5-[(E)-2-(3'-methylphenyl)-1-diazenyl]-2-hydroxybenzoic acid | 380360-47-4

• 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-(3'-methylphenyl)-1-diazenyl]-2-hydroxybenzoic acid
• 英文别名: 5-[(E)-2-(3-methylphenyl)-1-diazenyl]-2-hydroxybenzoic acid；(E)-2-hydroxy-5-[(3-methylphenyl)diazenyl]benzoic acid
• CAS: 380360-47-4
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: MEXNGKZQTAGDCC-FOCLMDBBSA-N

物化性质

• 沸点：
  495.7±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82.25
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  二正丁基氧化锡 、 5-[(E)-2-(3'-methylphenyl)-1-diazenyl]-2-hydroxybenzoic acid 以 甲苯 为溶剂， 以35.4%的产率得到([(n-butyl)2Sn(5-[(E)-2-(3'-methylphenyl)-1-diazenyl]-2-hydroxybenzoato)]2O)2
  参考文献：
  名称：

  Synthesis and characterization of bis[dicarboxylatotetraorganodistannoxane] units involving 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoic acids: An investigation of structures by X-ray diffraction, NMR, electrospray ionisation MS and assessment of in vitro cytotoxicity

  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 (LHH)-H-1': R = H; (LHH)-H-2': R = 2'-CH3; (LHH)-H-3': R = 3'-CH3; (LHH)-H-4': R = 4'-CH3; (LHH)-H-5': R = 4'-Cl; (LHH)-H-6': R = 4'-Br) with (Bu2SnO)-Bu-n in a 1:1 molar ratio yielded complexes of composition {[(Bu2Sn)-Bu-n(LH)](2)O}(2). The complexes 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 {[(Bu2Sn)-Bu-n((LH)-H-1)](2)O}(2) (1), {[(Bu2Sn)-Bu-n((LH)-H-4)](2)O}(2) (4), {[(Bu2Sn)-Bu-n((LH)-H-5)](2)O}(2) (5) and {[(Bu2Sn)-Bu-n((LH)-H-6)](2)O}(2) (6) were determined. The compounds 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 four carboxylate ligands display two different modes of coordination. where both modes involve bridging of two structurally distinct Sn-atoms. The solution structures were confirmed by Sn-119 NMR spectroscopy by observing two tin resonances in compounds 1, and 4-6. The observed difference between the two tin resonances was about 3 ppm while the differences in C-13 resonances were even smaller. Compounds {[(Bu2Sn)-Bu-n((LH)-H-2)](2)O}(2) (2) and {[(Bu2Sn)-Bu-n((LH)-H-3)](2)O}(2) (3) undergo a very complex exchange processes in deuteriochloroform solution. The in vitro cytotoxic activity of compounds 1 and 4 against WIDR, M19 MEL, A498, IGROV, H226, MCF7 and EVSA-T human tumour cell lines is reported. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.08.005
• 作为产物：
  描述：

  间甲苯胺盐酸盐 、 水杨酸 在 盐酸 、 sodium nitrite 、 sodium hydroxide 作用下， 以 水 为溶剂， 以50%的产率得到5-[(E)-2-(3'-methylphenyl)-1-diazenyl]-2-hydroxybenzoic acid
  参考文献：
  名称：

  5-[（E）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸的三有机锡（IV）配合物的合成与表征.. ：三苯基锡5-[（E）- 2-（芳基）-1-二氮烯基] -2-羟基苯甲酸酯（芳基=苯基，2-甲基苯基，3-甲基苯基和4-甲氧基苯基）

  摘要：

  的三苯基锡和三Ñ一些5 -butyltin络合物- [（ë）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸已经合成和表征通过1 H-，13 C-，119 Sn的NMR，IR和119m SnMössbauer光谱技术与元素分析相结合。报道了三苯基锡5-[（E）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸酯的晶体结构（芳基=苯基，2-甲基苯基，3-甲基苯基和4-甲氧基苯基）。X射线和119 SnMössbauer数据均表明三苯锡配合物采用单体扭曲的四面体构型，且羧酸盐配体以单齿模式配位。相比之下，119 SnMössbauer光谱表明，每个三丁基锡配合物都是聚合的，具有跨三角形的双锥体几何结构，具有平面的SnBu 3单元和两个双齿形的羧酸根配位体衍生而来的顶端的羧基氧原子。这是一种固态的效果，既是119 Sn-NMR的和1 Ĵ（13 C- 117分之119 Sn）的耦合常数的数据表明在溶液中四面体几何形状的三苯基-和三-

  DOI：

  10.1016/s0022-328x(01)01024-5

文献信息

• Structural diversity among some dialkyltin(IV) benzoate and related derivatives
  作者：Anthony Linden、Tushar S. Basu Baul

