2,4,6-trimethyl-N-(5,6,7-trihydroquinolin-8-ylidene)phenylamine | 1263563-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2,4,6-trimethyl-N-(5,6,7-trihydroquinolin-8-ylidene)phenylamine
• 英文别名: N-(2,4,6-trimethylphenyl)-6,7-dihydro-5H-quinolin-8-imine
• CAS: 1263563-73-0
• 化学式: C₁₈H₂₀N₂
• 分子量: 264.37
• InChiKey: URSMCRHHOSDZMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  氯化镍二甲氧基乙烷 、 2,4,6-trimethyl-N-(5,6,7-trihydroquinolin-8-ylidene)phenylamine 以 乙醇 为溶剂， 反应 12.0h， 生成 2,4,6-trimethyl-N-(5,6,7-trihydroquinolin-8-ylidene)phenylaminonickel(II) dichloride
  参考文献：
  名称：

  通过借位氢或脱氢​​缩合反应，以几何学受限的亚氨基吡啶基镍催化的胺或亚胺的合成

  摘要：

  报道了使用双齿几何约束的亚氨基吡啶基镍配合物作为催化剂，通过借入氢用醇对各种苯胺与醇的有效的Ni催化的N-烷基化。取代的苄醇和短/长链脂族醇可以用作烷基化源，与芳族和杂芳族胺偶联，以中等至极好的收率得到各种N-烷基化结果。镍催化体系也适用于脂肪族胺，可通过无受体脱氢缩合策略选择性地输送相应的亚胺。

  DOI：

  10.1016/j.tetlet.2020.152604
• 作为产物：
  描述：

  6,7-二氢-5H-喹啉-8-酮 、 2,4,6-三甲基苯胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 2,4,6-trimethyl-N-(5,6,7-trihydroquinolin-8-ylidene)phenylamine
  参考文献：
  名称：

  通过借位氢或脱氢​​缩合反应，以几何学受限的亚氨基吡啶基镍催化的胺或亚胺的合成

  摘要：

  报道了使用双齿几何约束的亚氨基吡啶基镍配合物作为催化剂，通过借入氢用醇对各种苯胺与醇的有效的Ni催化的N-烷基化。取代的苄醇和短/长链脂族醇可以用作烷基化源，与芳族和杂芳族胺偶联，以中等至极好的收率得到各种N-烷基化结果。镍催化体系也适用于脂肪族胺，可通过无受体脱氢缩合策略选择性地输送相应的亚胺。

  DOI：

  10.1016/j.tetlet.2020.152604

文献信息

• Geometry Constrained N-(5,6,7-Trihydroquinolin-8-ylidene)arylaminopalladium Dichloride Complexes: Catalytic Behavior toward Methyl Acrylate (MA), Methyl Acrylate-co-Norbornene (MA-co-NB) Polymerization and Heck Coupling
  作者：Yanning Zeng、Qaiser Mahmood、Tongling Liang、Wen-Hua Sun

  DOI：10.3390/molecules21121686

  日期：——

  A new pair of plladium complexes (Pd4 and Pd5) ligated with constrained N-(5,6,7-trihydroquinolin-8-ylidene)arylamine ligands have been prepared and well characterized by 1H-, 13C-NMR and FTIR spectroscopies as well as elemental analysis. The molecular structure of Pd4 and Pd5 in solid state have also been determined by X-ray diffraction, showing slightly distorted square planar geometry around the palladium metal center. All complexes Pd1–Pd5 are revealed highly efficient catalyst in methyl acrylate (MA) polymerization as well as methyl acrylate/norbornene (MA/NB) copolymerization. In the case of MA polymerization, as high as 98.4% conversion with high molecular weight up to 6282 kg·mol−1 was achieved. Likewise, Pd3 complex has good capability to incorporate about 18% NB content into MA polymer chains. Furthermore, low catalyst loadings (0.002 mol %) of Pd4 or Pd5 are able to efficiently mediate the coupling of haloarenes with styrene affording up to 98% conversion.

