N'-(1-(2-hydroxy-5-methoxyphenyl)ethylidene)benzohydrazide | 935732-58-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-(1-(2-hydroxy-5-methoxyphenyl)ethylidene)benzohydrazide
• 英文别名: 2-hydroxy-5-methoxyacetophenone benzoylhydrazone；N-[1-(2-hydroxy-5-methoxyphenyl)ethylideneamino]benzamide
• CAS: 935732-58-4
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: JEDNCNPMHWKIFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis(acetylacetonate)oxovanadium 、 N'-(1-(2-hydroxy-5-methoxyphenyl)ethylidene)benzohydrazide 、 氧气 以 丙酮 为溶剂， 以86.83%的产率得到[V2O3(2-hydroxy-5-methoxylacetophenone benzoylhydrazone(-2H))2]
  参考文献：
  名称：

  [OV（μ-O）VO] 4+核的双核肼基钒（V）配合物的合成，结构和溶液化学

  摘要：

  双核trioxidic [{VOL} 2 μ-O]（1 - 4）复合物从[V的反应合成IV O（ACAC）2 ]与H的等摩尔量的2 L [ħ 2 L是腙的通用缩写苯甲酰肼与2-羟基苯乙酮或其对位取代衍生物的缩合反应得到的配体（H 2 L 1-4）在丙酮或CH 2 Cl 2或乙腈中。这些V 2 O 3 L 2配合物也是从VOSO 4与H的反应中获得的。在甲醇水溶液（50％V / V）中存在两个当量乙酸钠的情况下，也来自[V IV O（L）（bipy / phen）]络合物在CH 2 Cl 2溶液中的分解，生成2 L乙酸。[V IV O（acac）2 ]分别与H 2 L 2和H 2 L 4反应，得到具有C 2 / c空间群的2和4的黑色单斜晶体。在丙酮中，其中各个配体经完全去质子化的烯醇形式经子午键合到钒上。V–O键的长度遵循以下顺序：V–O（氧代）

  DOI：

  10.1016/j.poly.2008.03.018
• 作为产物：
  描述：

  苯甲酸甲酯 在 hydrazine hydrate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 N'-(1-(2-hydroxy-5-methoxyphenyl)ethylidene)benzohydrazide
  参考文献：
  名称：

  Acetophenone benzoylhydrazones as antioxidant agents: Synthesis, in vitro evaluation and structure-activity relationship studies

  摘要：

  Acetophenone and its analogues are naturally-occurring compounds found in many foods and plants. In this study, a series of acetophenone benzoylhydrazones 5a-o were designed and synthesized as new potential antioxidant agents. Designed molecules contain hydrazone and phenolic hydroxyl moieties which possibly contribute to antioxidant activity. The antioxidant properties of compounds 5a-o in terms of reducing ability and radical-scavenging activity were assessed by using FRAP and DPPH tests, respectively. While the unsubstituted compound 5a had the superior capacity in the FRAP assay, the 2,4-dihydroxyacetophenone analogue 5g was the most potent radical scavenger in the DPPH method. The antioxidant potential of representative compounds 5a and 5g was further confirmed by TEAC and ORAC assays. Cell viability assays revealed that while the promising compounds 5a and 5g had no significant toxicity against HepG2 and NIH3T3 cells, they potently protected HepG2 cells against H2O2 -induced oxidative damage at low concentrations. Furthermore, spectroscopic studies with different biometals demonstrated that 5g was able to interact with Cu2+ to form a 1:1 complex.

  DOI：

  10.1016/j.foodchem.2018.06.083

文献信息

• Synthesis, structure and solution chemistry of dioxidovanadium(V) complexes with a family of hydrazone ligands. Evidence of formation of centrosymmetric dimers via H-bonds in the solid state
  作者：Bipul Mondal、Michael G.B. Drew、Tapas Ghosh

  DOI：10.1016/j.ica.2010.03.053

  日期：2010.6

  formation of centrosymmetric dimers while the complex 12 (containing only one hydrogen atom in the cationic part) exhibits normal H-bonding. The nature of the H-bonds in each of the four centrosymmetric dimeric complexes is different. These complexes have potential catalytic activity in the aerial oxidation of l -ascorbic acid and are converted into the [VO(L)(hq)] complexes containing VO 3+ motif on reaction

  [V IV O（acac）2]与三齿ONO供体配体（H 2 L 1-4，通用缩写H 2 L；由苯甲酰肼与2-羟基苯乙酮及其5的缩合反应而得）的甲醇溶液反应取代的衍生物）在比吡啶强碱性的中性单齿烷基胺碱（例如乙胺，二乙胺，三乙胺和哌啶）的存在下（一般缩写B）产生BH + [VO 2 L]-（1-16）配合物。这16种络合物中的5种在结构上具有特征，表明钒在扭曲的方形锥体环境中存在于分子的阴离子部分[VO 2 L]-中。配合物5、6、15和16在其阳离子部分包含两个与胺N原子相连的H原子（例如，二乙基铵和哌啶鎓离子）与相邻分子发生H键合，导致形成中心对称的二聚体，而配合物12（在阳离子部分仅含一个氢原子）表现出正常的H键合。四个中心对称二聚体复合物中的每一个的H键性质不同。这些配合物在1-抗坏血酸的空中氧化中具有潜在的催化活性，并在与等摩尔量的8-羟基喹啉（Hhq）在甲醇中反应时转化为含有VO
• Synthesis, structure and solution chemistry of quaternary oxovanadium(V) complexes incorporating hydrazone ligands
  作者：Bipul Mondal、Michael G.B. Drew、Tapas Ghosh