  DOI：10.1107/s2053229621003545

  日期：2021.5.1

  four bridging carboxylate ligands, plus two alkyl ligands at each SnIV centre. The complexes octabutyltetrakisμ‐(E)‐4‐[(4‐hydroxy‐3,5‐dimethylphenyl)diazenyl]benzoato}di‐μ3‐oxido‐tetratin(IV) ethanol disolvate, [Sn4(C4H9)8(C15H13N2O3)4O2]·2C2H6O, (IV), and octabutyltetrakis(E)‐3‐[(2‐hydroxybenzylidene)amino]propanoato}di‐μ3‐oxido‐tetratin(IV), [Sn4(C4H9)8(C10H10NO3)4O2], (V), display this motif. The

  五个二有机锡（IV）羧酸盐（I）-（V）的分子结构可归为此类锡配合物的两种主要的众所周知的结构类型。一种是具有[R 2 Sn（L H）2 ]型偏斜梯形双金字塔的单核二联激酶（IV）羧酸盐，其中烷基配体位于假轴位，两个不对称配位的双齿羧酸盐配体的O原子为在赤道平面上。二丁基双（E）-2-羟基-5-（[（3-甲基苯基）二氮烯基]苯并]}锡（IV）环己烷半溶剂化物[Sn（C 4 H 9）2（C 14 H 11 N 2 ö 3）2 ]·0.5C 6 H 12，（I），二苄基双（E）−5 [[（4-溴苯基）二氮烯基] -2-羟基苯甲酰基}锡（IV），[Sn（C 7 H 7）2（ C 13 H 8 BrN 2 O 3）2 ]，（II）和水合苄基双（4-（（E）‐ [（Z）‐4-羟基戊-3-3‐2‐亚基]氨基}苯并）锡（IV ）苯二溶剂化物，[Sn（C 7 H 7）2（C 12 H 12 NO 3）2（H
• Dibutyltin(IV) complexes of the 5-[(E)-2-(Aryl)-1-diazenyl]-2-hydroxybenzoic acid ligand: an investigation of structures by X-ray diffraction, solution and solid state tin NMR, electrospray ionisation MS and assessment of in vitro cytotoxicity
  作者：Tushar S. Basu Baul、Wandondor Rynjah、Rudolph Willem、Monique Biesemans、Ingrid Verbruggen、Michal Holèapek、Dick de Vos、Anthony Linden

  DOI：10.1016/j.jorganchem.2004.07.050

  日期：2004.12

  A series of dibutylbis5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoato}tin(IV) complexes, Bu2Sn(LH)2, have been prepared and characterized by 1H, 13C, 119Sn NMR and ESI mass spectrometry in solution. The structures of the complexes Bu2Sn(L1H)2 (1), Bu2Sn(L3H)2 (3), Bu2Sn(L4H)2 (4), and Bu2Sn(L6H)2 (6) (L = 5-[(E)-2-(aryl)-1-diazenyl]-2-hydroxybenzoate: aryl = phenyl (L1H), 3-methylphenyl (L3H), 4-methylphenyl

  已制备了一系列二丁基双5-[（E）-2-（芳基）-1-二氮烯基] -2-羟基苯并氨基}锡（IV）配合物Bu 2 Sn（LH）2，其特征在于1 H，溶液中的13 C，119 Sn NMR和ESI质谱。配合物Bu 2 Sn（L 1 H）2（1），Bu 2 Sn（L 3 H）2（3），Bu 2 Sn（L 4 H）2（4）和Bu 2 Sn（L）的结构6小时）2（6）（L = 5-[（E）-2-（芳基）-1-二氮烯基] -2-羟基苯甲酸酯：芳基=苯基（L 1 H），3-甲基苯基（L 3 H），4-甲基苯基（L通过X射线晶体学和固态的117 Sn CP-MAS NMR光谱测定4 H）和4-溴苯基（L 6 H））。通常，发现该络合物在锡原子周围采用斜梯形双锥体排列。此外，在配合物1和3中，桥接的分子间Sn⋯O接触较弱，而在配合物4和6中则没有。，其中来自相邻分子的一个羟基氧原子与Sn原子的配位较弱，从
• 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
  作者：Tushar S. Basu Baul、Wandondor Rynjah、Eleonora Rivarola、Claudio Pettinari、Michal Holčapek、Robert Jirásko、Ulli Englert、Anthony Linden

  DOI：10.1016/j.jorganchem.2007.04.044

  日期：2007.8

  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.
• US8735445B2
  申请人：——

  公开号：US8735445B2

  公开（公告）日：2014-05-27