4-hydroxysalicylaldehyde N-benzoylhydrazone | 71040-04-5

• 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: 4-hydroxysalicylaldehyde N-benzoylhydrazone
• 英文别名: N'-(2,4-dihydroxybenzylidene)benzohydrazide；N-[(2,4-dihydroxyphenyl)methylideneamino]benzamide
• CAS: 71040-04-5
• 化学式: C₁₄H₁₂N₂O₃
• mdl: MFCD00033258
• 分子量: 256.261
• InChiKey: CCCOIIPPDUTXBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 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：
  81.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-hydroxysalicylaldehyde N-benzoylhydrazone 在 lead(IV) tetraacetate 作用下， 以 四氢呋喃 为溶剂， 以3%的产率得到2-苯甲酰基-4-羟基苯甲醛
  参考文献：
  名称：

  多功能和区域特异性合成功能化的1,3-二芳基异苯并呋喃。

  摘要：

  已经开发了方便，通用和区域特异性的官能化的1，3-二芳基异苯并呋喃合成。它涉及芳基镁试剂的化学选择性加成至邻-芳酰基苯甲醛的醛官能团，其本身可通过水杨醛的N-芳酰基hydr的四乙酸铅氧化而容易地获得。因此已将各种官能团，包括硝基，碘或酯官能团，以完全的区域专一性定位在1，3-二苯基异苯并呋喃骨架上。

  DOI：

  10.1021/ol801550a
• 作为产物：
  描述：

  苯甲酸乙酯 在 hydrazine hydrate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 4-hydroxysalicylaldehyde N-benzoylhydrazone
  参考文献：
  名称：

  取代的水杨醛，酰肼和磺酰肼的合成及抗真菌活性

  摘要：

  通过将相应的羧酸转化成由Amberlyst-15催化的甲酯，然后与一水合肼反应，开发出了用于制备酰肼和酰肼的有效合成方法。磺酰肼由相应的磺酰氯和肼一水合物制备。使用梯度浓缩方法将这两组化合物与取代的水杨醛缩合，生成大量的,、酰肼和磺酰肼类似物库。制备的类似物的抗真菌活性表明，水杨醛hydr和酰肼是有效的真菌生长抑制剂，几乎没有哺乳动物细胞毒性，这使这些类似物成为未来治疗发展的新靶标。

  DOI：

  10.1016/j.bmc.2014.07.022

文献信息

• Mixed polymeric micelles as a multifunctional visual thermosensor for the rapid analysis of mixed metal ions with Al³⁺ and Fe³⁺
  作者：Juan Han、Yunfeng Cai、Yun Wang、Xiaohui Dai、Lei Wang、Chunmei Li、Baodong An、Liang Ni

  DOI：10.1039/c8nj01917g

  日期：——

  The detection limits using 0.05 g L−1 mixed micelles for the analysis of Al3+ and Fe3+ ions decreased from ∼5.95 to ∼4.02 nM, and ∼30.30 nM to ∼23.84 nM, respectively, upon changing the temperature from 25 °C to 40 °C. Furthermore, the mixed micelles in combination with Principal Component Analysis (PCA) and linear regression analysis to establish prediction models were used to achieve the successful

  一种新的类型的响应混合双亲水性嵌段共聚物（DHBC）的多官能的基于视觉感温（与聚的混合共聚物（环氧乙烷） - b -聚（Ñ -isopropylacrylAMide-共-2,4-甲基苯甲醛肟），（PEG - b -P（NIPAM-共-BDMa））和聚（环氧乙烷） - b -聚（ñ -isopropylacrylAMide-共-RhodAMine 6G甲基丙烯酸）（PEG- b -P（NIPAM-共-Rh6GEMa））） ，用于检测Al 3+和Fe 3+是基于可逆加成-断裂链转移（RAFT）聚合设计和合成的。对传感过程的研究表明，该多功能视觉热传感器对Al 3+和Fe 3+离子具有比许多与环境有关的离子优良的选择性，并且具有纳摩尔级检测极限的高灵敏度。此外，多功能视觉热传感器可在温度升高时以（P（NIPAM- co -BDMa）/ P（NIPAM- co -Rh6GEMa））嵌段为核心，而溶
• A salicylaldehyde benzoyl hydrazone based near-infrared probe for copper(<scp>ii</scp>) and its bioimaging applications
  作者：Jie Zhao、Yue-yuan Wang、Wen-ling Chen、Guang-shu Hao、Jian-ping Sun、Qing-fang Shi、Fang Tian、Run-tian Ma

  DOI：10.1039/d1ra08616b

  日期：——

  clinical copper-related disease diagnosis. In this work, a near infrared (NIR) fluorescent probe, CySBH, with a salicylaldehyde benzoyl hydrazone group as a selective and sensitive receptor for Cu2+ was designed and synthesized. The specific coordination of the salicylaldehyde benzoyl hydrazone group in CySBH with Cu2+ can induce a distinct quench of the fluorescence intensity, allowing for real-time tracking

