced by the lamellar polymorphism. The solidstate structures of 1[8], 1[12] and 1[16] were established by single crystal XRD:1[12] p-1,z=2,a= 9.6262 (2) angstrom,b = 12.0464(2) angstrom, c=12.611150(10) angstrom,beta=103.9910(10)degrees;1[12] p-1,Z=2,a=9.6262,(2) angstrom,b = 12.0464(2) angstrom, c=17.9226(3)angstrom, alpha=80.5940(10)degrees, beta= 83.0700(10)degrees, gamma=74.9860(10)degrees; 1[16] p-1, Z=2,a=9.6827 (3) angstrom,b = 11.6711 (5) angstrom, c= 22.8486(7) angstrom, alpha=77.416(3)degrees, beta = 86.925(2)degrees,gamma=66.202 (4)Alpha degrees
• Synthesis and Validation of TRIFAPYs as a Family of Transfection Agents for Therapeutic Oligonucleotides
  作者：Berta Isanta、Ana Delgado、Carlos J. Ciudad、Mª Antònia Busquets、Rosa Griera、Núria Llor、Véronique Noé

  DOI：10.3390/biom14040390

  日期：——

  Transfection agents play a crucial role in facilitating the uptake of nucleic acids into eukaryotic cells offering potential therapeutic solutions for genetic disorders. However, progress in this field needs the development of improved systems that guarantee efficient transfection. Here, we describe the synthesis of a set of chemical delivery agents (TRIFAPYs) containing alkyl chains of different lengths based on the 1,3,5-tris[(4-alkyloxy-1pyridinio)methyl]benzene tribromide structure. Their delivery properties for therapeutic oligonucleotides were evaluated using PolyPurine Reverse Hoogsteen hairpins (PPRHs) as a silencing tool. The binding of liposomes to PPRHs was evaluated by retardation assays in agarose gels. The complexes had a size of 125 nm as determined by DLS, forming well-defined concentrical vesicles as visualized by Cryo-TEM. The prostate cancer cell line PC-3 was used to study the internalization of the nanoparticles by fluorescence microscopy and flow cytometry. The mechanism of entrance involved in the cellular uptake was mainly by clathrin-mediated endocytosis. Cytotoxicity analyses determined the intrinsic toxicity caused by each TRIFAPY and the effect on cell viability upon transfection of a specific PPRH (HpsPr-C) directed against the antiapoptotic target survivin. TRIFAPYs C12-C18 were selected to expand these studies in the breast cancer cell line SKBR-3 opening the usage of TRIFAPYs for both sexes and, in the hCMEC/D3 cell line, as a model for the blood–brain barrier. The mRNA levels of survivin decreased, while apoptosis levels increased upon the transfection of HpsPr-C with these TRIFAPYs in PC-3 cells. Therefore, TRIFAPYs can be considered novel lipid-based vehicles for the delivery of therapeutic oligonucleotides.