5-(4-dodecyloxyphenyl)tetrazole | 244020-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(4-dodecyloxyphenyl)tetrazole
• 英文别名: 5-(4-dodecoxyphenyl)-2H-tetrazole
• CAS: 244020-32-4
• 化学式: C₁₉H₃₀N₄O
• 分子量: 330.473
• InChiKey: BSAIWKCMABJGCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  24
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  63.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-dodecyloxyphenyl)tetrazole 在 吡啶 、 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-{5-[4-(dodecyloxy)phenyl]-1,3,4-oxadiazol-2-yl}benzoic acid
  参考文献：
  名称：

  Luminescent columnar liquid crystals generated by self-assembly of 1,3,4-oxadiazole derivatives

  摘要：

  描述了五种衍生自 1,3,4-恶二唑的新型 V 型酸。这些化合物用于通过与 2,4-二氨基-6-十二烷基氨基-1,3,5-三嗪以 3 : 1 的氢键相互作用制备超分子复合物。通过红外和核磁共振技术证明了复合物的形成。通过偏光光学显微镜、差示扫描量热法和小角 X 射线衍射对所有配合物进行了研究。在室温下观察到配合物的矩形和六方柱状中间相，没有结晶迹象。圆二色性研究表明，在液晶状态下，这些材料表现出超分子光学活性。据推测，这种现象是由于螺旋柱状组织而产生的。此外，该配合物在溶液中和中间相中表现出强烈的蓝光发射，具有良好的光致发光量子产率。因此，这些材料可能成为光电应用的有希望的候选材料。

  DOI：

  10.1039/c0jm04570e
• 作为产物：
  描述：

  4-羟基苯甲腈 在 sodium azide 、 四丁基溴化铵 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-(4-dodecyloxyphenyl)tetrazole
  参考文献：
  名称：

  通过将 1,3,4-噁二唑与噻唑并[5,4-d]噻唑单元连接得到高发光液晶

  摘要：

  噻唑并[5,4-d]噻唑和两个 1,3,4-噁二唑单元之间的直接键合使我们能够为发光液晶创造一种新的多功能刚性核心，它显示出有趣且可变的介观和光物理特性。从 5-双（5-苯基-1,3,4-噁二唑-2-基）噻唑并[5,4-d]噻唑新核心中，合成了三个具有不同烷氧基链数的分子，其性质与分子结构相关。具有两条链的分子表现出 smectic C 中间相，而具有 4 条和 6 条链的中间生体呈现六方柱状中等同形，POM 和 XRD 测量证实了这一点。此外，具有六条链的分子表现出接近室温的液晶行为。在溶液中，分子呈现出从蓝色到黄色的强光致发光，量子产率高于 0.6。激发态寿命允许将与不同发射物质相关的荧光分量与旋涂薄膜中的分子组织相关联。分子能级，以及热稳定性和分子堆积可能引起的电荷载流子传输，表明这些分子在光电应用中很有前景。总体而言，这项工作有助于开发噻唑并[5,4-d]噻唑在液晶中的使用，证明了其出色的效率和多功能性。

  DOI：

  10.1016/j.molliq.2020.114887

文献信息

• H-bonded complexes containing 1,3,4-oxadiazole derivatives: mesomorphic behaviour, photophysical properties and chiral photoinduction
  作者：André A. Vieira、Emma Cavero、Pilar Romero、Hugo Gallardo、José Luis Serrano、Teresa Sierra

  DOI：10.1039/c4tc00886c

  日期：——

  supramolecular complexes through hydrogen bonding with 2,4-diamino-6-dodecylamino-1,3,5-triazine in a 3 : 1 ratio, respectively. The formation of the complexes was studied by infrared and NMR techniques. The thermal behaviour and mesomorphic properties of all the complexes were investigated by polarized light optical microscopy, differential scanning calorimetry and X-ray diffraction. Hexagonal and rectangular

  描述了衍生自1,3,4-恶二唑的两个系列的新V形酸。这些酸分别通过与3：1的2,4-二氨基-6-十二烷基氨基-1,3,5-三嗪氢键键合来制备超分子复合物。通过红外和核磁共振技术研究了配合物的形成。通过偏光光学显微镜，差示扫描量热法和X射线衍射研究了所有配合物的热行为和介晶性质。在室温下观察到所有配合物的六角形和矩形柱状中间相，没有结晶的迹象。圆二色性研究的结果使我们提出，在液晶状态下，这些材料采用螺旋圆柱状组织，并且可以通过CPL照射来控制手性。
• Tristriazolotriazines: a core for luminescent discotic liquid crystals
  作者：Rodrigo Cristiano、Hugo Gallardo、Adailton J. Bortoluzzi、Ivan H. Bechtold、Carlos E. M. Campos、Ricardo L. Longo

  DOI：10.1039/b810680k

  日期：——

  The synthesis and structural, thermal, optical and theoretical characterization of new tris[1,2,4]triazolo[1,3,5]triazines were performed to support their application as liquid crystals and advanced materials.

