4-(1-hydrazono-ethyl)-benzonitrile | 93480-05-8

• 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-(1-hydrazono-ethyl)-benzonitrile
• 英文别名: 4-(1-Hydrazono-aethyl)-benzoesaeure-nitril；4-(1-Hydrazono-aethyl)-benzonitril；Benzonitrile, 4-(1-hydrazonoethyl)-；4-ethanehydrazonoylbenzonitrile
• CAS: 93480-05-8
• 化学式: C₉H₉N₃
• 分子量: 159.191
• InChiKey: HFJZXQZKSPYGIZ-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  62.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘苯二乙酸 、 4-(1-hydrazono-ethyl)-benzonitrile 以90%的产率得到4-(1-acetoxy-ethyl)-benzonitrile
  参考文献：
  名称：

  Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions

  摘要：

  含有吸电子、还原敏感取代基的芳香腙1与MTIB反应，可高效地得到相应的甲苯磺酸酯2。当甲苯磺酸酯具有特别高的反应活性时，则会分离得到热力学上更稳定的方式形成的甲醚3。类似地，与DAIB反应可高效地得到乙酸酯4。二烷基腙则生成烯烃产物（例如7和8）。(+)-樟脑腙1k与MTIB或DAIB反应，会同时生成荻烯12（主要产物）和三环烯11（次要产物），表明在这些氧化反应中，卡宾路径可能用于形成一部分反应产物。

  DOI：

  10.1055/s-1997-702
• 作为产物：
  描述：

  对氰基苯乙酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 以65%的产率得到4-(1-hydrazono-ethyl)-benzonitrile
  参考文献：
  名称：

  Synthesis, Characterisation, and Phase Behaviour of Some Azines with Potential Optical Nonlinearities of Second Order

  摘要：

  Some azines with potential nonlinear optical properties of the second order have been synthesised by condensation of the appropriate hydrazones and aldehydes. The compounds have been chemically functionalised to allow their use in the synthesis of polymers containing the azine groups as side chain pendants. The characterisation of the phase behaviour, performed by DSC, X-ray diffraction and polarising microscopy methods, shows that most of the compounds exhibit enantiotropic liquid crystalline properties. Some peculiar features concerning solid state polymorphism have also been investigated.

  DOI：

  10.1080/10587259608034066

文献信息

• Structural and theoretical analysis of some mesogenic azines containing strong electron donor–acceptor groups
  作者：Roberto Centore、Carmine Garzillo

  DOI：10.1039/a604300c

  日期：——

  A structural and theoretical analysis of some mesogenic bis(phenylene)azines containing a methyl group on the azine system and strong electron donor–acceptor groups on the phenylene rings is reported. Starting from the X-ray molecular structures and with the support of semiempirical quantum mechanical calculations, the structural and conformational properties of the azines are analysed and compared with recent literature data on similar acetophenone azines. Some geometrical and electronic data of the molecules are also calculated and discussed in the paper, which may be useful for a better understanding of the mesophasic behaviour of the compounds.

  报告对一些介原双(亚苯基)叠氮进行了结构和理论分析，这些叠氮在叠氮系统上含有一个甲基，在亚苯基环上含有强电子供体和受体基团。从 X 射线分子结构出发，在半经验量子力学计算的支持下，分析了这些偶氮的结构和构象特性，并与最近关于类似苯乙酮偶氮的文献数据进行了比较。文中还计算并讨论了分子的一些几何和电子数据，这些数据可能有助于更好地理解这些化合物的介相行为。
• 166. The preparation of some stilbene derivatives. Part III
  作者：H. J. Barber、R. Slack

  DOI：10.1039/jr9440000612

  日期：——
• Synthesis, Characterisation, and Phase Behaviour of Some Azines with Potential Optical Nonlinearities of Second Order
  作者：R. Centore、B. Panunzi、A. Roviello、A. Sirigu、P. Villano

  DOI：10.1080/10587259608034066

  日期：1996.1

  Some azines with potential nonlinear optical properties of the second order have been synthesised by condensation of the appropriate hydrazones and aldehydes. The compounds have been chemically functionalised to allow their use in the synthesis of polymers containing the azine groups as side chain pendants. The characterisation of the phase behaviour, performed by DSC, X-ray diffraction and polarising microscopy methods, shows that most of the compounds exhibit enantiotropic liquid crystalline properties. Some peculiar features concerning solid state polymorphism have also been investigated.
• Reaction of Hydrazones with Methoxy(tosyloxy)iodobenzene (MTIB): Tosylate Formation under Oxidative Conditions
  作者：Christopher Ramsden、Helen Rose

  DOI：10.1055/s-1997-702

  日期：——

  Treatment of aromatic hydrazones 1 containing electron-withdrawing, reduction sensitive substituents with MTIB gives the corresponding tosylates 2 in high yield. When the tosylate is particularly reactive the thermodynamically more stable methyl ether 3 is isolated. Analogous reactions with DAIB give acetates 4 in high yield. Dialkyl hydrazones give olefinic products (e.g. 7 and 8). (+)-Camphor hydrazone 1k with either MTIB or DAIB gives both camphene 12 (major product) and tricyclene 11 (minor product) suggesting that a carbene pathway accounts for some of the material formed in these oxidations.

  含有吸电子、还原敏感取代基的芳香腙1与MTIB反应，可高效地得到相应的甲苯磺酸酯2。当甲苯磺酸酯具有特别高的反应活性时，则会分离得到热力学上更稳定的方式形成的甲醚3。类似地，与DAIB反应可高效地得到乙酸酯4。二烷基腙则生成烯烃产物（例如7和8）。(+)-樟脑腙1k与MTIB或DAIB反应，会同时生成荻烯12（主要产物）和三环烯11（次要产物），表明在这些氧化反应中，卡宾路径可能用于形成一部分反应产物。