2-oxo-1,2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone | 880052-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone
• 英文别名: 2-oxo-1, 2-dihydroquinoline-3-carbaldehyde benzhydrazide；2-oxo-quinoline-3-carbaldehyde-benzoyl hydrazone；N-[(2-oxo-1H-quinolin-3-yl)methylideneamino]benzamide
• CAS: 880052-47-1
• 化学式: C₁₇H₁₃N₃O₂
• 分子量: 291.309
• InChiKey: HWNDQTGOBAGQOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  aluminium trinitrate 、 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone 以 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  A simple quinoline derivative as fluorescent probe with high sensitivity and selectivity for Al3+ in aqueous solution

  摘要：

  A simple Al3+ receptor, 2-hydroxyquinoline-3-aldehyde-(benzoyl)hydrazone (L), has been synthesized by condensing 2-hydroxyquinoline-3-aldehyde with benzoic hydrazide. L displayed a high selectivity and pronounced fluorescence enhancement for Al3+ over other common cations in water. Moreover, based on the Job's plot, ESI-MS spectrometry, it could be considered that L and Al3+ were coordinated with a 1:1 ratio. In addition, the detection limit of L for sensing Al3+ was calculated to be 7.21 x 10(-8) M, which was lower than the acceptable limit of Al3+ level in drinking water defined by World Health Organization (WHO) (1.85 x 10(-6) M). These results indicated that this chemical sensor L could be used as a serviceable molecular probe for practical applications. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.10.011
• 作为产物：
  描述：

  N-乙酰苯胺 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone
  参考文献：
  名称：

  具有异常电子结构和单离子磁体特征 的混合价金属化合物[Co III 2 Co II 2 ] †

  摘要：

  在没有任何碱的情况下，多位配位配体（H 2 L）与Co（Ac）2 ·4H 2 O的反应提供了均金属的四核混合价配合物[Co 4（L）4（CH 3 CO 2）2（CH 3 OH）2 ]·Et 2 O（1）。该混合价金属螯合物[Co 4（L）4（CH 3 CO 2）2（CH 3 OH）2 ]·Et 2 O（1）已进行了理论和实验分析，以反式-[Co III ls –Co II hs –Co III ls –Co II hs ]的形式指定化合价和自旋态。HF-EPR揭示了在局部高自旋钴中心存在明显的横向分量（E = 9.5 cm -1）的轴向各向异性（D = -34.4 cm -1）。在直流场的存在下观察到慢的磁弛豫效应，表明场感应的单离子磁行为，这与金属对化物内Co（II）的异常电子结构有关。

  DOI：

  10.1039/c7dt00564d

文献信息

• Ruthenium(II) carbonyl complexes containing bidentate 2-oxo-1,2-dihydroquinoline-3-carbaldehyde hydrazone ligands as efficient catalysts for catalytic amidation reaction
  作者：Sellappan Selvamurugan、Rangasamy Ramachandran、Govindan Prakash、Periasamy Viswanathamurthi、Jan Grzegorz Malecki、Akira Endo

  DOI：10.1016/j.jorganchem.2015.11.017

  日期：2016.2

  2-dihydroquinoline-3-carbaldehyde hydrazone ligands in ruthenium(II) and the catalytic activity of newly synthesized complexes have been studied. The complexes [RuCl(CO)(PPh3)2(L1)] (1), [RuCl(CO)(AsPh3)2(L1)] (2), [RuCl(CO)(PPh3)2(L2)] (3) and [RuCl(CO)(AsPh3)2(L2)] (4) were synthesized by reactions of [RuHCl(CO)(EPh3)3] (E = P or As) precursors with hydrazone ligands and characterized by analytical and spectroscopic

  研究了钌（II）中2-氧-1,2-二氢喹啉-3-咔醛coordination配体的配位行为和新合成配合物的催化活性。络合物[RuCl（CO）（PPh 3）2（L 1）]（1），[RuCl（CO）（AsPh 3）2（L 1）]（2），[RuCl（CO）（PPh 3）2通过[RuHCl（CO）（EPh 3）3反应，合成了（L 2）]（3）和[RuCl（CO）（AsPh 3）2（L 2）]（4）。]（E = P或As）的前体，具有by配体，并通过分析和光谱学方法进行了表征。配合物2的分子结构通过单晶X射线衍射分析鉴定。结构分析表明，所有配合物均具有扭曲的八面体几何形状，配体以单负双齿NO方式配位。此外，在醇与胺直接酰胺化的情况下，已经研究了配合物的催化效率。还评估了碱，反应温度和催化剂用量在酰胺化反应中的影响。值得注意的是，复杂3据发现，它是将醇与胺酰胺化的非常有效的催化剂。具有各种官能团的多种芳族（杂）胺和醇也已成功地用于酰胺化。
• Crystal structures, DNA-binding and cytotoxic activities studies of Cu(II) complexes with 2-oxo-quinoline-3-carbaldehyde Schiff-bases
  作者：Zeng-Chen Liu、Bao-Dui Wang、Bo Li、Qin Wang、Zheng-Yin Yang、Tian-Rong Li、Yong Li

  DOI：10.1016/j.ejmech.2010.08.060

  日期：2010.11

  Three novel 2-oxo-quinoline-3-carbaldehyde Schiff-bases and their Cu(II) complexes were synthesized. The molecular structures of Cu(II) complexes were determined by X-ray crystal diffraction. The DNA-binding modes of the complexes were also investigated by UV vis absorption spectrum, fluorescence spectrum, viscosity measurement and EB-DNA displacement experiment. The experimental evidences indicated that the ligands and Cu(II) complexes could interact with CT-DNA (calf-thymus DNA) through intercalation, respectively. Comparative cytotoxic activities of ligands and Cu(II) complexes were also determined by MTT [3-(4,5-dimethyl-2-thiazoyl)-2,5-diphenyl-2H-tetrazolium bromide] and SRB (sulforhodamine B) methods. The results showed that the three Cu(II) complexes exhibited more effective cytotoxic activity against HL60 cells and HeLa cells than corresponding ligands. Also, CuL3 showed higher cytotoxic activity than CuL1 and CuL2 (C) 2010 Elsevier Masson SAS. All rights reserved.
• Synthesis, crystal structure and pharmacological evaluation of two new Cu(II) complexes of 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone: A comparative investigation
  作者：Duraisamy Senthil Raja、Nattamai S.P. Bhuvanesh、Karuppannan Natarajan

  DOI：10.1016/j.ejmech.2011.10.024

  日期：2012.1

  Two new copper(II) complexes have been synthesized by reacting 2-oxo-1,2-dihydroquinoline-3-carbaldehyde (benzoyl) hydrazone (H2L) with CuCl2 center dot 2H(2)O or Cu(NO3)(2)center dot 3H(2)O. The structures of the complexes have been determined by single crystal X-ray diffraction studies. Results obtained using spectroscopic methods strongly suggested that the ligand and its Cu(II) complexes could interact with calf thymus DNA through intercalation. In the case of protein binding, the obtained results indicated that all the three compounds could quench the intrinsic fluorescence of bovine serum albumin through static quenching process. In addition, antioxidant activity tests showed that H2L and its copper(II) complexes possess significant scavenging effect against free radicals. Further, the two copper(II) complexes exhibited effective cytotoxic activity against a panel of human cancer cell lines. (C) 2011 Elsevier Masson SAS. All rights reserved.