5-[(E)-2-(3-methylphenyl)-1-diazenyl]quinolin-8-ol | 32903-05-2

• 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: 5-[(E)-2-(3-methylphenyl)-1-diazenyl]quinolin-8-ol
• 英文别名: 5-[(E)-2-(m-tolyl)-1-(diazenyl)]quinolin-8-ol；5-(m-tolyl)azo-8-quinolinol；5-m-tolylazo-quinolin-8-ol；5-m-Tolylazo-chinolin-8-ol
• CAS: 32903-05-2
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: SNNMVOFTYZSZJF-VHEBQXMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.66
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-[(E)-2-(3-methylphenyl)-1-diazenyl]quinolin-8-ol 、 二氯-二(苯基甲基)锡烷 在 sodium methoxide 作用下， 以 甲醇 、 苯 为溶剂， 以33.9%的产率得到cis-bis[5-[(E)-2-(3-methylphenyl)-1-diazenyl]quinolinato]dibenzyltin(IV)
  参考文献：
  名称：

  Dibenzyltin(IV) complexes of the 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-olates: Synthesis and an investigation of structures by X-ray diffraction, solution and solid-state tin NMR, 119Sn Mössbauer and electrospray ionization MS

  摘要：

  A series of cis-bis {5-[(E)-2-(aryl)-1-diazenyl]quinolinolato}dibenzyltin(IV) complexes have been synthesized by reacting sodium salts of 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-ol (LH) and dibenzyltin dichloride. These complexes have been characterized by H-1, C-13, Sn-119 NMR, ESI-MS in solution and by IR and Sn-119m Mossbauer, Sn-117 CP-MAS NMR spectroscopy in solid state. In addition, the structures of three of the dibenzyltin(IV) complexes, viz., Bz(2)Sn(L-2)(2) (2), Bz(2)Sn(L-3)(2) (3), and Bz(2)Sn(L-5)(2) (5) (L = 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-ol: aryl = 4'-methylphenyl- (LH)-H-2), 4'-methoxylphenyl- ((LH)-H-3) and 4-bromophenyl- ((LH)-H-5)) were determined by single-crystal X-ray diffraction. In general, the complexes were found to adopt a distorted cis-octahedral arrangement around the tin atom in both solution and solid state. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.01.065
• 作为产物：
  描述：

  8-羟基喹啉 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 5-[(E)-2-(3-methylphenyl)-1-diazenyl]quinolin-8-ol
  参考文献：
  名称：

  Studies in Azo Dyes. II. Preparation and Bacteriostatic Properties of Azo Derivatives of 8-Quinolinol^1a,b,c

  摘要：

  DOI：

  10.1021/ja01251a067

文献信息

• Studies in Azo Dyes. II. Preparation and Bacteriostatic Properties of Azo Derivatives of 8-Quinolinol^1a,b,c
  作者：R. Norris Shreve、Robert B. Bennett

  DOI：10.1021/ja01251a067

  日期：1943.11
• Basu Baul, T. S.; Sinha, T. K.; Saran, R., Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 1995, vol. 25, p. 615 - 624
  作者：Basu Baul, T. S.、Sinha, T. K.、Saran, R.

  DOI：——

  日期：——
• Diphenyltin(IV) complexes of the 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-olates: Synthesis and multinuclear NMR, 119Sn Mössbauer, electrospray ionization MS, X-ray characterization and assessment of in vitro cytotoxicity
  作者：Tushar S. Basu Baul、Archana Mizar、Antonin Lyčka、Eleonora Rivarola、Robert Jirásko、Michal Holčapek、Dick de Vos、Ulli Englert