  DOI：10.1016/j.ica.2009.02.043

  日期：2009.7

  [VIVO(acac)(2)] reacts with an equimolar amount of benzoyl hydrazone of 2-hydroxyacetophenone (H2L1) or 5-chloro-2-hydroxyacetophenone (H2L2) in the presence of excess pyridine (py) in methanol to produce the quaternary [(VO)-O-V(L-1)(OCH3)(py)] (1) and [(VO)-O-V(L-2)(OCH3)(py)] (2) complexes, respectively, while under similar condition, the benzoyl hydrazones of 2-hydroxy-5-methylacetophenone (H2L3) and 2-hydroxy-5-methoxyacetophenone (H2L4) afforded only the methoxy bridged dimeric [(VO)-O-V(L-3/L-4)(OCH3)](2) complexes. The X-ray structural analysis of 1 and 2 indicates that the geometry around the metal is distorted octahedral where the three equatorial positions are occupied by the phenolate-O, enolate-O and the imine-N of the fully deprotonated hydrazone ligand in its enolic form and the fourth one by a methoxide-O atom. An oxo-O and a pyridine-N atom occupy two axial positions. Quaternary complexes exhibit one quasi-reversible one-electron reduction peak near 0.25 V versus SCE in CH2Cl2 and they decompose appreciably to the corresponding methoxy bridged dimeric complex in CDCl3 solution as indicated by their H-1 NMR spectra. These quaternary VO3+ complexes are converted to the corresponding V2O34+-complexes simply on refluxing them in acetone and to the VO2+-complexes on reaction with KOH in methanol. An equimolar amount of 8-hydroxyquinoline (Hhq) converts these quaternary complexes to the ternary [(VO)-O-V(L)(hq)] complexes in CHCl3. (C) 2009 Elsevier B. V. All rights reserved.
• Chemistry of mixed-ligand methoxy bonded oxidovanadium(V) complexes with a family of hydrazone ligands containing VO3+ core and their substituent controlled methoxy-bridged dimeric forms
  作者：Bipul Mondal、Michael G.B. Drew、Rahul Banerjee、Tapas Ghosh

  DOI：10.1016/j.poly.2008.07.004

  日期：2008.10

  [(VO)-O-IV(acac)(2)] reacts with an equimolar amount of benzoyl hydrazones of 2-hydroxyacetophenone (H2L1), 2-hydroxy-5-methylacetophenone (H2L2) and 5-chloro-2-hydroxyacetophenone (H2L4) in methanol to afford the penta-coordinated mixed-ligand methoxy bonded oxidovanadium(V) complexes [(VO)-O-V(L-1)-(OCHA(3))](1). [(VO)-O-V(L-2)(OCH3)](2), and [(VO)-O-V(L-4)(OCH3)](4), respectively, whereas, the similar reaction with the benzoyl hydrazone of 2-hydroxy-5-methoxyacetophenone (H2L3) producing only the hexa-coordinated dimethoxy-bridged dimeric complex [(VO)-O-V(L-3)(OCH3)](2) (3A). Similar type of hexa-coordinated dimeric analogue of 1 i.e., [(VO)-O-V(L-1)(OCH3)](2) (1A) was obtained from the reaction of [(VO)-O-IV(acac)(2)] with the equimolar amount of H2L1 in presence of half equivalent 4,4'-bipyridine in methanol while the decomposition of [(VO)-O-IV(L-2)(bipy)] complex in methanol afforded the dimeric analogue of 2 i.e., [(VO)-O-V(L-2)(OCH3)](2) (2A). All these dimeric complexes 1A-3A react with an excess amount of imidazole in methanol producing the respective monomeric complex. The X-ray structural analysis of 1-3 and their dimeric analogues 1A-3A indicates that the geometry around the vanadium center in the monomeric form is distorted square-pyramidal while that of their respective dimeric forms is distorted octahedral, where the ligands are bonded to vanadium meridionally in their fully deprotonated enol forms. Due to the formation of bridge, the V-O(methoxy) bond in the dimeric complexes is lengthened to such an extent that it becomes equal in length with the V-O(phenolate) bond in 3A and even longer in 1A and 2A, which is unprecedented. The H-1 NMR spectra of the complexes 1A-3A in CDCl3 solution, indicates that these dimeric complexes are converted appreciably into their respective monomeric form. Complexes are electro-active displaying one quasi-reversible reduction peak near +0.25 V versus SCE in CH2Cl2 solution. The E-1/2 values of the complexes show linear relationship with the Hammett parameter (sigma) of the substituents. All these VO3+-complexes are converted to the corresponding complexes with V2O34+ motif simply on refluxing them in acetone and to the complexes with VO2+ motif on reaction with 2 KOH in methanol. (C) 2008 Elsevier Ltd. All rights reserved.
• Ghosh, Tapas; Mondal, Bipul, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 2008, vol. 47, # 3, p. 361 - 368
  作者：Ghosh, Tapas、Mondal, Bipul

  DOI：——

  日期：——