2-((2,6-diethylphenylimino)methyl)quinolin-8-ol | 1272520-18-9

• 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-diethylphenylimino)methyl)quinolin-8-ol
• 英文别名: 2-[(2,6-Diethylphenyl)iminomethyl]quinolin-8-ol
• CAS: 1272520-18-9
• 化学式: C₂₀H₂₀N₂O
• 分子量: 304.392
• InChiKey: CODOCDAOPQNOHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-((2,6-diethylphenylimino)methyl)quinolin-8-ol 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以88%的产率得到2-[(2,6-Diethylanilino)methyl]quinolin-8-ol
  参考文献：
  名称：

  Syntheses, Characterization, and Ethylene Polymerization of Titanium Complexes with Double-Duty Tridentate [ONN] Ligands

  摘要：

  A series of titanium complexes containing the tridentate [CNN] ligands La-Lf were synthesized and characterized. The ligands Lb (8-quinolinolato-CH2NHAr; Ar = 2,6-dasopropylphenyl) has been prepared by the reduction of the corresponding imino-quinolinol compound La (8-quinolinolato-CH=NAr; Ar = 2,6-diisopropylphenyl) with LiAlH4 in high yield. Ligands Lc-Lf were synthesized by a procedure similar to that used to prepare ligand Lb. Reaction of TiCl4 with imino-quinolinol ligand La affords the six-coordinate trichloride titanium complex 1. The selective synthesis of tri- and dichlorotitanium complexes containing ligand Lb was achieved by changing the base for deprotonation. When it is deprotonated by NaH, ligand Lb can be used as a tridentate monoanionic ligand to synthesize trichlorotitanium complex 2. While deprotonated by ''BuLi, it can be used as a tridentate dianionic ligand to synthesize dichlorotitanium complex 3. Other dichlorotitanium complexes 4-7 were synthesized by a procedure similar to that used to prepare complex 3. All complexes have been characterized by H-1 NMR spectra and elemental analysis. The molecular structures of ligand Lb and complex 1 have been characterized by single-crystal X-ray diffraction analyses. XANES and EXAFS spectroscopy performed on the representative complexes 2 and 3 reveals the different coordination geometries. When they are activated by excess methylaluminoxane (MAO), all of the titanium complexes can be used as catalysts for ethylene polymerization and exhibit moderate to good activities. It was found that the catalytic behaviors of the title complexes were highly affected by the coordination entironment of the metal center and the effect of substituent groups on ligands.

  DOI：

  10.1021/om300091e
• 作为产物：
  描述：

  8-羟基喹哪啶 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 26.0h， 生成 2-((2,6-diethylphenylimino)methyl)quinolin-8-ol
  参考文献：
  名称：

  Syntheses, Characterization, and Ethylene Polymerization of Half-Sandwich Zirconium Complexes with Tridentate Imino−Quinolinol Ligands

  摘要：

  A series of half-sandwich zirconium complexes with imino-quinolinol ligands have been synthesized and characterized. The catalytic behaviors of these complexes toward ethylene polymerization were investigated in the presence of methylaluminoxane (MAO) as a cocatalyst. The catalytic behaviors were highly affected by the substituent in both cyclopentadienyl and imino-quinolinol ligands. The Cp analogue complexes CpZr[ONNR]Cl-2 (1a-e) exhibited high activities up to 1.34 x 10(7) g of PE (mol of Zr)(-1) h(-1), whereas the Cp* analogue complexes Cp*Zr[ONNR]Cl-2 (2a-e) also showed moderate activities for ethylene polymerization.

