2-oxopropanal (4-methylphenyl)hydrazone | 18804-66-5

• 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: 2-oxopropanal (4-methylphenyl)hydrazone
• 英文别名: 1-[2-(4-methylphenyl)hydrazinylidene]propan-2-one；1-(2-(p-tolyl)hydrazono)propan-2-one；Methylglyoxal-p-tolylhydrazon；1-(p-tolyl-hydrazono)-propan-2-one；β-Oxo-α-p-toolylhydrazono-propan；pyruvaldehyde-1-p-tolylhydrazone；Methylglyoxal-ω-p-tolylhydazon；Pyruvaldehyd-1-p-tolylhydrazon；Acetonyliden-p-tolylhydrazin；1-[(4-Methylphenyl)hydrazinylidene]propan-2-one；1-[(4-methylphenyl)hydrazinylidene]propan-2-one
• CAS: 18804-66-5
• 化学式: C₁₀H₁₂N₂O
• 分子量: 176.218
• InChiKey: UFVKXRCBBFGXKO-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C(Solv: toluene (108-88-3))
• 沸点：
  284.0±33.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  41.46
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-oxopropanal (4-methylphenyl)hydrazone 在 一水合肼 作用下， 生成 bis-(p-tolylhydrazono-isopropylidene)-hydrazine
  参考文献：
  名称：

  Henseke; Binte, Justus Liebigs Annalen der Chemie, 1958, vol. 612, p. 205,212

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl 3-oxo-2-(p-tolylhydrazono)butanoate 在 sodium hydroxide 作用下， 生成 2-oxopropanal (4-methylphenyl)hydrazone
  参考文献：
  名称：

  v. Richter; Muenzer, Chemische Berichte, 1884, vol. 17, p. 1927

  摘要：

  DOI：

文献信息

• Behaviour of Arylazo tert-Butyl Sulfides with Ketone Enolates. Competition between SRN1 α-arylation and Azocoupling Reactions.
  作者：Carlo Dell'Erba、Marino Novi、Giovanni Petrillo、Cinzia Tavani

  DOI：10.1016/s0040-4020(01)88144-8

  日期：——

  room temperature, with potassium acetone enolate to give good yields of 1-aryl-2-propanones via spontaneous SRN1 dark reactions, α-Phenylation of pinacolone and acetophenone enolates by 1a likewise occurs in excellent yields. In agreement with the involvement of an electron-transfer catalyzed chain process, the reaction of the 4-bromo derivative 1n with pinacolone enolate gives mainly the bis-substitution

  （Z）-芳基偶氮叔丁基硫化物1a-i在DMSO中和室温下与丙酮烯醇钾反应，通过自发的S RN 1暗反应，频哪酮的α-苯甲酰化反应生成1-芳基-2-丙烷的良好收率苯乙酮烯醇化1a的收率也很高。与电子转移催化链过程的参与相一致，4-溴衍生物1n与频哪酮烯醇酸酯的反应主要产生双取代产物13。在偶氮硫化物1j–m中，芳基化途径与碱基诱导的硫醇消除竞争，最终取决于偶氮硫化物的结构而导致吲唑8或11和/或2-氧代丙醛芳基腙9，10或12。
• New Multifunctional Agents for Potential Alzheimer’s Disease Treatment Based on Tacrine Conjugates with 2-Arylhydrazinylidene-1,3-Diketones
  作者：Natalia A. Elkina、Maria V. Grishchenko、Evgeny V. Shchegolkov、Galina F. Makhaeva、Nadezhda V. Kovaleva、Elena V. Rudakova、Natalia P. Boltneva、Sofya V. Lushchekina、Tatiana Y. Astakhova、Eugene V. Radchenko、Vladimir A. Palyulin、Ekaterina F. Zhilina、Anastasiya N. Perminova、Luka S. Lapshin、Yanina V. Burgart、Victor I. Saloutin、Rudy J. Richardson

  DOI：10.3390/biom12111551

  日期：——

  development of new effective therapeutic agents for AD is one of the most urgent and challenging tasks. To address this need, we used an aminoalkylene linker to combine the well-known anticholinesterase drug tacrine with antioxidant 2-tolylhydrazinylidene-1,3-diketones to create 3 groups of hybrid compounds as new multifunctional agents with the potential for AD treatment. Lead compounds of the new conjugates

  阿尔茨海默病 (AD) 被认为是一种现代流行病，因为它在全球范围内的患病率不断上升，并产生严重的医学社会后果，包括治疗和患者护理的经济负担。开发新的有效治疗AD的药物是最紧迫和最具挑战性的任务之一。为了满足这一需求，我们使用氨基亚烷基连接体将著名的抗胆碱酯酶药物他克林与抗氧化剂 2-甲苯基亚肼基-1,3-二酮结合起来，创建了 3 组杂合化合物，作为具有 AD 治疗潜力的新型多功能药物。新缀合物的先导化合物可有效抑制乙酰胆碱酯酶（AChE，IC 50 0.24–0.34 µM）和丁酰胆碱酯酶（BChE，IC 50 0.036–0.0745 µM），对脱靶羧酸酯酶的抑制较弱。抗AChE活性随着亚烷基间隔基的延长而增加，这与分子对接一致，这表明化合物与AChE的催化活性位点和外周阴离子位点（PAS）结合，这与混合型可逆抑制一致。 PAS 结合以及有效的丙啶置换表明该杂交体具有阻断 AChE 诱导的
• Shmelev, L. V.; Lipunova, G. N.; Sulim, O. P., Journal of general chemistry of the USSR, 1986, vol. 56, p. 2114 - 2121
  作者：Shmelev, L. V.、Lipunova, G. N.、Sulim, O. P.、Bednyagina, N. P.

  DOI：——

  日期：——
• Weygand et al., Chemische Berichte, 1955, vol. 88, p. 487,497
  作者：Weygand et al.

  DOI：——

  日期：——
• 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.