5-[(E)-2-(2-methylphenyl)-1-diazenyl]quinolin-8-ol | 907588-67-4

• 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-(2-methylphenyl)-1-diazenyl]quinolin-8-ol
• 英文别名: 5-[(E)-2-(o-tolyl)-1-(diazenyl)]quinolin-8-ol；5-(o-tolyl)azo-8-quinolinol
• CAS: 907588-67-4
• 化学式: C₁₆H₁₃N₃O
• 分子量: 263.299
• InChiKey: AWCWBBFCPBMIAW-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-(2-methylphenyl)-1-diazenyl]quinolin-8-ol 、 mercury dichloride 以 甲醇 为溶剂， 以65%的产率得到
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  8-羟基喹啉 、 邻甲苯胺 在 盐酸 、 sodium nitrite 作用下， 生成 5-[(E)-2-(2-methylphenyl)-1-diazenyl]quinolin-8-ol
  参考文献：
  名称：

  八面体镍 (II) 配合物与取代的 quinolin-8-olates 和吡啶配体的合成、晶体结构、磁性和抗菌筛选

  摘要：

  摘要 新的镍 (II) 化合物，即。反式-[Ni(LHAQ)2(Py)2]·C6H6 (1), 顺式-[Ni(LHAQ)2(3-MePy)2] (2), 顺式-[Ni(L2−MeAQ)2(3) -MePy)2] (3)，反式-[Ni(L4−MeAQ)2(Py)2]·C6H6 (4)，反式-[Ni(L4−OMeAQ)2(Py)2]·C6H6 (5) , 反式-[Ni(L4−OEtAQ)2(Py)2]·C6H6 (6), 反式-[Ni(L4−BrAQ)2(Py)2]·C6H6 (7) 和反式-[Ni(L4−) ClAQ)2(3-MePy)2]·2(3-MePy) (8)（主要配体：LXAQ = 取代的 5-[(E)-2-(芳基)-1-二氮烯基]喹啉-8-醇盐；二级配体：Py = 吡啶或 3-MePy = 3-甲基吡啶）已合成并通过元素分析、IR、UV-vis 光谱进行表征。还测量了化合物的磁化率。化合物的单晶

  DOI：

  10.1016/j.molstruc.2019.127106

文献信息

• 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.
• 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.