bis-(o-hydroxylnaphthaldehyde)4-aminophenylether | 7108-00-1

• 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: bis-(o-hydroxylnaphthaldehyde)4-aminophenylether
• 英文别名: 4,4’-bis(2-hydroxynaphthylmethylideneamino)diphenyl ether；1,1'-((1E,1'E)-((oxy-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))bis-(naphthalen-2-ol)；Bis-(4-<2-hydroxy-(1)naphthylmethenamino>-phenyl)-aether；4,4'-Bis-(2-hydroxy-1-naphthylmethylenamino)-diphenylether；1,1'-(4,4'-oxybis(4,1-phenylene)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)dinaphthalen-2-ol；2-HNA；1,1'-{Oxybis[(1,4-phenylene)iminomethyl]}-bis(2-naphthol)；1-[[4-[4-[(2-hydroxynaphthalen-1-yl)methylideneamino]phenoxy]phenyl]iminomethyl]naphthalen-2-ol
• CAS: 7108-00-1
• 化学式: C₃₄H₂₄N₂O₃
• 分子量: 508.576
• InChiKey: VDYXNGWHDBGZLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  39
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  bis-(o-hydroxylnaphthaldehyde)4-aminophenylether 、 巯基乙酸 以 苯 为溶剂， 以89%的产率得到3,3'-(oxybis(4,1-phenylene))bis(2-(2-hydroxynaphthalen-1-yl)thiazolidin-4-one)
  参考文献：
  名称：

  Rojin; Maher; Shireen, Indian Journal of Heterocyclic Chemistry, 2022, vol. 32, # 3, p. 357 - 362

  摘要：

  DOI：
• 作为产物：
  描述：

  4,4'-二氨基二苯醚 、 2-羟基-1-萘甲醛 以 甲醇 为溶剂， 反应 1.0h， 生成 bis-(o-hydroxylnaphthaldehyde)4-aminophenylether
  参考文献：
  名称：

  含双-O，N-二齿席夫碱配体的双核Pd（II）配合物：合成，表征，DFT研究和作为Suzuki-Miyaura偶联催化剂的应用

  摘要：

  摘要双核Schiff碱配体与[PdCl2（PPh3）2]和[Pd（OAc）2]的反应提供了[Pd2（L）2]和[Pd2Cl2]类型的双核钯（II）Schiff碱配合物新家族。 （PPh3）2（L）]。所有的钯配合物都是空气稳定的，并通过元素分析，FT-IR，UV-Vis和1H NMR光谱法充分表征。这些钯（II）席夫碱配合物表现出特征性的金属到配体的电荷转移（MLCT）跃迁。还进行了量子力学计算，以研究电子结构，分配振动光谱，并确定上述配合物的前沿分子轨道和吸收光谱的性质。

  DOI：

  10.1016/j.poly.2018.10.058

文献信息

• Phenolate based metallomacrocyclic xanthate complexes of Co^II/Cu^II and their exclusive deployment in [2 : 2] binuclear N,O-Schiff base macrocycle formation and in vitro anticancer studies
  作者：Vinay K. Singh、Rahul Kadu、Hetal Roy、Pallepogu Raghavaiah、Shaikh M. Mobin

  DOI：10.1039/c5dt03407h

  日期：——

  Crystallographic and in vitro anticancer studies of phenolate based Co^II/Cu^II xanthate metallomacrocycles and their N,O-Schiff base derivatives.

  基于酚酚基Co^II/Cu^II黄羧酸金属大环化合物的晶体学和体外抗癌研究以及它们的N,O-席夫碱衍生物。
• Binuclear half-sandwich ruthenium(II) Schiff base complexes: Synthesis, characterization, DFT study and catalytic activity for the reduction of nitroarenes
  作者：Raja Nandhini、Bellie Sundaram Krishnamoorthy、Galmari Venkatachalam

  DOI：10.1016/j.jorganchem.2019.120984

  日期：2019.12

  The binuclear ruthenium(II) p-cymene complexes containing Schiff base ligands of general composition [(Ru(p-cymene)Cl)2L1-6] (1-6) have been synthesized. The complexes were characterized by analytical and spectral (FT−IR, UV–Vis & 1H NMR) methods. The molecular structure of the representative complex [(Ru(p-cymene)Cl)2(L6)] (6) was determined by single-crystal X-ray diffraction and density functional

