4-hydroxybenzoic acid 2-[1-(2-hydroxylphenyl)ethylidene]hydrazide | 364054-04-6

• 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-hydroxybenzoic acid 2-[1-(2-hydroxylphenyl)ethylidene]hydrazide
• 英文别名: 4-hydroxy-N'-(1-(2-hydroxyphenyl)ethylidene)benzohydrazide；2-hydroxyacetophenone 4-hydroxybenzoic acid hydrazone；4-hydroxy-N-[1-(2-hydroxyphenyl)ethylideneamino]benzamide
• CAS: 364054-04-6
• 化学式: C₁₅H₁₄N₂O₃
• mdl: MFCD01054934
• 分子量: 270.288
• InChiKey: LVGDDYSLMCRYJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,10-菲罗啉 、 copper(II) choride dihydrate 、 4-hydroxybenzoic acid 2-[1-(2-hydroxylphenyl)ethylidene]hydrazide 以 乙醇 为溶剂， 生成 [Cu(2-hydroxyacetophenone 4-hydroxybenzoic acid hydrazone-2H)(1,10-phenathroline)]
  参考文献：
  名称：

  2-羟基苯乙酮4-羟基苯甲酸和杂环碱的铜（II）三元配合物的光谱表征，X射线结构和生物学研究

  摘要：

  铜的两个新的杂环碱加合物（II）通式CuLB，其中L是2-羟基苯乙酮4-羟基苯甲酸腙二价阴离子，B是杂环碱基，2,2的络合物'联吡啶（联吡啶）或1，已合成10-菲咯啉（phen），并通过不同的物理化学方法对其进行了表征。在DMF溶液中的摩尔电导率测量值表明了两种络合物的非电解质性质。电子和红外光谱数据表明，该配合物具有方形金字塔形几何结构和一个二元三齿配体L 2-和一个双齿杂环基。通过酰肼部分的去质子化的羟基，偶氮甲碱氮和氧进行配位。室温下的磁化率值与单体铜（II）物种的仅自旋值一致。所有化合物的EPR研究给出了轴向光谱。模拟EPR光谱给出了每种化合物的g和A最佳值。的克数值表示未配对电子所在在d X 2 - ÿ 2轨道。通过单晶X射线衍射法确定CuLphen的晶体和分子结构。对抗菌活性的研究表明，该化合物对革兰氏阴性细菌具有中等活性。

  DOI：

  10.1016/j.poly.2003.11.005
• 作为产物：
  描述：

  对羟基苯甲酸 在 hydrazine hydrate 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 为溶剂， 生成 4-hydroxybenzoic acid 2-[1-(2-hydroxylphenyl)ethylidene]hydrazide
  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 and spectral characterization of ternary complexes of oxovanadium(IV) containing some acid hydrazones and 2,2′-bipyridine
  作者：P.B. Sreeja、M.R.Prathapachandra Kurup

  DOI：10.1016/j.saa.2004.04.001

  日期：2005.1

  An interesting series of heterocyclic base adducts of oxovanadium(IV) complexes have been synthesized by the reaction of vanadium(IV) oxide acetylacetonate with some hydrazones (H(2)L) in the presence of a heterocyclic base 2,2'-bipyridine. The compounds were characterized by analytical and different physico-chemical techniques like IR, electron paramagnetic resonance (EPR) and UV-Vis spectral studies

  氧钒（IV）配合物的一系列有趣的杂环碱加合物已通过在杂环碱2,2'-联吡啶的存在下，氧化钒（IV）乙酰丙酮化物与某些（H（2）L）的反应合成。这些化合物通过分析和不同的物理化学技术（例如IR，电子顺磁共振（EPR）和UV-Vis光谱研究和磁性研究）进行表征。EPR光谱表明自由电子在d（xy）轨道中。在所有配合物中，氧钒（IV）周围的配位几何是八面体，具有一个二元三齿配体L（2-）和一个二齿杂环碱基。红外光谱表明配位反应是通过甲亚胺氮和酰肼部分的烯醇氧和酚盐的氧发生的。the的吡啶氮原子 H（2）L（2）和H（2）L（4）不参与协调。摩尔电导率表明所有配合物均为非电解质。分配了所有电子转换。所有化合物都是顺磁性的。所有化合物的EPR研究表明轴向对称。计算出的键合参数表明，面内sigma键合比面内pi键更共价。
• AlCl3·6H2O-catalyzed Schiff-base reaction between aryl ketones and aromatic acylhydrazines/hydrazines in water
  作者：Zhi Xiang Zhao、Ting Li、Li Ping Cheng、Meng Li、Zhi Jian Zhong、Wan Pang

  DOI：10.1007/s00706-019-02488-2

  日期：2019.10

  types of Schiff-bases. In this study, a green synthesis of aromatic hydrazones and acylhydrazones via Schiff-base reaction of aryl ketones and aromatic acylhydrazines/hydrazines had been reported. In the synthesis, water was used as solvent and AlCl3·6H2O was used as catalyst. The reaction is simple, highly efficient, and eco-friendly. Graphic abstract

  摘要希夫碱在分析，生物医学以及材料科学领域具有重要的应用。dra和酰基hydr是席夫碱的两种代表性类型。在该研究中，已经报道了通过芳基酮和芳族酰基肼/肼的席夫碱反应绿色合成芳族肼和酰基hydr。在合成中，水用作溶剂，AlCl 3 ·6H 2 O用作催化剂。该反应简单，高效且环保。 图形摘要