  DOI：10.1016/j.jorganchem.2005.09.055

  日期：2006.8

  A series of cis-bis 5-[(E)-2-(aryl)-1-diazenyl]quinolinolato} diphenyltin(IV) complexes have been synthesized and characterized by H-1, C-13, Sn-119 NMR, ESI-MS, IR and Sn-119m Mossbauer spectroscopic techniques in combination with elemental analysis. The structures of a ligand (LH)-H-6 (i.e., 5-[(E)-2-(4-ethoxyphenyl)-1-diazenyl]quinolin-8-ol) and three diphenyltin(IV) complexes, viz., Ph2Sn(L-1)(2)center dot(CH3)(2)CO (1), Ph2Sn(L-4)(2) (4) and Ph2Sn(L-5)(2) (5) (L = 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-ol: aryl = phenyl - ((LH)-H-1); 4'-methylphenyl - ((LH)-H-4) and 4'-bromophenyl - ((LH)-H-5)) were determined by single crystal X-ray diffraction. In general, the complexes were found to adopt a distorted cis-octahedral arrangement around the tin atom. These complexes retain their solid-state structure in non-coordinating solvent as evidenced by Sn-119 NMR spectroscopic results. The in vitro cytotoxicity of 1 is reported and compared with Ph2Sn(OX)(2) (Ox = deprotonated quinolin-8-ol) against seven well characterized human tumor cell lines. (c) 2005 Elsevier B.V. All rights reserved.
• Dibenzyltin(IV) complexes of the 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-olates: Synthesis and an investigation of structures by X-ray diffraction, solution and solid-state tin NMR, 119Sn Mössbauer and electrospray ionization MS
  作者：Tushar S. Basu Baul、Archana Mizar、Xueqing Song、George Eng、Robert Jirásko、Michal Holčapek、Rudolph Willem、Monique Biesemans、Ingrid Verbruggen、Ray Butcher

  DOI：10.1016/j.jorganchem.2006.01.065

  日期：2006.6

  A series of cis-bis 5-[(E)-2-(aryl)-1-diazenyl]quinolinolato}dibenzyltin(IV) complexes have been synthesized by reacting sodium salts of 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-ol (LH) and dibenzyltin dichloride. These complexes have been characterized by H-1, C-13, Sn-119 NMR, ESI-MS in solution and by IR and Sn-119m Mossbauer, Sn-117 CP-MAS NMR spectroscopy in solid state. In addition, the structures of three of the dibenzyltin(IV) complexes, viz., Bz(2)Sn(L-2)(2) (2), Bz(2)Sn(L-3)(2) (3), and Bz(2)Sn(L-5)(2) (5) (L = 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-ol: aryl = 4'-methylphenyl- (LH)-H-2), 4'-methoxylphenyl- ((LH)-H-3) and 4-bromophenyl- ((LH)-H-5)) were determined by single-crystal X-ray diffraction. In general, the complexes were found to adopt a distorted cis-octahedral arrangement around the tin atom in both solution and solid state. (c) 2006 Elsevier B.V. All rights reserved.
• Re-visiting of 5-[(E)-2-(aryl)-1-diazenyl]-quinolin-8-ol with tweaking of Sn–Ph groups: Synthesis, spectroscopic characterization and X-ray crystallography
  作者：Tushar S. Basu Baul、Archana Mizar、Eleonora Rivarola、Ulli Englert

  DOI：10.1016/j.jorganchem.2007.12.032

  日期：2008.5

  Reactions of sodium 5-[(E)-2-(aryl)-1-diazenyl]quinolin-8-olates (LH, where the aryl group is an R-substituted phenyl ring such that for L(1)H: R = H; L(2)H: R = 2'-CH(3); L(3) H: R = 3'-CH(3); L(4)H: R = 4'-CH(3); L(5) H: R = 4'-OCH(3) and L(6) H: R = 4'-OC(2)H(5)) with Ph(3)SnCl in a 1: 1 molar ratio yielded complexes of composition Ph(3)SnL. The complexes have been characterized by (1)H, (13)C , (119)Sn NMR, IR and (119m)Sn Mossbauer spectroscopic techniques in combination with elemental analyses. The crystal structures of Ph(3)SnL(1)center dot 0.5C(6)H(6) (1), Ph(3)SnL(2) (2), Ph(3)SnL(5) center dot C(6)H(6) (5) and Ph(3)SnL(6) center dot 0.5C(6)H(6) (6) were determined. The results of the X-ray studies indicated that the benzene solvated compounds 1, 5 and 6 are distorted square pyramid, with one of the phenyl C atoms in the apex while the ligand arrangement around central Sn atom in 2 is distorted trigonal-bipyramidal, with a phenyl C and the oxinato N atoms in axial positions. (C) 2008 Elsevier B.V. All rights reserved.