5-[(E)-2-(2-methoxyphenyl)-1-diazenyl]-2-hydroxybenzoic acid | 948898-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 5-[(E)-2-(2-methoxyphenyl)-1-diazenyl]-2-hydroxybenzoic acid
• CAS: 948898-76-8
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: QNNHJQIDIIIMHV-FOCLMDBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  91.48
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-(2-methoxyphenyl)-1-diazenyl]-2-hydroxybenzoic acid 、 氧化二辛基锡 以 甲苯 为溶剂， 以50%的产率得到([(n)Oct2Sn(5-[(E)-2-(2-methoxyphenyl)-1-diazenyl]-2-hydroxybenzoate)]2O)2
  参考文献：
  名称：

  Di-n-octyltin(IV) complexes with 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acid: Syntheses and assessment of solid state structures by 119Sn Mössbauer and X-ray diffraction and further insight into the solution structures using electrospray ionization MS, 119Sn NMR and variable temperature NMR spectroscopy

  摘要：

  Reactions of 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acids (LHH', where the aryl group is an R-substituted phenyl ring such that for L'HH':X = H; (LHH)-H-2':X=2'-OCH3; (LHH)-H-3':X = 3'-CH3; (LHH)-H-4':X = 4'-CH3; (LHH)-H-5':X = 4'-Cl) with (n)Oct(2)SnO in 2:1 and 1:1 molar ratios have been investigated. Two types of complexes, (n)Oct(2)Sn(LH)(2) and {[(n)Oct(2)Sn(LH)(2)O}(2), were isolated and they have been characterized by H-1, C-13, Sn-119 NMR, ESI-MS, IR and Sn-119m Mossbauer spectroscopic techniques in combination with elemental analyses. The crystal structures of nOct(2)Sn((LH)-H-1)(2) (1), {[(n)Oct(2)Sn((LH)-H-1)](2)O}(2) (3) and {[(n)Oct(2)Sn((LH)-H-3)(2)O}(2) (4) were determined. The mononuclear complex 1 was found to adopt a skew-trapezoidal bipyramidal arrangement around the tin atom while 3 and 4 are centrosymmetric tetranuclear bis(dicarboxylatotetrabutyldistannoxane) complexes containing a planar Sn4O2 core in which two mu(3)-Oxo O-atoms connect an Sn2O2 ring to two exocyclic Sn-atoms. The solution structures were confirmed by 119Sn NMR spectroscopy by observing one tin resonance in compound 1 and two tin resonances in {[(n)Oct(2)Sn((LH)-H-5)(2)O}(2) (5). {[(n)Oct(2)Sn((LH)-H-2)](2)O}(2) (3) and {[(n)Oct(2)Sn((LH)-H-3)](2)O}(2) (4) undergo very complex exchange processes in deuteriochloroform solution, which has been confirmed by variable temperature H-1 NMR spectroscopy. The cleavage of the most labile bond in the molecule was studied by ESI mass spectrometry. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.04.044
• 作为产物：
  描述：

  邻甲氧基苯胺 、 水杨酸 以31.5%的产率得到5-[(E)-2-(2-methoxyphenyl)-1-diazenyl]-2-hydroxybenzoic acid
  参考文献：
  名称：

  Di-n-octyltin(IV) complexes with 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acid: Syntheses and assessment of solid state structures by 119Sn Mössbauer and X-ray diffraction and further insight into the solution structures using electrospray ionization MS, 119Sn NMR and variable temperature NMR spectroscopy

  摘要：

  Reactions of 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acids (LHH', where the aryl group is an R-substituted phenyl ring such that for L'HH':X = H; (LHH)-H-2':X=2'-OCH3; (LHH)-H-3':X = 3'-CH3; (LHH)-H-4':X = 4'-CH3; (LHH)-H-5':X = 4'-Cl) with (n)Oct(2)SnO in 2:1 and 1:1 molar ratios have been investigated. Two types of complexes, (n)Oct(2)Sn(LH)(2) and {[(n)Oct(2)Sn(LH)(2)O}(2), were isolated and they have been characterized by H-1, C-13, Sn-119 NMR, ESI-MS, IR and Sn-119m Mossbauer spectroscopic techniques in combination with elemental analyses. The crystal structures of nOct(2)Sn((LH)-H-1)(2) (1), {[(n)Oct(2)Sn((LH)-H-1)](2)O}(2) (3) and {[(n)Oct(2)Sn((LH)-H-3)(2)O}(2) (4) were determined. The mononuclear complex 1 was found to adopt a skew-trapezoidal bipyramidal arrangement around the tin atom while 3 and 4 are centrosymmetric tetranuclear bis(dicarboxylatotetrabutyldistannoxane) complexes containing a planar Sn4O2 core in which two mu(3)-Oxo O-atoms connect an Sn2O2 ring to two exocyclic Sn-atoms. The solution structures were confirmed by 119Sn NMR spectroscopy by observing one tin resonance in compound 1 and two tin resonances in {[(n)Oct(2)Sn((LH)-H-5)(2)O}(2) (5). {[(n)Oct(2)Sn((LH)-H-2)](2)O}(2) (3) and {[(n)Oct(2)Sn((LH)-H-3)](2)O}(2) (4) undergo very complex exchange processes in deuteriochloroform solution, which has been confirmed by variable temperature H-1 NMR spectroscopy. The cleavage of the most labile bond in the molecule was studied by ESI mass spectrometry. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2007.04.044