  合成了具有一般组成[（Ru（对-cymene）Cl）2 L 1-6 ]（1-6）的席夫碱配体的双核钌（II）对-cymene配合物。通过分析和光谱（FT-IR，UV-Vis和1 H NMR）方法对复合物进行了表征。通过单晶X射线衍射和密度泛函理论（DFT）计算来确定代表性络合物[（Ru（p- cymene）Cl）2（L 6）] （6）的分子结构。此外，这些半三明治钌络合物是在NaBH存在下将硝基芳烃温和氢化为芳族苯胺的活性催化剂在乙醇中加4。发现最有效的催化剂6与各种官能团的硝基芳烃相容。
• Spectroscopic Studies and Keto-Enol Tautomeric Effect of Newer Schiff Bases of ortho-Hydroxy-benzaldehyde/naphthaldehyde with 1,2-Phenylenediamine and 4-Aminophenyl Ether
  作者：Ambreen Shah、Asif A. Shah

  DOI：10.14233/ajchem.2013.13906

  日期：——

  Hydroxyl Schiff bases derived from 1,2-phenylenediamine and 4-aminophenyl ether with o-hydroxy benzaldehyde or o-hydroxyl naphthaldehyde were used to investigate enol-imine and keto-amine tautomeric analysis. UV-visible spectra of the compounds have been investigated tautomeric equilibrium (enol-imine O-H···N, keto- amine O···H-N forms) in different polar and non-polar solvents systems. From FTIR spectra of these model compounds, were possible to assign the IR absorption for the C=O and C=N groups in both keto-amine and enol imine forms, respectively. The keto-enol forms was observed in basic solution of polar and nonpolar solvents such as ethanol, chloroform, DMF, benzene, cyclohexane, n-hexane and in acidic solutions of CHCl3, benzene and n-hexane not in ethanol and DMF. FTIR results were showed that all Schiff bases studied, favoured the enol-imine form over the keto form in a weakly polar solvent.

  由1,2-苯二胺和4-氨基苯醚与邻羟基苯甲醛或邻羟基萘甲醛衍生的羟基希夫碱被用于研究烯醇-亚胺和酮-胺的互变异构体分析。化合物的紫外可见光谱已被用于调查不同极性和非极性溶剂体系中的互变平衡（烯醇-亚胺 O-H···N，酮-胺 O···H-N 形式）。通过这些模型化合物的傅里叶变换红外光谱（FTIR），可以分别分配C=O和C=N基团在酮-胺和烯醇-亚胺形式中的红外吸收。酮-烯醇形式在极性和非极性溶剂（如乙醇、氯仿、DMF、苯、环己烷、正己烷）碱性溶液中被观测到，而在氯仿、苯和正己烷的酸性溶液中则未在乙醇和DMF中观测到。FTIR结果表明，所有研究的希夫碱在弱极性溶剂中更倾向于烯醇-亚胺形式，而非酮形式。
• Synthesis of a Novel Fluorescent Schiff Base as a Possible Cu(II) Ion Selective Sensor
  作者：Mehmet Yıldırım、İsmet Kaya

  DOI：10.1007/s10895-010-0620-6

  日期：2010.5

  In this study a new fluorescent Schiff base; 1,1′-(4,4′-oxybis(4,1-phenylene)bis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)dinaphthalen-2-ol (2-HNA) was synthesized and characterized by FT-IR, UV-vis, and 1H and 13C-NMR techniques. Photoluminescent properties of 2-HNA were investigated in different solvents including methanol, THF, DMF, DMSO, acetone, acetonitrile, and dichloromethane. 2-HNA was found to have higher emission intensity and Stoke’s shift value (∆λST) in methanol solution. Relative emission intensity changes (I0−I/I0) of 2-HNA in methanol/water mixtures depending on different Cu+2 ion concentrations were determined and a linearized plot was obtained. Possible interference of some other transition metal ions was also determined. Sensitivity limit of the new sensor was found to be higher than 5 × 10−7 mol/L. 2-HNA has quite high selectivity against Cu+2 ion and, thus, can be used as a new fluorescence Cu+2 ion sensor in practice.

  本研究合成了一种新型荧光希夫碱：1,1′-(4,4′-氧双(4,1-亚苯基)双(偶氮-1-基-1-亚基))双(甲烷-1-基-1-亚基)二萘-2-醇（2-HNA），并利用傅立叶变换红外光谱、紫外可见光谱、1H 和 13C-NMR 技术对其进行了表征。研究了 2-HNA 在不同溶剂（包括甲醇、THF、DMF、DMSO、丙酮、乙腈和二氯甲烷）中的光致发光特性。发现 2-HNA 在甲醇溶液中具有更高的发射强度和斯托克偏移值（∆λST）。根据不同的 Cu+2 离子浓度，测定了 2-HNA 在甲醇/水混合物中的相对发射强度变化（I0-I/I0），并得到了线性化曲线图。此外，还测定了其他一些过渡金属离子可能造成的干扰。新传感器的灵敏度极限高于 5 × 10-7 mol/L。2-HNA 对 Cu+2 离子具有相当高的选择性，因此可作为一种新型荧光 Cu+2 离子传感器用于实际应用。