4-nitro-o-quaterphenyl | 78487-00-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-nitro-o-quaterphenyl
• 英文别名: 1-[2-(4-nitrophenyl)phenyl]-2-phenylbenzene
• CAS: 78487-00-0
• 化学式: C₂₄H₁₇NO₂
• 分子量: 351.404
• InChiKey: HFBFLUXJZAUFPD-UHFFFAOYSA-N

物化性质

• 熔点：
  135.5-137 °C(Solv: cyclohexane (110-82-7))
• 沸点：
  472.1±14.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-nitro-o-quaterphenyl 以98%的产率得到
  参考文献：
  名称：

  OZASA SHIGERU; FUJIOKA YASUHIRO; TSUKADA MACHIYO; IBUKI EIICHI, CHEM. AND PHARM. BULL., 1981, 29, NO 2, 344-355

  摘要：

  DOI：
• 作为产物：
  描述：

  邻四联苯 生成 4-nitro-o-quaterphenyl
  参考文献：
  名称：

  FUJIOKA, YASUHIRO;OZASA, SHIGERU;SATO, KAZUMI;IBUKI, EIICHI, CHEM. AND PHARM. BULL., 1984, 33, N 1, 22-29

  摘要：

  DOI：

文献信息

• Syntheses and physical properties of several octiphenyls containing mixed linkages.
  作者：SHIGERU OZASA、YASUHIRO FUJIOKA、MACHIYO TSUKADA、EIICHI IBUKI

  DOI：10.1248/cpb.29.344

  日期：——

  Eight new linear octiphenyls containing two or three kinds of linkage were synthesized by the Ullmann homo-coupling reaction of iodoquaterphenyl. Among them, five compounds were alternatively synthesized by the Kharash-type Grignard cross-coupling of biphenylylmagnesium bromide and diiodoquaterphenyl or of terphenylylmagnesium iodide and diiodoquaterphenyl in the presence of bis (acetylacetonato) nickel (II). Spectral studies proved that the octiphenyls thus prepared displayed highly characteristic infrared, ultraviolet, and nuclear magnetic resonance spectra. Empirical Huckel molecular orbital calculations of the longest wavelength absorption bands of the octiphenyls were also performed. The calculated and observed wavelengths were in rather good agreement, except for the cases of two compounds.

  通过碘四联苯的Ullmann同系偶联反应合成了8个新型线性八联苯，包含2种或3种连接方式。其中5个化合物是通过双(乙酰丙酮)镍(II)催化的二碘四联苯和联苯基溴化镁或三联苯基碘化镁的Kharash型Grignard交叉偶联反应替代合成的。光谱研究表明，这些合成的八联苯显示出非常有特征的红外、紫外和核磁共振光谱。同时对八联苯最长波长吸收带的实验性Huckel分子轨道计算也进行了研究，除了两种化合物外，计算得到的波长与观测值相当吻合。
• ortho-Phenylene oligomers with terminal push–pull substitution
  作者：Jian He、Sanyo M. Mathew、Sarah D. Cornett、Stephan C. Grundy、C. Scott Hartley

  DOI：10.1039/c2ob07146k

  日期：——

  ortho-Phenylenes are an emerging class of helical oligomers and polymers. We have synthesized a series of push–pull-substituted o-phenylene oligomers (dimethylamino/nitro) up to the octamer. Conformational analysis of the hexamer using a combination of low-temperature NMR spectroscopy and ab initio predictions of 1H NMR chemical shifts indicates that, like other o-phenylenes, they exist as compact helices in solution. However, the substituents are found to have a significant effect on their conformational behavior: the nitro-functionalized terminus is 3-fold more likely to twist out of the helix. Protonation of the dimethylamino group favors the helical conformer. UV/vis spectroscopy indicates that the direct charge-transfer interaction between the push–pull substituents attenuates quickly compared to other conjugated systems, with no significant charge-transfer band for oligomers longer than the trimer. On protonation of the dimethylamino group, significant bathochromic shifts with increasing oligomer length are observed: the effective conjugation length is 9 repeat units, more than twice that of the parent oligomer. This behavior may be rationalized through examination of the frontier molecular orbitals of these compounds, which exhibit greater delocalization after protonation, as shown by DFT calculations.

  邻苯基是一类新兴的螺旋低聚物和聚合物。我们合成了一系列推拉取代的邻苯基低聚物（二甲基氨基/硝基），直至八聚体。利用低温核磁共振光谱和 1H NMR 化学位移的 ab initio 预测相结合的方法对六聚体进行的构象分析表明，与其他邻苯基一样，它们在溶液中以紧凑的螺旋形式存在。然而，研究发现取代基对它们的构象行为有显著影响：硝基官能化的末端从螺旋中扭曲出来的可能性要高出 3 倍。二甲基氨基的质子化有利于螺旋构象。紫外/可见光谱显示，与其他共轭体系相比，推拉取代基之间的直接电荷转移相互作用迅速减弱，对于长于三聚体的低聚物来说，没有明显的电荷转移带。当二甲基氨基发生质子化时，随着低聚物长度的增加，会出现明显的浴色偏移：有效共轭长度为 9 个重复单元，是母体低聚物的两倍多。这种行为可以通过研究这些化合物的前沿分子轨道得到合理解释，正如 DFT 计算所显示的那样，质子化后，前沿分子轨道表现出更大的脱位。
• Fujioka, Yasuhiro; Ozasa, Shigeru; Sato, Kazumi, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 1, p. 22 - 29
  作者：Fujioka, Yasuhiro、Ozasa, Shigeru、Sato, Kazumi、Ibuki, Eiichi

  DOI：——

  日期：——