1,2-bis(2,4-dihydroxybenzaldehyde)hydrazone | 23452-50-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1,2-bis(2,4-dihydroxybenzaldehyde)hydrazone
• 英文别名: 1,2-bis(2,4-dihydroxybenzylidene)hydrazine；bis[2,4-dihydroxybenzaldehyde]hydrazone；bis(2,4-dihydroxybenzylidene)hydrazine；4-hydroxysalicylaldehyde azine；β-resorcylaldazine；2,4-dihydroxybenzaldehyde (2,4-dihydroxybenzylidene)hydrazone；4,4'-(Hydrazine-1,2-diylidenebis(methaneylylidene))bis(benzene-1,3-diol)；4-[[(2,4-dihydroxyphenyl)methylidenehydrazinylidene]methyl]benzene-1,3-diol
• CAS: 23452-50-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: YOAMTCGAMHEGGE-UHFFFAOYSA-N

物化性质

• 熔点：
  352 °C
• 沸点：
  530.5±38.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  106
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2-bis(2,4-dihydroxybenzaldehyde)hydrazone 、 copper diacetate 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 copper(II) 6,6'-(hydrazine-1,2-diylidenebis(methaneylylidene))bis(3-hydroxyphenolate)
  参考文献：
  名称：

  Kapadia, R. N., Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1981, vol. 20, # 5, p. 525 - 526

  摘要：

  DOI：
• 作为产物：
  描述：

  7-羟基香豆素-3-羧酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1,2-bis(2,4-dihydroxybenzaldehyde)hydrazone
  参考文献：
  名称：

  某些Hy和2H-苯并吡喃酮衍生物作为抗肿瘤剂的合成及光谱表征

  摘要：

  一系列新腙，2- ħ -苯并吡喃酮-3-甲酰胺和2- ħ -苯并吡喃酮-3- carbonylthiosemicarbazide衍生物是从烷基7-羟基-2-合成ħ -苯并吡喃酮-3-羧酸乙酯（1A，b）和二溴衍生物（图6a，b）是关键的起始材料。合成的新化合物的结构通过IR，1 H，13 C-NMR，MS和元素分析确定。一些衍生物和N取代的2 H评估了苯并吡喃酮-3-羧酰胺类药物对HepG-2细胞系的抗癌活性。这些化合物中的一些具有良好的细胞毒性。

  DOI：

  10.1002/jhet.3211

文献信息

• Salicylaldehyde Azines as Fluorophores of Aggregation-Induced Emission Enhancement Characteristics
  作者：Weixin Tang、Yu Xiang、Aijun Tong

  DOI：10.1021/jo802631m

  日期：2009.3.6

  salicylaldehyde azine derivatives were found to exhibit interesting aggregation-induced emission enhancement (AIEE) characteristics. In good solvent, all these compounds displayed very weak fluorescence, while strong emission was observed when they were placed in poor solvent. Moreover, the AIEE color of these compounds varied from green to red depending on the substituents on azines. Their in situ

  发现一系列水杨醛嗪衍生物表现出令人感兴趣的聚集诱导的发射增强（AIEE）特征。在良好的溶剂中，所有这些化合物均显示出非常弱的荧光，而当将它们置于不良溶剂中时，则观察到强发射。而且，这些化合物的AIEE颜色取决于绿色，从绿色到红色不等，具体取决于嗪上的取代基。它们的原位形成还有望在肼的荧光感测中潜在的应用。
• A three-dimensional porous metal–organic framework [Fe₂L₃·(DMF)₇·(C₄H₁₀O)_0.5] constructed from triple-helices {L = bis[2,4-dihydroxybenzaldehyde]hydrazone}
  作者：Mo Hong、Guo Dong、Duan Chun-ying、Li Yu-ting、Meng Qing-jin

  DOI：10.1039/b206702a

  日期：——

  A novel 3-D large porous metal–organic framework was achieved from triple metal helices via π–π stacking interactions between the aromatic groups of the helices.

  通过三重金属螺旋的芳香基团之间的ÏÏÏ堆叠相互作用，实现了一种新型的三维多孔金属有机框架。
• Thermal property of an aggregation-induced emission fluorophore that forms metal–ligand complexes with Zn(ClO₄)₂ of salicylaldehyde azine-functionalized polybenzoxazine
  作者：Mohamed Gamal Mohamed、Ruey-Chorng Lin、Jia-Huei Tu、Fang-Hsien Lu、Jin-Long Hong、Kwang-Un Jeong、Chih-Feng Wang、Shiao-Wei Kuo

  DOI：10.1039/c5ra09409g

  日期：——

  A salicylaldehyde azine-functionalized benzoxazine monomer formed zinc ion complexes not only improved the thermal properties but also facilitated ring-opening polymerization.

  一种水杨醛偶氮联苯并噁嗪单体形成了锌离子配合物，不仅提高了热性能，而且促进了开环聚合。
• A highly selective chemosensor for Cu2+ and Al3+ in two different ways based on Salicylaldehyde Schiff
  作者：Chao Gou、Shao-Hui Qin、Hai-Qiang Wu、Yu Wang、Jing Luo、Xiao-Ya Liu

  DOI：10.1016/j.inoche.2011.06.024

  日期：2011.10

  A novel, easily available colorimetric and fluorescent double-sensor 1 based on Salicylaldehyde bis-Schiff has been investigated in this work. The sensor exhibits highly selective and sensitive recognition toward Cu2+ in aqueous solution via a naked eye colour change from colourless to yellow and toward Al3+ via a significant fluorescent enhancement in ethanol over a wide range of tested metal ions. This represents the first reported Salicylaldehyde Schiff-based sensor capable of detecting both Cu2+ and Al3+ using two different modes. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis and Spectroscopic Characterization of Some Hydrazone and 2<i>H</i> -benzopyranone Derivatives as Antitumor Agents
  作者：Hana M. A. Abumelha

  DOI：10.1002/jhet.3211

  日期：2018.7

  starting materials. The structures of the synthesized new compounds were confirmed by IR, 1H, 13C‐NMR, MS, and elemental analysis. Some hydrazone derivatives and N‐substituted 2H‐benzopyranone‐3‐carboxamides were evaluated for their anticancer activity against HepG‐2 cell lines. Some of these compounds shared good cytotoxicity.

  一系列新腙，2- ħ -苯并吡喃酮-3-甲酰胺和2- ħ -苯并吡喃酮-3- carbonylthiosemicarbazide衍生物是从烷基7-羟基-2-合成ħ -苯并吡喃酮-3-羧酸乙酯（1A，b）和二溴衍生物（图6a，b）是关键的起始材料。合成的新化合物的结构通过IR，1 H，13 C-NMR，MS和元素分析确定。一些衍生物和N取代的2 H评估了苯并吡喃酮-3-羧酰胺类药物对HepG-2细胞系的抗癌活性。这些化合物中的一些具有良好的细胞毒性。