N-(2-hydroxy-1-naphthylidene)aminopyrimidine | 148642-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(2-hydroxy-1-naphthylidene)aminopyrimidine
• 英文别名: 1-((pyrimidin-2-ylimino)methyl)naphthalen-2-ol；1-((pyrimidine-2-ylimino)methyl)naphthalene-2-ol；1-((pyrimidin-2-ylimino)methyl)naphthalene-2-ol；1-(Pyrimidin-2-yliminomethyl)-naphthalen-2-ol；1-(pyrimidin-2-yliminomethyl)naphthalen-2-ol
• CAS: 148642-24-4
• 化学式: C₁₅H₁₁N₃O
• 分子量: 249.272
• InChiKey: QPIQQOASISHHEZ-UHFFFAOYSA-N

物化性质

• 沸点：
  501.9±52.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-hydroxy-1-naphthylidene)aminopyrimidine 、 2-氨基苯酚 在 甲酸 作用下， 以 水 为溶剂， 反应 0.42h， 以88%的产率得到1-[[(2-羟基苯基)亚胺]甲基]-2-萘酚
  参考文献：
  名称：

  A novel approach toward the synthesis of some new tridentate Schiff bases from anil-like compounds

  摘要：

  从羟基萘嘧啶胺开始，开发了一种合成一系列新的三齿 希夫碱配体的新方法。 与邻苯二胺、邻氨基苯酚或 2-氨基-3-羟基吡啶在无溶剂条件下催化合成了一系列新的三齿状希夫碱配体。 在无溶剂条件下，在甲酸催化剂的存在下进行。在这些反应中 在这些反应中，得到了作为半单位配体的 [1+1] 缩合产物。 此外，羟基萘嘧啶胺与 3,4-二氨基吡啶和 1,8-萘二胺反应，生成了 分别生成 C2-萘基咪唑吡啶和二氢嘧啶。该 该方案的诱人之处在于：使用廉价催化剂、 操作简单、反应时间短、易于处理和收率高。

  DOI：

  10.2298/jsc151202064b
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 3.0h， 生成 N-(2-hydroxy-1-naphthylidene)aminopyrimidine
  参考文献：
  名称：

  Synthesis, Characterization, DNA Cleavage, and Antimicrobial Studies of Some Transition Metal Complexes With a Novel Schiff Base Derived From 2-Aminopyrimidine

  摘要：

  Complexes of manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) with a Schiff base formed by the condensation of 2-aminopyrimidine with 2-hydroxy-1-naphthaldehyde were synthesized and characterized on the basis of elemental analysis, molar conductance, magnetic susceptibility data, UV-vis, IR, FAB mass, and 1H and 13C NMR spectral studies. The Schiff base can exhibit enolimine-quinoneamine tautomerism. In the solid state the ligand existed in the enolimine form. However, in solution it existed in the quinoneamine tautomeric form. But on complexation with the metal ions, the ligand existed in the imine form. The spectral data revealed that the ligand acted as monobasic bidentate coordinating to the metal ions through azomethine nitrogen and deprotonated naphtholate oxygen. Molar conductance values adequately supported the nonelectrolytic nature of the complexes. All the complexes exhibited 1:2 metal-ligand stochiometry. Based on electronic spectral data and magnetic moment values, suitable geometry has been proposed for each complex. The copper(II) complex has been subjected to thermal decomposition studies. The XRD pattern of the copper(II) complex indicated an orthorhombic crystal lattice. The ligand and the metal complexes were screened for their antibacterial and antifungal activities by disc diffusion method. DNA cleavage efficiency of the ligand and the complexes were monitored by gel electrophoresis method.

