5-[3,4-bis(3,7-(S)-dimethyl-6-octenyloxy)phenyl]tetrazole | 244020-34-6

• 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-[3,4-bis(3,7-(S)-dimethyl-6-octenyloxy)phenyl]tetrazole
• 英文别名: 5-[3,4-bis[(3S)-3,7-dimethyloct-6-enoxy]phenyl]-2H-tetrazole
• CAS: 244020-34-6
• 化学式: C₂₇H₄₂N₄O₂
• 分子量: 454.656
• InChiKey: JSMXSVPGOHMVJB-GOTSBHOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  33
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  72.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-[3,4-bis(3,7-(S)-dimethyl-6-octenyloxy)phenyl]tetrazole 、 1,3,5-苯三甲酰氯 在 吡啶 作用下， 反应 24.0h， 以39%的产率得到2-[3,5-bis[5-[3,4-bis[(3S)-3,7-dimethyloct-6-enoxy]phenyl]-1,3,4-oxadiazol-2-yl]phenyl]-5-[3,4-bis[(3S)-3,7-dimethyloct-6-enoxy]phenyl]-1,3,4-oxadiazole
  参考文献：
  名称：

  基于1,3,4-恶二唑的发光柱状液晶

  摘要：

  在这项研究中，合成了五种新化合物，即1,3,4-恶二唑的衍生物，以实现介晶行为和发光。为了研究醇盐基团对介晶行为的影响，使用了不同类型的脂族链。所有这些化合物在溶液和固体膜中均显示出高的热稳定性和强烈的蓝色光致发光。此外，化合物10a – d呈现六方柱状同构，其特征在于偏振光学显微镜和X射线衍射，并观察到强π堆积。值得注意的是，对于两种化合物（10c，d），从各向同性状态冷却至室温后，液晶特性得以保留。这些特性使这些材料成为有机电子产品的理想候选材料。

  DOI：

  10.1016/j.tet.2013.09.079
• 作为产物：
  描述：

  (S)-(+)-溴化香茅酯 在 sodium azide 、 三乙胺盐酸盐 、 potassium carbonate 、 potassium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 80.0h， 生成 5-[3,4-bis(3,7-(S)-dimethyl-6-octenyloxy)phenyl]tetrazole
  参考文献：
  名称：

  Bidirectional Association of Branched Noncovalent Complexes of Tetrazoles and 1,3,5-Tris(4,5-dihydroimidazol-2-yl)benzene in Solution

  摘要：

  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.

  DOI：

  10.1021/jo990830z

文献信息

• 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.
• Luminescent columnar liquid crystals based on 1,3,4-oxadiazole
  作者：Edivandro Girotto、Juliana Eccher、André A. Vieira、Ivan H. Bechtold、Hugo Gallardo

  DOI：10.1016/j.tet.2013.09.079

  日期：2014.5

  In this study five new compounds, derivatives of 1,3,4-oxadiazole, were synthesized in order to achieve mesomorphic behavior and luminescence. Different types of aliphatic chains were used in order to investigate the influence of alkoxide groups in mesomorphic behavior. All of the compounds showed high thermal stability and strong blue photoluminescence in solution and in solid films. Furthermore,

  在这项研究中，合成了五种新化合物，即1,3,4-恶二唑的衍生物，以实现介晶行为和发光。为了研究醇盐基团对介晶行为的影响，使用了不同类型的脂族链。所有这些化合物在溶液和固体膜中均显示出高的热稳定性和强烈的蓝色光致发光。此外，化合物10a – d呈现六方柱状同构，其特征在于偏振光学显微镜和X射线衍射，并观察到强π堆积。值得注意的是，对于两种化合物（10c，d），从各向同性状态冷却至室温后，液晶特性得以保留。这些特性使这些材料成为有机电子产品的理想候选材料。