1-(4-fluorophenyl)-1-phenylhydrazine | 2711-99-1

• 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: 1-(4-fluorophenyl)-1-phenylhydrazine
• 英文别名: N-Phenyl-N-(4-fluor-phenyl)-hydrazin；1-(4-Fluorophenyl)-1-phenylhydrazine
• CAS: 2711-99-1
• 化学式: C₁₂H₁₁FN₂
• 分子量: 202.231
• InChiKey: IKELAHQYZUSFCW-UHFFFAOYSA-N

物化性质

• 沸点：
  167 °C(Press: 1 Torr)
• 密度：
  1.222±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-fluorophenyl)-1-phenylhydrazine 在 lead dioxide 作用下， 生成 N'-(4-fluoro-phenyl)-N'-phenyl-N-picryl-hydrazine
  参考文献：
  名称：

  Matewosjan et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 858,863; engl. Ausg. S. 843, 847

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲苯亚磺酸苯酯 、 4-氟苯肼盐酸盐 在 potassium phosphate 、 palladium(II) trifluoroacetate 、 2-(2-(dicyclohexylphosphino)-4,5-dimethoxyphenyl)-1-methyl-1H-indole 、 苯硼酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.01h， 以90%的产率得到1-(4-fluorophenyl)-1-phenylhydrazine
  参考文献：
  名称：

  钯催化芳基甲苯磺酸与芳基甲苯磺酸酯的单芳基化。

  摘要：

  已开发了钯催化的芳基肼与芳基甲苯磺酸酯之间的C–N键偶联反应，可轻松合成不对称的N，N-二芳基肼。利用与新开发的膦配体L1关联的Pd（TFA）2催化剂体系，芳基肼的单芳基化反应顺利进行，以良好的产率（高达95％）提供了具有良好官能团相容性的所需产品。该方法提供了从简单且容易获得的偶联组分中获得结构多样的N，N-二芳基肼的替代合成途径。

  DOI：

  10.1021/acs.joc.0c01599

文献信息

• Zirconium-Catalyzed Multistep Reaction of Hydrazines with Alkynes: A Non-Fischer-Type Pathway to Indoles
  作者：Thorsten Gehrmann、Julio Lloret Fillol、Solveig A. Scholl、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1002/anie.201101070

  日期：2011.6.14

  Dominos at zirconium: A cascade of N–N and C–H scissions and C–C and C–N coupling steps in the coordination sphere of zirconium directly converts alkynes and hydrazines into indoles. The reaction pathway differs fundamentally from that of the Fischer indole synthesis.

  锆中的多米诺骨牌：锆的配位领域中的N–N和C–H剪接级联以及C–C和C–N偶联步骤直接将炔烃和肼转化为吲哚。该反应途径与费歇尔吲哚合成的反应途径根本不同。
• CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：Samsung Electronics Co., Ltd

  公开号：EP2977378A1

  公开（公告）日：2016-01-27

  Claimed are condensed cyclic compound of Formulae 1A to 1D and their use in organic electroluminescent light-emitting devices (OLED).

  权利要求 1A 至 1D 的缩合环状化合物及其在有机电致发光器件（OLED）中的用途。
• Titanium-Catalyzed Hydrohydrazination of Carbodiimides
  作者：Peter D. Schweizer、Hubert Wadepohl、Lutz H. Gade

  DOI：10.1021/om400323p

  日期：2013.7.8

  Hydrazinediido complexes of the type [Cp*Ti-(NxylN)(NNR2)(L)] (R = Ph, Me; Ar, fluorene, L = (BuNH2)-Bu-t, Py; 3a-e) have been synthesized and used as catalysts for the hydrohydrazination of a series of carbodiimides, yielding aminoguanidines or fluoreneiminoguanidines. The highest yields were obtained for diarylhydrazines and fluorenone 5 hydrazone at temperatures between 80 and 105 degrees C. Stoichiometric reactions of hydraz inediido complexes with (PrNCNPr)-Pr-i-Pr-i led to an equilibrium with the resulting [2 + 2] cydoadducts 4a-f, which were characterized by H-1, C-13, and N-15 NMR spectroscopy as well as X-ray diffraction. The proposed mechanism, which is closely related to that previously established for the hydrohydrazination of alkynes and allenes, was found to be consistent with the results of a kinetic study. The dynamic structures of aminoguanidines and fluoreneiminoguanidines were characterized by NMR spectroscopy, and the minimum configurations were foud to be stabilized by intramolecular hydrogen bonding.