2-(2,6-dimethylphenyl)iminomethylquinoline | 24656-79-9

• 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-(2,6-dimethylphenyl)iminomethylquinoline
• 英文别名: 2,6-dimethyl-N-quinolin-2-ylmethylene-aniline；N-(2,6-dimethylphenyl)-1-quinolin-2-ylmethanimine
• CAS: 24656-79-9
• 化学式: C₁₈H₁₆N₂
• 分子量: 260.338
• InChiKey: LDWJKJPCANFJBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,6-dimethylphenyl)iminomethylquinoline 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and Structural Analysis of (Imido)Vanadium(V) Complexes Containing Chelate (Anilido)Methyl-imine Ligands: Ligand Effect in Ethylene Dimerization

  摘要：

  A series of (imido)vanadium dichlorido complexes containing chelate anionic donor ligands of the type, VCl2(L)(NR) [R = 1-adamantyl (Ad), L = 2-(2,6-Me2C6H3)NCH2(C9H6N) (2), 8-(2,6-Me2C6H3)NCH2(C9H6N) (3); L = 2-(2,6-R'2C6H3)NCH2(C5H4N), R = 2-MeC6H4, R' = Me (4a), 'Pr (4b); L = 2-(2,6-Me2C6H3)NCH2(C5H4N), R = 4-MeC6H4 (5), 3,5-Me2C6H3 (6)], have been prepared and identified. The reactions with ethylene by 2,3 in the presence of methylaluminoxane (MAO) afforded a mixture of high molecular weight polyethylene and oligomers. Reactions with ethylene by VCl2[2-(2,6-R'2C6H3)NCH2(C6H4N))(NAd) (1a,b), 4-6 afforded 1-butene with high selectivities (>92%), and the activities by 4a,b are at the same level as those in la,b. The activities by 5,6 were lower than 4a,b and were at the same level of that by VCl2[2-(2,6-Me2C6H3)NCH2(C5H4N)](NPh). These results thus suggest that both the chelate anionic donor and the imido ligands play a role for both the activity and the selectivity.

  DOI：

  10.1021/ic302633y
• 作为产物：
  描述：

  喹啉-2-甲醛 、 2,6-二甲基苯胺 在 对甲苯磺酸 作用下， 生成 2-(2,6-dimethylphenyl)iminomethylquinoline
  参考文献：
  名称：

  酰胺基喹啉铪和锆配合物的合成，改善了乙烯/1-辛烯共聚性能

  摘要：

  已经开发了一种经济高效且直接的路线来合成酰胺喹啉负载的铪和锆配合物。新的 Hf （Hf1–Hf4） 和 Zr （Zr1） 配合物表现出高热稳定性、高活性和优异的 1-辛烯掺入能力，因此已成功用于高温液相聚合制备聚烯烃弹性体 （POE）。有趣的是，在其他相同条件下，Hf 配合物的活性和 1-辛烯掺入都远高于携带相同配体的 Zr 类似物的活性和 1-辛烯掺入，揭示了对催化性能的显着金属中心效应。此外，配体的性质也极大地影响了催化作用，那些具有供电子取代基的配体有利于共聚。特别是，在 120 °C 下，具有 Pr-取代基的 Hf 络合物 （Hf1） 对乙烯/1-辛烯共聚表现出高达 78150 kg（POE）·mol–1（Hf）·h–1 的活性，并产生具有高分子量 （Mw = 20.2 × 104 g·mol–1）、窄分布 （Đ = 2.2） 和 1-辛烯高掺入度 （49.6 mol%） 的 POE。

  DOI：

  10.1021/acs.organomet.4c00037

文献信息

• Imino-quinolyl palladium(II) and platinum(II) complexes: Synthesis, characterization, molecular structures and cytotoxic effect
  作者：William M. Motswainyana、Martin O. Onani、Abram M. Madiehe、Morounke Saibu、Jeroen Jacobs、Luc van Meervelt