  DOI：

  10.1021/om101059v

文献信息

• Methylaluminium 8-quinolinolates: synthesis, characterization and use in ring-opening polymerization (ROP) of ε-caprolactone
  作者：Wen-Hua Sun、Miao Shen、Wenjuan Zhang、Wei Huang、Shaofeng Liu、Carl Redshaw

  DOI：10.1039/c0dt01207f

  日期：——

  The stoichiometric reactions of 2-(2,6-R-phenylimino)quinolin-8-ol (L1–L5, L1: R = Me, L2: R = Et, L3: R = iPr, L4: R = Cl, L5: R = F) with Me3Al afforded the dimeric aluminium complexes [Me2AlL]2 (1–5) in good yields. By contrast, stoichiometric reactions of 2-(1-(2,6-R-phenylimino)propyl) quinolin-8-ol (L6–L10, L6: R = Me, L7: R = Et, L8: R = iPr, L9: R = Cl, L10: R = F)) with Me3Al gave the mononuclear aluminium complexes Me2AlL (6–10) accompanied with by-products of the form Me2AlL·Me3Al (11–15). All methylaluminium complexes were characterized by NMR spectroscopy, elemental analysis, and the molecular structures of complexes 3, 6 and 8 were determined by single-crystal X-ray diffraction. Aluminium compounds 1–5 possessed negligible activity towards the ring-opening polymerization of ε-caprolactone either in the presence or absence of BnOH. In contrast, in the presence of BnOH, the mononuclear aluminium compounds 6–10 could efficiently initiate the ring-opening polymerization of ε-caprolactone; the polymerization proceeded in a living manner.

  2-(2,6-R苯基亚氨基)喹啉-8-醇(L1~L5, L1: R = Me, L2: R = Et, L3: R = iPr, L4: R = Cl, L5: R = F)与Me3Al的化学计量反应以良好收率得到了二聚体铝配合物[Me2AlL]2 (1~5)。相比之下，2-(1-(2,6-R-苯基亚氨基)丙基)喹啉-8-醇(L6~L10, L6: R = Me, L7: R = Et, L8: R = iPr, L9: R = Cl, L10: R = F)与Me3Al的化学计量反应得到了单核铝配合物Me2AlL (6~10)，同时伴随着副产物Me2AlL·Me3Al (11~15)的生成。所有甲基铝配合物均通过NMR光谱、元素分析进行了表征，配合物3、6和8的分子结构由单晶X射线衍射确定。铝化合物1~5对ε-己内酯的开环聚合无论有无BnOH的存在均无活性。相反，在BnOH存在下，单核铝化合物6~10能高效引发ε-己内酯的开环聚合;聚合过程表现出生长方式。
• Chloroyttrium 2-(1-(Arylimino)alkyl)quinolin-8-olate Complexes: Synthesis, Characterization, and Catalysis of the Ring-Opening Polymerization of ε-Caprolactone
  作者：Wenjuan Zhang、Shaofeng Liu、Wenhong Yang、Xiang Hao、Rainer Glaser、Wen-Hua Sun

  DOI：10.1021/om300778g

  日期：2012.12.10

  together with BnOH, the ring-opening polymerization (ROP) of ε-caprolactone (ε-CL) occurred with high efficiency. Depending on conditions, the ROP of ε-CL produced polycaprolactone with narrow molecular distribution and in a living manner. Theoretical studies of the chlorine/CH2SiMe3 and Me3SiCH2/BnO ligand exchange reactions suggest that the replacement of the apical ligands can proceed without significantly

  YCl 3（THF）3与2-（（芳基）甲基）喹啉-8-钾或2-（1-（芳基乙基）乙基）喹啉-8-钾在THF溶液中的化学计量反应得到单核LYCl 2（DMSO） ）2个配合物1 - 5在DMSO中的存在和有代表性的双核配合物6在不存在的DMSO中。所有钇配合物均已通过NMR测量和元素分析以及配合物1和4 – 6的晶体结构进行了全面表征通过单晶X射线衍射确定。这些结构指示围绕钇中心和五边形双锥体几何的配位数7。该复合物均在赤道平面上具有双峰YCl 2部分和一个三齿有机配体。一旦钇预催化剂的反应1 - 6与的LiCH 2的Si（CH 3）3单独或与的LiCH 2的Si（CH 3）3ε-己内酯（ε-CL）与BnOH一起高效地发生了开环聚合（ROP）。根据条件的不同，ε-CL的ROP可以产生分子分布较窄且具有生命力的聚己内酯。对氯/ CH 2 SiMe 3和Me 3 SiCH 2 / BnO配体交换