  DOI：

  10.1080/15533174.2012.740711

文献信息

• Novel Synthetic Approach for the Access of Functionalised 4H-Chromenes
  作者：Mahdieh Sadeghpour、Fatemeh Bagheri

  DOI：10.3184/174751916x14792153319761

  日期：2016.12

  A simple, efficient and high-yielding one-pot protocol for the synthesis of novel functionalised 4H-chromenes and chromene carboxylic acids has been developed using multi-component domino coupling reactions of anil-like compounds with 1,3-diketones and indole in the presence of formic acid catalyst under solvent-free conditions. The protocol avoids the use of expensive catalysts, toxic solvents and

  使用类苯胺化合物与 1,3-二酮和吲哚的多组分多米诺偶联反应，开发了一种简单、高效和高产的单锅法，用于合成新型官能化 4H-色烯和色烯羧酸。在无溶剂条件下存在甲酸催化剂。该协议避免使用昂贵的催化剂、有毒溶剂和色谱分离。
• Antimicrobial, antioxidant, and in silco studies of divalent metal complexes of novel aminopyrimidine Schiff base chelators
  作者：Festus Chioma、Obinna Okpareke、Sunday N. Okafor、Chizoba I. Ezugwu

  DOI：10.1016/j.molstruc.2023.136070

  日期：2023.11
• A novel approach toward the synthesis of some new tridentate Schiff bases from anil-like compounds
  作者：Fatemeh Bagheri、Abolfazl Olyaei

  DOI：10.2298/jsc151202064b

  日期：——

  A novel method was developed for synthesizing a series of new three dentate Schiff base ligands starting from hydroxynaphthalidene pyrimidinyl amines with o-phenylenediamines or o-aminophenol or 2-amino-3-hydroxy-pyri-dine in the presence of formic acid catalyst under solvent-free conditions. In these reactions [1+1] condensation product as half-unit ligand was obtained. Moreover, the reaction of hydroxynaphthalidene pyrimidinyl amines with 3,4-diamino-pyridine and 1,8-naphthalenediamine lead to the formation of C2-naphthylated imidazopyridine and dihydropyrimidine, respectively. The attractive features of this protocol are: use of inexpensive catalyst, operationally simple, short reaction times, easy handling, and good yields.

  从羟基萘嘧啶胺开始，开发了一种合成一系列新的三齿 希夫碱配体的新方法。 与邻苯二胺、邻氨基苯酚或 2-氨基-3-羟基吡啶在无溶剂条件下催化合成了一系列新的三齿状希夫碱配体。 在无溶剂条件下，在甲酸催化剂的存在下进行。在这些反应中 在这些反应中，得到了作为半单位配体的 [1+1] 缩合产物。 此外，羟基萘嘧啶胺与 3,4-二氨基吡啶和 1,8-萘二胺反应，生成了 分别生成 C2-萘基咪唑吡啶和二氢嘧啶。该 该方案的诱人之处在于：使用廉价催化剂、 操作简单、反应时间短、易于处理和收率高。
• Synthesis, Characterization, DNA Cleavage, and Antimicrobial Studies of Some Transition Metal Complexes With a Novel Schiff Base Derived From 2-Aminopyrimidine
  作者：Y. Sindhu、C. J. Athira、M. S. Sujamol、R. Selwin Joseyphus、K. Mohanan

  DOI：10.1080/15533174.2012.740711

  日期：2013.3.1

  Complexes of manganese(II), cobalt(II), nickel(II), copper(II), and zinc(II) with a Schiff base formed by the condensation of 2-aminopyrimidine with 2-hydroxy-1-naphthaldehyde were synthesized and characterized on the basis of elemental analysis, molar conductance, magnetic susceptibility data, UV-vis, IR, FAB mass, and 1H and 13C NMR spectral studies. The Schiff base can exhibit enolimine-quinoneamine tautomerism. In the solid state the ligand existed in the enolimine form. However, in solution it existed in the quinoneamine tautomeric form. But on complexation with the metal ions, the ligand existed in the imine form. The spectral data revealed that the ligand acted as monobasic bidentate coordinating to the metal ions through azomethine nitrogen and deprotonated naphtholate oxygen. Molar conductance values adequately supported the nonelectrolytic nature of the complexes. All the complexes exhibited 1:2 metal-ligand stochiometry. Based on electronic spectral data and magnetic moment values, suitable geometry has been proposed for each complex. The copper(II) complex has been subjected to thermal decomposition studies. The XRD pattern of the copper(II) complex indicated an orthorhombic crystal lattice. The ligand and the metal complexes were screened for their antibacterial and antifungal activities by disc diffusion method. DNA cleavage efficiency of the ligand and the complexes were monitored by gel electrophoresis method.