  一对新的铂金配合物（Pd4和Pd5）与受限的N-(5,6,7-三氢喹啉-8-亚基)芳胺配体结合，已成功制备并通过1H-NMR、13C-NMR、FTIR光谱以及元素分析进行充分表征。Pd4和Pd5的固态分子结构也通过X射线衍射确定，显示铂金金属中心周围的方平面几何形状略有扭曲。所有配合物Pd1–Pd5在甲基丙烯酸酯（MA）聚合以及甲基丙烯酸酯/挠烯（MA/NB）共聚合中表现出高效的催化活性。在MA聚合的情况下，转化率高达98.4%，分子量高达6282 kg·mol−1。同样，Pd3配合物在将约18%挠烯纳入MA聚合物链中也具有良好的能力。此外，Pd4或Pd5的低催化剂负荷（0.002 mol%）能够高效催化卤代芳烃与苯乙烯的偶联，转化率高达98%。
• N-(5,6,7-Trihydroquinolin-8-ylidene)arylaminonickel dichlorides as highly active single-site pro-catalysts in ethylene polymerization
  作者：Jiangang Yu、Yanning Zeng、Wei Huang、Xiang Hao、Wen-Hua Sun

  DOI：10.1039/c1dt10541h

  日期：——

  A series of N-(5,6,7-trihydroquinolin-8-ylidene)arylamine ligands was synthesized and fully characterized by NMR, IR spectroscopy and elemental analysis. Dimeric N-(5,6,7-trihydroquinolin-8-ylidene)arylaminonickel dichlorides were prepared and examined by IR spectroscopy and elemental analysis, and the molecular structures of the representative nickel complexes were determined by the single crystal X-ray diffraction. On treatment with various alkylaluminiums, all the title complexes exhibited highly active, single-site active behavior for ethylene polymerization producing polyethylene (PE) waxes. The catalytic systems using the co-catalysts diethylaluminium chloride (Et2AlCl) or methylaluminoxane (MAO) were investigated in detail, and the molecular weights and distributions of the PEs obtained were found to significantly rely on the nature of the different ligands present and reaction parameters such as the molar ratios of Al/Ni, reaction temperature and reaction time.

  合成了一系列 N-(5,6,7-三氢喹啉-8-亚基)芳胺配体，并通过核磁共振、红外光谱和元素分析对其进行了全面表征。制备了二聚 N-(5,6,7-三氢喹啉-8-亚基)芳基胺二氯化镍，并通过红外光谱和元素分析对其进行了检测，还通过单晶 X 射线衍射测定了代表性镍配合物的分子结构。用各种烷基铝处理后，所有标题配合物在乙烯聚合生成聚乙烯（PE）蜡的过程中都表现出高活性、单位活性行为。对使用二乙基氯化铝（Et2AlCl）或甲基铝氧烷（MAO）辅助催化剂的催化体系进行了详细研究，发现所获得的聚乙烯的分子量和分布在很大程度上取决于不同配体的性质以及反应参数，如铝/镍的摩尔比、反应温度和反应时间。
• (Co-)polymerization of methylacrylate with NBE/1-hexene by (8-arylimino-5,6,7-trihydroquinolyl)(methyl)palladium chlorides: an approaching mechanism and the polymeric microstructures
  作者：Yanning Zeng、Qaiser Mahmood、Tongling Liang、Wen-Hua Sun

  DOI：10.1039/c6nj04019e

  日期：——

  analysis. The solid state structures of representative complexes Pd3 and Pd4 were unambiguously confirmed by single crystal X-ray diffraction showing a slightly distorted square planar geometry around the palladium metal center. All these complexes have been found to be highly robust catalyst systems showing high catalytic activities toward the homopolymerization of methyl acrylate at elevated temperature

  一系列甲基化氯化钯N-（5,6,7-三氢喹啉-8-亚烷基）芳基氨基PdMeCl（8-（ArN）-C 9 H 9 NPdMeCl，Ar = 2,6-Me 2 Ph，Pd1 ; 2 1,6-Et 2 Ph，Pd2 ; 2,6-iPr 2 Ph，Pd3 ; 2,4,6-Me 3 Ph，Pd4 ; 2,6-Et 2 -4-MePh，Pd5）通过1 H NMR，13 C NMR，FTIR光谱和元素分析进行表征。代表性配合物Pd3和Pd4的固态结构单晶X射线衍射清楚地证实了这些元素，显示出围绕钯金属中心的正方形平面几何形状略有扭曲。已经发现所有这些络合物都是高度鲁棒的催化剂体系，显示出在升高的温度（100℃）下对丙烯酸甲酯的均聚具有高催化活性，并且产生了分子量高达4121kg mol -1的PMA 。此外，Pd3配合物具有良好的能力，可将降冰片烯（8.5％）和1-己烯（12.7％）掺入MA聚合物链中。