  开发高灵敏度和选择性检测生命系统中Cu 2+的方法对于临床铜相关疾病的诊断具有重要意义。在这项工作中，设计并合成了一种近红外（NIR）荧光探针CySBH，它具有水杨醛苯甲酰腙基团作为Cu 2+的选择性和敏感受体。CySBH中的水杨醛苯甲酰腙基团与Cu 2+的特异性配位可以引起荧光强度的明显猝灭，从而实现对Cu 2+的实时跟踪。我们已经证明 CySBH 可以快速识别 Cu 2+具有良好的选择性和高灵敏度。此外，在低细胞毒性的基础上，该探针用于通过荧光成像对两个细胞系中的Cu 2+进行可视化。此外，由于其近红外发射特性，CySBH 还可用于体内监测 Cu 2+ 。 这些总体结果表明，近红外荧光探针 CySBH 为生命系统中 Cu 2+的选择性和灵敏监测提供了一种新方法。
• A simple turn-on fluorescent chemosensor based on Schiff base-terminated water-soluble polymer for selective detection of Al3+ in 100% aqueous solution
  作者：Liping Bai、Farong Tao、Leixuan Li、Aixia Deng、Chunna Yan、Guang Li、Liping Wang

  DOI：10.1016/j.saa.2019.02.062

  日期：2019.5

  A simple water-soluble polymer PEGBHB based on polyethylene glycol bearing a Schiff base derivative moiety was successfully designed and synthesized. PEGBHB showed high selectivity and sensitivity towards Al3+ as a turn-on fluorescent chemosensor without influence by other competitive metal ions in 100% aqueous solution. The detection limit of PEGBHB for Al3+ was found to be 9.67 × 10−9 M. A 1:1 stoichiometry

  成功设计并合成了一种基于带有席夫碱衍生物部分的聚乙二醇的简单水溶性聚合物PEGBHB。PEGBHB作为开启型荧光化学传感器，对Al 3+具有很高的选择性和灵敏度，而不受100％水溶液中其他竞争性金属离子的影响。PEGBHB为Al的检测限3+被发现是9.67×10 -9  M. A 1：PEGBHB和Al之间1个化学计量3+已按工作作图分析证实。PEGBHB可以在4至10的宽pH范围内检测到Al 3+。通过向EDGBHB-Al 3+溶液中添加EDTA，化学传感器是可逆的。复杂的。在将Al 3+和EDTA交替添加到化学传感器中时，借助OFF-ON-OFF信号构建了INHIBIT分子逻辑门。此外，使用PEGBHB方便地制作了试纸，以方便，直观地检测实际的Al 3+。
• Metal ions-triggered photo-induced fluorescence change in rhodamine B-based photo-responsive complexes
  作者：Yuanyuan Li、Zining Feng、Yajing Li、Wenhui Jin、Qiuchen Peng、Panke Zhang、Juan He、Kai Li

  DOI：10.1016/j.saa.2020.118069

  日期：2020.4

  Photo-responsive materials with tunable properties by multiple stimuli have been widely used as molecular machines, molecular logic gates, optical data storages, etc. In this work, we report a rhodamine B-based photoresponsive system, whose properties could be facilely modulated by metal ions (Zn(II). Ni(II) and Hg(II)). These metal ions endow the complexes (L-Zn, L-Ni and L-Hg) with similar photochromic property but distinctly different photo-induced fluorescence change. Upon UV light irradiation, the spirolactam ring in rhodamine B moiety turned from a close form to an open form, along with enlarged conjugated structure with intense absorbance. Interestingly, fluorescence "turn off", "no change" and "turn on" responses were induced by Zn(II), Ni(II) and Hg(II) respectively upon UV light irradiation. Taking advantage of the prominently different characteristics caused by metal ions, different logic gates were designed by simply varying the inputs of metal ions and UV light. This work provided a new strategy for developing multifunctional photo-responsive materials, which were further beneficial for constructing photo-controlled logic gates with tunable performance. (C) 2020 Elsevier B.V. All rights reserved.
• Structural investigations of aroylhydrazones derived from nicotinic acid hydrazide in solid state and in solution
  作者：Nives Galić、Ivan Brođanac、Darko Kontrec、Snežana Miljanić

  DOI：10.1016/j.saa.2013.01.028

  日期：2013.4

  Structural forms of aroylhydrazones derived from nicotinic acid hydrazide have been studied in the solid state by FT-IR spectroscopy and in solution by NMR, UV-Vis and ATR spectroscopy. The studied compounds were N'-benzylidene-3-pyridinecarbohydrazide (I), N'-(2,4-dihydroxyphenylmethylidene)-3-pyridine-carbohydrazide (2), N'-(5-chloro-2-hydroxyphenylmethylidene)-3-pyridinecarbohydrazide (3), and N'-(3,5-dichloro-2-hydroxymethoxyphenylmethylidene)-3-pyridinecarbohydrazide (4). The compound 1 adopted the most stable ketoamine form (form I,-CO-NH-N=C-) in the solid state as well as in various organic solvents. In mixtures of organic solvents with water the UV-Vis and ATR spectra implied intermolecular hydrogen bonding of 1 with water molecules. The presence of both tautomeric forms land II (form II, -COH=N-N=C-) was proposed for the solid substance and highly concentrated solutions of 2, whereas form I was detected as the predominant one in diluted solutions. For compounds 3 and 4a coexistence of forms land III (form III,-CO-NH-NH-C=C-CO-) was noticed in the solid state and in polar protic organic solvents. The conversion to form III was induced by increasing the water content in the solvent mixtures. This process was the most pronounced for compound 4. When exposed to daylight, an appearance of a new band was observed during time in the UV-Vis spectrum of 4 in organic solvent/water 1/1 mixtures, which implied that tautomeric interconversion was most likely followed by E/Z isomerisation. (C) 2013 Elsevier B.V. All rights reserved.