4-hexadecyloxypyridine | 212377-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hexadecyloxypyridine
• 英文别名: 4-Hexadecoxypyridine
• CAS: 212377-23-6
• 化学式: C₂₁H₃₇NO
• 分子量: 319.531
• InChiKey: WWDQLKRYJSPYGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  23.0
• 可旋转键数：
  16.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.76
• 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-hexadecyloxypyridine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 40.0h， 以91%的产率得到4-hexadecyloxypyridinium 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 、 1-十六烷醇 在 sodium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 25.0h， 生成 4-hexadecyloxypyridine
  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。
• Complexes of nickel(II) carboxylates with pyridine and cyclam: crystal structures, mesomorphisms, and thermoelectrical properties
  作者：Norbani Abdullah、Suhana Mohd Said、Yanti Yana Halid、Megat Muhammad Ikhsan Megat Hasnan、Naima Sharmin、Siti Amira Mat Hussin、Nik Muhd Jazli Nik Ibrahim、Abdul Rahman Nordin、Nurul Atikah Safiin、Nurul Shafinaz Anuar

  DOI：10.1080/00958972.2016.1221504

  日期：2016.10.1

  with p-(hexadecyloxy)pyridine (L) to form an ionic complex, [Ni(cyclam)(L)2](C6H5COO)2 (7). Complexes 3–6 were single crystals. All complexes have octahedral Ni(II) center(s) and were magnetic. Complexes with cyclam as co-ligand were more thermally stable than those with pyridine and its derivative, L. Complexes 3 and 4 were mesomorphic after partial loss of water and/or pyridine ligands on heating.

  摘要 羧酸镍 [Ni(CH3(CH2)14COO)2(H2O)2] (1) 和 [Ni(C6H5COO)2( )2] (2) 由 NiCl2·6 与 ( )14COONa 和 C6H5COONa，分别。配合物 1 与吡啶 (pyr) 反应生成 [Ni( ( )14COO)2(pyr)2( )2] (3) 和 [Ni2(μ2- )( ( )14COO)4(pyr) )4] (4) 在相同的反应混合物中，并与环丙烷反应形成离子络合物，[Ni( ( )14COO)(环丙烷)( )] ( )14COO·4 (5)。相比之下，2 与 cyclam 反应形成 [Ni(C6H5COO)2(cyclam)] (6)。最后，6 与对（十六烷氧基）吡啶 (L) 反应形成离子络合物 [Ni(cyclam)(L)2](C6H5COO)2 (7)。配合物
• Optimised thermally driven molecular stability of an SCO metal complex for TEC Seebeck generation enhancement
  作者：Megat Muhammad Ikhsan Megat Hasnan、Suhana Mohd Said、Mohd Faizul Mohd Sabri、Siti Amira Mat Hussin、Norbani Abdullah、Nik Muhd Jazli Nik Ibrahim、Yuzuru Miyazaki、Mohd Faiz Mohd Salleh、Noraisyah Mohd Shah

  DOI：10.1039/c9ra00779b

  日期：——

  complex to 1.94-fold that of a previously studied paramagnetic Co complex, and in a Fe(III)L16 complex to 3.43-fold that of a less diamagnetic Fe complex. We show with DSC studies of an Fe based octahedral complex that an endothermic absorption accompanies the spin crossover transition, which enhances the Seebeck coefficient of this metal complex. Thus, we can correlate the diamagnetic stabilisation

  热电效应允许在施加热梯度时在电解质中产生电势。在之前的工作中，金属配合物中的自旋交叉效应被证明有利于产生高塞贝克系数，因为伴随自旋状态变化的构象变化相关的高熵。在这项研究中，我们通过优化配体链长度来检查自旋交叉材料的抗磁稳定性。我们表明，自旋交叉材料的抗磁稳定性可以通过八面体结构的配体优化来增强热电化学塞贝克效应。碳链长度从 C 14增加到 C 16在 N 供体配体的长烷基链中，Co( III ) L16配合物中的 Seebeck 生成增加至先前研究的顺磁性 Co 配合物的 1.94 倍，而在 Fe( III ) L16 配合物中则增加了 3.43 倍。抗磁性较低的铁络合物。我们通过对 Fe 基八面体配合物的 DSC 研究表明，吸热吸收伴随自旋交叉跃迁，这提高了这种金属配合物的塞贝克系数。因此，我们可以将抗磁稳定性与温度相关联。因此，我们提出了一种优化自旋交叉金属配合物的分子设计策略。
• 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.