1,1':4',1'':3'',1''':4''',1''''-quinquephenyl | 13476-68-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 1,1':4',1'':3'',1''':4''',1''''-quinquephenyl
• 英文别名: 1,3-bisphenyl-4-yl-benzene；4,4''-diphenyl-m-terphenyl；1,3-di(biphenyl)benzene；1,3-dibiphenylylbenzene；1,3-dibiphenylbenzene；[1,1';4',1'';3'',1''';4''',1'''']Quinquephenyl；1,3-Bis(4-phenylphenyl)benzene
• CAS: 13476-68-1
• 化学式: C₃₀H₂₂
• 分子量: 382.505
• InChiKey: DTSKGGTWHPYABJ-UHFFFAOYSA-N

物化性质

• 熔点：
  264-266 °C
• 沸点：
  600.9±35.0 °C(Predicted)
• 密度：
  1.091±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2,6-二溴苯胺 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 为溶剂， 反应 6.5h， 生成 1,1':4',1'':3'',1''':4''',1''''-quinquephenyl
  参考文献：
  名称：

  A one-pot synthesis of m-terphenyls, via a two-aryne sequence

  摘要：

  DOI：

  10.1021/jo00366a016

文献信息

• Studies of Polyphenyls and Polyphenylenes. II. The Synthesis and Physical Properties of Polyphenyls Containing Para Linkage
  作者：Shigeru Ozasa、Noriko Hatada、Yasuhiro Fujioka、Eiichi Ibuki

  DOI：10.1246/bcsj.53.2610

  日期：1980.9

  information. The HMO calculations of the longest wavelength absorption bands of twenty-four polyphenyls were carried out. A comparison between the calculated and observed wavelengths gave rather good agreement, except in the cases of two compounds. The signals of the proton magnetic resonance spectra of eighteen polyphenyls were assigned tentatively. The correlations between the arrangement of the benzene rings

  通过碘联苯与二碘苯或碘三联苯的 Ullmann 交叉偶联反应合成了 12 种线性多苯，包括五联苯到八联苯。聚苯的紫外光谱研究表明，K 波段以上的位置大约为 260 nm，无论是否存在邻或间亚苯基单元，都可以被认为是连续对亚苯基单元的近似数量的指示。红外研究还表明，815-850 cm-1 区域中强或中波段的位置可能会提供相同的信息。进行了24种聚苯的最长波长吸收带的HMO计算。计算的和观察到的波长之间的比较给出了相当好的一致性，除了两种化合物的情况。初步确定了十八种多苯基的质子磁共振谱信号。讨论了苯环排列与光谱模式之间的相关性。
• Two Efficient Routes to m-Terphenyls from 1,3-Dichlorobenzenes
  作者：Akbar Saednya、Harold Hart

  DOI：10.1055/s-1996-4426

  日期：1996.12

  In the first route 2,6-dichlorophenyllithium (5), prepared by direct lithiation of 1,3-dichlorobenzene, reacted with aryl Grignard reagents to give m-terphenyls in 57-93% yields (Table 1); the methodology was extended to substituted 1,3-dichlorobenzenes (i.e. 8 → 10). Also, reaction of 5 with MgCl2 gave 2,6-dichlorophenylmagnesium chloride which, on warming, produced the self-capture product tetrachloro-m-terphenyl 7 in moderate yield. In the second route, reaction of 1,3-dichlorobenzene with excess of aryllithium in diethyl ether at room temperature gave the corresponding m-terphenyls in 59-94% yields (Table 2). Examples are given in which the aryllithium was prepared by three different routes (ArX+Li, ArX+t-BuLi, ArH+BuLi).

  在第一种方法中，2,6-二氯苯锂（5）是通过 1,3-二氯苯的直接石化作用制备的，它与芳基格氏试剂反应生成间三联苯，产率为 57-93%（表 1）；该方法还可扩展到取代的 1,3-二氯苯（即 8 → 10）。此外，5 与 MgCl2 反应生成 2,6-二氯苯基氯化镁，加热后生成自捕获产物四氯间三联苯 7，收率适中。在第二种方法中，1,3-二氯苯在室温下与过量的芳基锂在二乙醚中反应，得到相应的间三联苯，产率为 59-94%（表 2）。举例说明了通过三种不同途径（ArX+Li、ArX+t-BuLi、ArH+BuLi）制备芳基锂的情况。
• Javelin-, Hockey Stick-, and Boomerang-Shaped Liquid Crystals. Structural Variations on <i>p</i>-Quinquephenyl
  作者：Theo J. Dingemans、N. Sanjeeva Murthy、Edward T. Samulski

  DOI：10.1021/jp010869j

  日期：2001.9.1

  The ramifications of changing molecular geometry in a series of all-aromatic liquid crystals derived from p-quinquephenyl are reported. Substituting heterocyclic rings such as thiophene, oxadiazole, oxazole, or 1,3-phenylene into the p-quinquephenylene core affects molecular shape changes via the substituent's exocyclic bond angle. In general, we found that introducing nonlinearity into molecules depresses the melting transition temperature. The symmetric (boomerang-shaped) molecules, 2,5-bisbiphenyl-4-yl-1,3,4-oxadiazole, 2,5-bisbiphenyl-4-yl-oxazole, and 1,3-bisbiphenyl-4-yl-benzene, melt into isotropic phases showing small monotropic mesophases. By contrast, the asymmetric (hockey stick-shaped) mesogens, 2-terphenyl-4-yl-5-phenyl thiophene and 2-terphenyl-4-yl-5-phenyl-1,3,4-oxadiazole, exhibit more stable enantiotropic liquid crystalline phases. The hockey stick-shaped mesogens exhibit a smectic phase as well as a nematic phase. High-temperature X-ray determination of the smectic layer spacing gives an unambiguous picture of interdigitated, bilayerlike supramolecular architecture in the smectic phase. There are associated changes in the mesogen's electrostatic profile when a heterocycle is introduced into the quinquiphenylene framework (e.g., conjugation is perturbed). Our findings suggest that steric packing considerations dominate the phase preferences (nematic versus smectic phases), However, electronic considerations (conjugation) appear to control the range of mesomorphism in this new family of nonlinear liquid crystals.
• Synthesis of m-Diarylbenzenes
  作者：G. Forrest Woods、Irwin W. Tucker

  DOI：10.1021/ja01190a035

  日期：1948.10
• Ozasa, Shigeru; Fujioka, Yasuhiro; Hashino, Hiromi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 7, p. 2313 - 2320
  作者：Ozasa, Shigeru、Fujioka, Yasuhiro、Hashino, Hiromi、Kimura, Naoko、Ibuki, Eiichi

  DOI：——

  日期：——