  DOI：10.1016/j.ica.2013.02.029

  日期：2013.5

  Imino-quinolyl ligands L1-L5 were synthesized by condensation reaction sand obtained in good yields. Reactions of the ligands with either PdCl2(cod) or K-2[PtCl4] gave the corresponding palladium(II) and platinum(II) complexes 1-10 also in good yields. All the compounds were characterized by elemental analysis, IR, H-1 and C-13 NMR spectroscopy. X-ray crystallography was used to confirm the structures of these compounds. Molecular structures of 3 and 5 showed that the ligands coordinate to the metal center through the two nitrogen atoms, generating a distorted square planar geometry around the palladium atom. The new complexes exhibited remarkable cytotoxic activities against MCF-7 and HT-29 cancer cell lines. (C) 2013 Elsevier B. V. All rights reserved.
• Koeppl, Alexander; Alt, Helmut G., Journal of Molecular Catalysis A: Chemical, 2000, vol. 154, p. 45 - 54
  作者：Koeppl, Alexander、Alt, Helmut G.

  DOI：——

  日期：——
• Synthesis and Structural Analysis of (Imido)Vanadium(V) Complexes Containing Chelate (Anilido)Methyl-imine Ligands: Ligand Effect in Ethylene Dimerization
  作者：Kotohiro Nomura、Atsushi Igarashi、Shohei Katao、Wenjuan Zhang、Wen-Hua Sun

  DOI：10.1021/ic302633y

  日期：2013.3.4

  A series of (imido)vanadium dichlorido complexes containing chelate anionic donor ligands of the type, VCl2(L)(NR) [R = 1-adamantyl (Ad), L = 2-(2,6-Me2C6H3)NCH2(C9H6N) (2), 8-(2,6-Me2C6H3)NCH2(C9H6N) (3); L = 2-(2,6-R'2C6H3)NCH2(C5H4N), R = 2-MeC6H4, R' = Me (4a), 'Pr (4b); L = 2-(2,6-Me2C6H3)NCH2(C5H4N), R = 4-MeC6H4 (5), 3,5-Me2C6H3 (6)], have been prepared and identified. The reactions with ethylene by 2,3 in the presence of methylaluminoxane (MAO) afforded a mixture of high molecular weight polyethylene and oligomers. Reactions with ethylene by VCl2[2-(2,6-R'2C6H3)NCH2(C6H4N))(NAd) (1a,b), 4-6 afforded 1-butene with high selectivities (>92%), and the activities by 4a,b are at the same level as those in la,b. The activities by 5,6 were lower than 4a,b and were at the same level of that by VCl2[2-(2,6-Me2C6H3)NCH2(C5H4N)](NPh). These results thus suggest that both the chelate anionic donor and the imido ligands play a role for both the activity and the selectivity.
• Synthesis of Amido-quinoline Hafnium and Zirconium Complexes with Improved Performances toward Ethylene/1-Octene Copolymerization
  作者：Xingwang Zhang、Mengxue Zhang、Shaofeng Liu、Zhibo Li

  DOI：10.1021/acs.organomet.4c00037

  日期：——

  higher than those by the Zr analogue bearing the same ligand under otherwise identical conditions, revealing a significant metal center effect on catalytic performances. Moreover, the nature of the ligands also greatly influences the catalysis, and those with electron-donating substituents are favorable for copolymerization. In particular, the Hf complex (Hf1) with iPr-substituents shows an activity as high

  已经开发了一种经济高效且直接的路线来合成酰胺喹啉负载的铪和锆配合物。新的 Hf （Hf1–Hf4） 和 Zr （Zr1） 配合物表现出高热稳定性、高活性和优异的 1-辛烯掺入能力，因此已成功用于高温液相聚合制备聚烯烃弹性体 （POE）。有趣的是，在其他相同条件下，Hf 配合物的活性和 1-辛烯掺入都远高于携带相同配体的 Zr 类似物的活性和 1-辛烯掺入，揭示了对催化性能的显着金属中心效应。此外，配体的性质也极大地影响了催化作用，那些具有供电子取代基的配体有利于共聚。特别是，在 120 °C 下，具有 Pr-取代基的 Hf 络合物 （Hf1） 对乙烯/1-辛烯共聚表现出高达 78150 kg（POE）·mol–1（Hf）·h–1 的活性，并产生具有高分子量 （Mw = 20.2 × 104 g·mol–1）、窄分布 （Đ = 2.2） 和 1-辛烯高掺入度 （49.6 mol%） 的 POE。