1-(2-(4-chlorophenyl)hydrazono)propan-2-one | 18804-72-3

• 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-(2-(4-chlorophenyl)hydrazono)propan-2-one
• 英文别名: ω-Methylglyoxal-(4-chlor-phenylhydrazon)；Methylglyoxal-<4-chlor-phenylhydrazon>；1-[(4-chlorophenyl-hydrazono)]-propan-2-one；1-[(4-Chlorophenyl)hydrazinylidene]propan-2-one
• CAS: 18804-72-3
• 化学式: C₉H₉ClN₂O
• 分子量: 196.636
• InChiKey: KHQINXSCEMFKCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-(4-chlorophenyl)hydrazono)propan-2-one 、 2-((1,3-diphenyl-1H-pyrazol-4-yl)methylene)malononitrile 在 哌啶 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以81%的产率得到6-acetyl-3-amino-2-(4-chlorophenyl)-5-(1,3-diphenyl-1H-pyrazol-4-yl)-2,5-dihydropyridazine-4-carbonitrile
  参考文献：
  名称：

  通过[3 + 3]原子组合轻松合成3-氨基-2,5-二氢哒嗪和4-脱氮杂黄酮类似物：吡嗪并入吡唑基的方法

  摘要：

  制备了芳hydr并使其与吡唑基亚甲基丙二腈衍生物反应，生成在C-5处被吡唑衍生物取代的2,5-二氢哒嗪。通过在邻位使用含有氰基的氮杂胺，可以形成缩合的哒嗪并[1,6- a ]喹唑啉衍生物。合成的哒嗪的后续乙酰化导致嘧啶[4,5– c ]哒嗪化合物的形成，可以将其视为4-脱氮杂黄酮衍生物。所有新化合物均通过不同的光谱工具进行了全面表征，并使用2D-HMBC光谱对2,5-二氢哒嗪进行了结构明确的鉴定

  DOI：

  10.1002/jhet.2606

文献信息

• Synthesis, spectroscopic characterization and biological activity on newly synthesized copper(II) and nickel(II) complexes incorporating bidentate oxygen–nitrogen hydrazone ligands
  作者：Ahmed A. El-Sherif

  DOI：10.1016/j.ica.2009.08.004

  日期：2009.11

  We report the synthesis of the hydrazone ligands, 1-(phenyl-hydrazono)-propan-2-one (PHP), 1-(p-tolylhydrazono)-propan-2-one (THP), 1-[(4- chloro-hydrazono)]-propan-2-one (CHP), and their Ni(II) and Cu(II) metal complexes. The structure of the ligands and their complexes were investigated using elemental analysis, magnetic susceptibility, molar conductance and spectral (IR, UV, and EPR) measurements. IR spectra indicate that the free ligands exist in the hydrazo-ketone rather than azo-enol form in the solid state. Also, the hydrazo-NH exists as hydrogen bonded to the keto-oxygen either as intra or as intermolecular hydrogen bonding. In all the studied complexes, all ligands behave as a neutral bidentate ligands with coordination involving the hydrazone-nitrogen and the keto-oxygen atoms. The magnetic and spectral data indicate a square planar geometry for Cu2+ complexes and an octahedral geometry for Ni2+ complexes. The ligands and their metal chelates have been screened for their antimicrobial activities using the disc diffusion method against the selected bacteria and fungi. They were found to be more active against Gram-positive than Gram-negative bacteria. It may be concluded that the antimicrobial activity of the compounds is related to cell wall structure of bacteria.Protonation constant of (PHP) ligand and stability constants of its Cu2+ and Ni2+ complexes were determined by potentiometric titration method in aqueous solution at ionic strength of 0.1 M sodium nitrate. It has been observed that the hydrazone ligand (PHP) titrated here has one protonation constant. The divalent metal ions Cu2+ and Ni2+ form with (PHP) 1:1 and 1:2 complexes. The insolubility of (THP) and (CHP) ligands in aqueous medium does not permit the determination of their protonation constants and formation constants of the corresponding complexes in aqueous solution. (c) 2009 Elsevier B.V. All rights reserved.
• A novel synthesis of 2-arylhydrazono-6-amino-4-arylbenzene-1,3-dicarbonitriles and their conversion into phthalazines
  作者：Saleh M. Al-Mousawi、Moustafa Sherief Moustafa、Mohamed Hilmy Elnagdi

  DOI：10.1016/j.tetlet.2009.08.037

  日期：2009.11

  Compounds 1a-d react with benzylidenemalononitrile 2 to yield dihydroaminopyridazines 3a-d and, in contrast, compounds 1e,f react with 2 under the same conditions to yield aminobenzenedicarbonitriles 8e,f compound 8e underwent intramolecular cyclization to phthalazine 9e. Compound 10e reacted with 2a to yield 11e. (C) 2009 Elsevier Ltd. All rights reserved.