1-bromo-5-[4-(4-butylophenylazo)phenoxy]pentane | 215095-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 1-bromo-5-[4-(4-butylophenylazo)phenoxy]pentane
• 英文别名: [4-(5-Bromopentoxy)phenyl]-(4-butylphenyl)diazene
• CAS: 215095-99-1
• 化学式: C₂₁H₂₇BrN₂O
• 分子量: 403.362
• InChiKey: ZQGVBJBBFNYISH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-bromo-5-[4-(4-butylophenylazo)phenoxy]pentane 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 5-[4-[(4-Butylphenyl)diazenyl]phenoxy]pentane-1-thiol
  参考文献：
  名称：

  A Convenient Synthesis of Novel Mercapto-Ended Azobenzene Derivatives

  摘要：

  Treatment of the product from the Diazo-Coupling reaction of p-alkylaniline with 1,3-dibromopropane in THF affords intermediate compounds n-C(n)H(2n+1)AzoO(CH2)(m)Br. Subsequent treatment of these intermediate with thiourea in ethanol at reflux temperature leads to the desired azobenzene derivatives, n-C(n)H(2n+1)AzoO(CH2)(m)SH (n=4,6,8,10,12; m=3,5), in good yield. The structure data of these new compounds was presented in detail.

  DOI：

  10.1080/00397919808004930
• 作为产物：
  描述：

  4-正丁基苯胺 在 盐酸 、 氢氧化钾 、 sodium carbonate 、 sodium nitrite 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 1-bromo-5-[4-(4-butylophenylazo)phenoxy]pentane
  参考文献：
  名称：

  A Convenient Synthesis of Novel Mercapto-Ended Azobenzene Derivatives

  摘要：

  Treatment of the product from the Diazo-Coupling reaction of p-alkylaniline with 1,3-dibromopropane in THF affords intermediate compounds n-C(n)H(2n+1)AzoO(CH2)(m)Br. Subsequent treatment of these intermediate with thiourea in ethanol at reflux temperature leads to the desired azobenzene derivatives, n-C(n)H(2n+1)AzoO(CH2)(m)SH (n=4,6,8,10,12; m=3,5), in good yield. The structure data of these new compounds was presented in detail.

  DOI：

  10.1080/00397919808004930

文献信息

• Supramolecular dimeric liquid crystals. The liquid crystalline behaviour of mixtures ofα-(4-pyridyloxy)-ω -[4-(4-butylphenylazo)phenoxy]alkanes and 4-octyloxybenzoic acid
  作者：Marc J. Wallage、Corrie T. Imrie

  DOI：10.1039/a700848a

  日期：——

  The thermal behaviour of binary mixtures of 1-(4-pyridyloxy)-5-[4-(4-butylphenylazo)phenoxy]pentane (Bu-azo-5-Pyr) and 1-(4-pyridyloxy)-6-[4-(butylphenylazo)phenoxy]hexane (Bu-azo-6-Pyr) with 4-octyloxybenzoic acid is reported. Both systems are miscible over the complete composition range; this miscibility is attributed to the formation of a hydrogen bond between the unlike species, a view confirmed by IR spectroscopy. Bu-azo-5-Pyr and Bu-azo-6-Pyr do not exhibit liquid crystallinity but enhanced liquid crystal behaviour is observed for the mixtures with the acid. In particular, smectic A behaviour is injected into the phase diagrams of both systems. The clearing temperatures of the mixtures containing Bu-azo-6-Pyr are considerably higher than those for the analogous mixture containing Bu-azo-5-Pyr. In addition, the entropy change associated with the clearing transition for the equimolar mixture containing Bu-azo-6-Pyr is significantly higher than that for the analogous mixture containing Bu-azo-5-Pyr. These observations strongly suggest the formation of a supramolecular dimeric liquid crystal. For the Bu-azo-6-Pyr-based system the specific molecular interaction between the pyridyl and acid fragments has not only strongly enhanced the liquid crystalline behaviour but also increased the degree of molecular ordering.

  报告了 1-(4-吡啶氧基)-5-[4-(4-丁基苯偶氮)苯氧基]戊烷（Bu-azo-5-Pyr）和 1-(4-吡啶氧基)-6-[4-(丁基苯偶氮)苯氧基]己烷（Bu-azo-6-Pyr）与 4-辛氧基苯甲酸的二元混合物的热学特性。这两种体系在整个成分范围内均可混溶；这种混溶性归因于不同物种之间形成了氢键，红外光谱证实了这一观点。Bu-azo-5-Pyr 和 Bu-azo-6-Pyr 不表现出液晶性，但与酸的混合物却表现出更强的液晶特性。特别是，在这两种体系的相图中都出现了共晶 A 行为。含有 Bu-azo-6-Pyr 的混合物的清澈温度大大高于含有 Bu-azo-5-Pyr 的类似混合物。此外，含有 Bu-azo-6-Pyr 的等摩尔混合物与清澈转变相关的熵变也明显高于含有 Bu-azo-5-Pyr 的类似混合物。这些观察结果有力地证明了超分子二聚液晶的形成。对于基于 Bu-azo-6-Pyr 的体系，吡啶基和酸片段之间的特殊分子相互作用不仅大大增强了液晶的性能，而且提高了分子的有序度。