  进行了新的三[1,2,4]三唑并[1,3,5]三嗪的合成及结构，热，光学和理论表征，以支持其作为液晶和高级材料的应用。
• Room temperature columnar liquid crystalline phases of luminescent non-symmetric star-shaped molecules containing two 1,3,4-oxadiazole units
  作者：Eduard Westphal、Marko Prehm、Ivan H. Bechtold、Carsten Tschierske、Hugo Gallardo

  DOI：10.1039/c3tc31704h

  日期：——

  In the present work, we show the synthesis and full characterization of 12 new 1,3,4-oxadiazole non-symmetrical star-shaped molecules containing amide or imine connecting groups, variable number and positions of linear or branched alkoxy chains and different sizes of the aromatic core. Thermal and liquid crystalline properties were investigated by POM, DSC, TGA and XRD scattering, while photophysical

  在目前的工作中，我们显示了12个新的，具有酰胺或亚胺连接基团，线性或支链烷氧基链的数目和位置可变以及不同大小的酰胺的1,3,4-恶二唑非对称星形分子的合成和完整表征。芳香核。通过POM，DSC，TGA和XRD散射研究了热和液晶性质，同时在溶液和固态（薄膜）中实现了光物理研究（紫外可见吸收，发射和量子产率）。大多数化合物形成对映六角形柱状相，而所有分子均显示蓝色发光。热和光物理性质的变化与每个分子显示的不同结构参数相关。
• Cytotoxicity of η-areneruthenium-based molecules to glioblastoma cells and their recognition by multidrug ABC transporters
  作者：Jaqueline Pazinato、Otávio M. Cruz、Karine P. Naidek、Amanda R.A. Pires、Eduard Westphal、Hugo Gallardo、Hélène Baubichon-Cortay、Maria E.M. Rocha、Glaucia R. Martinez、Sheila M.B. Winnischofer、Attilio Di Pietro、Herbert Winnischofer

  DOI：10.1016/j.ejmech.2018.02.026

  日期：2018.3

  A new series of amphiphilic eta(6)-areneruthenium(II) compounds containing phenylazo ligands (group I: compounds la, 1b, 2a and 2b) and phenyloxadiazole ligands (group II: compounds 3a, 3b, 4a and 4b) were synthesized and characterized for their anti-glioblastoma activity. The effects of the amphiphilic eta(6)-areneruthenium(II) complexes on the viability of three human glioblastoma cell lines, U251, U87MG and T98G, were evaluated. The azo-derivative ruthenium complexes (group I) showed high cytotoxicity to all cell lines, whilst most oxadiazole-derivative complexes (group II) were less cytotoxic, except for compound 4a. The cationic complexes 2a, 2b and 4b were more cytotoxic than the neutral complexes. Compounds 2a and 2b caused a significant reduction in the percentage of cells in the G0/G1 phase, with concomitant increases in the G2/M phase and fragmented DNA in the T98G cell line. The eta(6)-areneruthenium(11) compounds were also tested in cell lines that overexpress the multidrug ABC transporters P-gp, MRP1 and ABCG2. Compounds 2b and 4a were substrates for the P-gp protein, with resistance indexes of 8.6 and 1.9, respectively. Compound 2b was also a substrate for ABCG2 and MRP1 proteins, with lower resistance indexes (1.8 and 1.6, respectively). The contribution of multidrug ABC transporters to the cytotoxicity of compound 2b in T98G cells was evidenced, since verapamil (a characteristic inhibitor of MRP1) increased the cytotoxicity of compound 2b at concentrations up to 20 mu mol L-1, whilst GP120918 and Ko143 (specific inhibitors of P-gp and ABCG2, respectively) had no significant effect. In addition, we showed that compound 2b interacts with glutathione (GSH), which could explain its cellular efflux by MRP1. Our results showed that the amphiphilic eta(6)-areneruthenium(II) complexes are promising anti-glioblastoma compounds, especially compound 2b, which was cytotoxic for all three cell lines, although it is transported by the three main multidrug ABC transporters. (C) 2018 Elsevier Masson SAS. All rights reserved.
• Bidirectional Association of Branched Noncovalent Complexes of Tetrazoles and 1,3,5-Tris(4,5-dihydroimidazol-2-yl)benzene in Solution
  作者：Arno Kraft、Frank Osterod、Roland Fröhlich

  DOI：10.1021/jo990830z

  日期：1999.8.1

  Noncovalent 3:1 complexes were obtained by combining acidic tetrazoles with the tribasic 1,3,5-tris(4,5-dihydroimidazol-2-yl)benzene (1). A branched structure and the use of solubilizing groups ensured that the resulting complexes dissolved in a range of nonpolar organic solvents. An X-ray crystal structure analysis of a model complex with tetrazole showed a completely planar, C-3-symmetrical, hydrogen-bonded molecule that salt-packed along the crystallographic c axis with an interplanar spacing of 3.31 Angstrom. Model binding studies between a tetrazolate and a protonated 1,3-bis(4,5-dihydroimidazol-2-yl)benzene allowed an association constant of 2470 +/- 400 M-1 to be measured in the competitive solvent mixture CDCl3/CD3OD (97:3). The ionic nature and the extended planarity of the tetrazole complexes' core favored the formation of supramolecular stacks not only in the solid, but also in (nonpolar) solution. Self-association was evidenced by NMR and CD spectroscopy as well as by vapor-pressure osmometry.