2-(benzo[d]oxazol-2-yl)-4-methylquinoline | 64819-81-4

• 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: 2-(benzo[d]oxazol-2-yl)-4-methylquinoline
• 英文别名: 2-(4'-methyl,2'-quinolyl)benzoxazole；4-methyl-2-(2-benzoxazolyl)quinoline；2-benzooxazol-2-yl-4-methyl-quinoline；2-(4-Methylquinolin-2-yl)-1,3-benzoxazole
• CAS: 64819-81-4
• 化学式: C₁₇H₁₂N₂O
• 分子量: 260.295
• InChiKey: NIVOXJCGRUTNNN-UHFFFAOYSA-N

物化性质

• 熔点：
  137-138 °C(Solv: ligroine (8032-32-4))
• 沸点：
  429.7±33.0 °C(Predicted)
• 密度：
  1.248±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 2-(benzo[d]oxazol-2-yl)-4-methylquinoline 以 甲苯 为溶剂， 以76%的产率得到fac-[tricarbonylrhenium(2-(benzo[d]oxazol-2-yl)-4-methylquinoline)Cl]
  参考文献：
  名称：

  Photophysical properties and computational investigations of tricarbonylrhenium(I)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]L and tricarbonylrhenium(I)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]L derivatives (X=N–CH3, O, or S; L=Cl−, pyridine)

  摘要：

  We report a combined experimental and computational study of new rhenium tricarbonyl complexes based on the bidentate heterocyclic N-N ligands 2-(4-methylpyridin-2-yl)benzo[d]-X-azole (X = N-CH3, O, or S) and 2-(benzo[d]-X-azol-2-yl)-4-methylquinoline (X = N-CH3, O, or S). Two sets of complexes are reported. Chloro complexes, described by the general formula Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]Cl (X = N-CH3, 1; X = 0, 2; X = S, 3) and Re(CO)3[2-(benzo[c -X-azol-2-yl)-4-methylquinoline]Cl (X = N-CH3, 4; X = O, 5; X = S, 6) were synthesized heating at reflux Re(CO)(5)Cl with the appropriate N-N ligand in toluene. The corresponding pyridine set {Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo-X-azole]py}PF6 (X = N-CH3, 7; X = O, 8; X = S, 9) and (Re(CO)(3)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]py)PF6(X = N-CH3, 10; X = O, 11; X = S, 12) was synthesized by halide abstraction with silver nitrate of 1-6 followed by heating in pyridine and isolated as their hexafluorophosphate salts. All complexes have been fully characterized by IR, NMR, electrochemical techniques and luminescence. The crystal structures of I and 7 were obtained by X-ray diffraction. DFT and time-dependent (TD) DFT calculations were carried out for investigating the effect of the organic ligand on the optical properties and electronic structure of the reported complexes. (C) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.11.004
• 作为产物：
  描述：

  苯并恶唑 、 勒皮啶 N-氧化物 在 lithium tert-butoxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以75%的产率得到2-(benzo[d]oxazol-2-yl)-4-methylquinoline
  参考文献：
  名称：

  Base-Promoted Cross-Dehydrogenative Coupling of Quinoline N-Oxides with 1,3-Azoles

  摘要：

  An efficient cross-dehydrogenative coupling of quinoline N-oxides and 1,3-azoles has been developed under external oxidant and metal free conditions. The desired products were isolated in good to excellent yields for 26 examples. This methodology provides a practical pathway to biheteroaryls and features high practicality, high efficiency, and environmental friendliness.

  DOI：

  10.1021/acs.orglett.5b00330

文献信息

• Group IIB metal chloride complexes with some 2-(methylpyridyl or -quinolyl)benz-X-azoles
  作者：M. Massacesi、M. Biddau、G. Devoto、E. Barni、P. Savarino

  DOI：10.1016/s0020-1693(00)82532-3

  日期：1984.2

  Abstract The complexes formed by Zn(II), Cd(II) and Hg(II) chlorides with benzimidazole, benzoxazole and benzothiazole linked to 4-methylpyridine and 4-methylquinoline have been prepared and characterized by chemical analysis, infrared spectra and conductivity data. The coordination behaviour of these ligands toward the metal salts and the stereochemistry of the obtained complexes have been investigated

  摘要制备了由Zn（II），Cd（II）和Hg（II）氯化物与苯并咪唑，苯并恶唑和苯并噻唑与4-甲基吡啶和4-甲基喹啉连接的配合物，并通过化学分析，红外光谱和电导率数据进行了表征。研究了这些配体对金属盐的配位行为和所得配合物的立体化学。
• Barni,E.; Savarino,P., Journal of Heterocyclic Chemistry, 1977, vol. 14, p. 937 - 940
  作者：Barni,E.、Savarino,P.

  DOI：——

  日期：——
• Photophysical properties and computational investigations of tricarbonylrhenium(I)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]L and tricarbonylrhenium(I)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]L derivatives (X=N–CH3, O, or S; L=Cl−, pyridine)
  作者：Andrea Albertino、Claudio Garino、Simona Ghiani、Roberto Gobetto、Carlo Nervi、Luca Salassa、Edward Rosenberg、Ayesha Sharmin、Guido Viscardi、Roberto Buscaino、Gianluca Croce、Marco Milanesio

  DOI：10.1016/j.jorganchem.2006.11.004

  日期：2007.2

  We report a combined experimental and computational study of new rhenium tricarbonyl complexes based on the bidentate heterocyclic N-N ligands 2-(4-methylpyridin-2-yl)benzo[d]-X-azole (X = N-CH3, O, or S) and 2-(benzo[d]-X-azol-2-yl)-4-methylquinoline (X = N-CH3, O, or S). Two sets of complexes are reported. Chloro complexes, described by the general formula Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo[d]-X-azole]Cl (X = N-CH3, 1; X = 0, 2; X = S, 3) and Re(CO)3[2-(benzo[c -X-azol-2-yl)-4-methylquinoline]Cl (X = N-CH3, 4; X = O, 5; X = S, 6) were synthesized heating at reflux Re(CO)(5)Cl with the appropriate N-N ligand in toluene. The corresponding pyridine set Re(CO)(3)[2-(4-methylpyridin-2-yl)benzo-X-azole]py}PF6 (X = N-CH3, 7; X = O, 8; X = S, 9) and (Re(CO)(3)[2-(benzo[d]-X-azol-2-yl)-4-methylquinoline]py)PF6(X = N-CH3, 10; X = O, 11; X = S, 12) was synthesized by halide abstraction with silver nitrate of 1-6 followed by heating in pyridine and isolated as their hexafluorophosphate salts. All complexes have been fully characterized by IR, NMR, electrochemical techniques and luminescence. The crystal structures of I and 7 were obtained by X-ray diffraction. DFT and time-dependent (TD) DFT calculations were carried out for investigating the effect of the organic ligand on the optical properties and electronic structure of the reported complexes. (C) 2006 Elsevier B.V. All rights reserved.
• Base-Promoted Cross-Dehydrogenative Coupling of Quinoline <i>N</i>-Oxides with 1,3-Azoles
  作者：Xiaopei Chen、Xiuling Cui、Fangfang Yang、Yangjie Wu

  DOI：10.1021/acs.orglett.5b00330

  日期：2015.3.20

  An efficient cross-dehydrogenative coupling of quinoline N-oxides and 1,3-azoles has been developed under external oxidant and metal free conditions. The desired products were isolated in good to excellent yields for 26 examples. This methodology provides a practical pathway to biheteroaryls and features high practicality, high efficiency, and environmental friendliness.