2,4,6-trimethyl(di-2-pyridylmethylene)aniline | 1233324-25-8

• 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(di-2-pyridylmethylene)aniline
• 英文别名: 1,1-dipyridin-2-yl-N-(2,4,6-trimethylphenyl)methanimine
• CAS: 1233324-25-8
• 化学式: C₂₀H₁₉N₃
• 分子量: 301.391
• InChiKey: YEOPZEMAMOOPKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  38.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-dichlorobis(benzonitrile)palladium(II) 、 2,4,6-trimethyl(di-2-pyridylmethylene)aniline 以 二氯甲烷 为溶剂， 以98%的产率得到(2,4,6-trimethyl-(di-2-pyridylmethylene)aniline)dichloropalladium(II)
  参考文献：
  名称：

  Synthesis, characterization, and applications of novel di-2-pyridyl imine ligands

  摘要：

  Two novel di-2-pyridyl imines, 2,4,6-trimethyl-(di-2-pyridyl methylene)aniline (1) and 2,6-di-isopropyl-(di-2-pyridyl methylene)aniline (2), were prepared through condensation reactions between 2,2'-dipyridyl ketone and 2,4,6-trimethylaniline and 2,6-di-isopropylaniline. They reacted readily with bis(benzonitrile)dichloropalladium(II) to afford palladium imine complexes. The crystal structure of the palladium complex (3) bearing the 2,4,6-trimethyl-(di-2-pyridylmethylene)aniline ligand revealed coordination of a pyridyl group and an imine group to the metal center. The novel ligands were successfully employed in the Suzuki coupling reaction of p-bromoanisole and phenylboronic acid. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2009.10.013
• 作为产物：
  描述：

  2-二吡啶基酮 、 2,6-二异丙基苯胺 在 Amberlyst-15 作用下， 以 甲苯 为溶剂， 以74%的产率得到2,4,6-trimethyl(di-2-pyridylmethylene)aniline
  参考文献：
  名称：

  Synthesis, characterization, and applications of novel di-2-pyridyl imine ligands

  摘要：

  Two novel di-2-pyridyl imines, 2,4,6-trimethyl-(di-2-pyridyl methylene)aniline (1) and 2,6-di-isopropyl-(di-2-pyridyl methylene)aniline (2), were prepared through condensation reactions between 2,2'-dipyridyl ketone and 2,4,6-trimethylaniline and 2,6-di-isopropylaniline. They reacted readily with bis(benzonitrile)dichloropalladium(II) to afford palladium imine complexes. The crystal structure of the palladium complex (3) bearing the 2,4,6-trimethyl-(di-2-pyridylmethylene)aniline ligand revealed coordination of a pyridyl group and an imine group to the metal center. The novel ligands were successfully employed in the Suzuki coupling reaction of p-bromoanisole and phenylboronic acid. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.inoche.2009.10.013

文献信息

• Different coordination modes of dipyridyl ketimine ligands in cationic arene ruthenium complexes
  作者：Mathiyazhagan Ulaganatha Raja、Bruno Therrien、Georg Süss-Fink

  DOI：10.1016/j.inoche.2012.12.006

  日期：2013.3

  2,2'-Dipyridyl-N-arylimines L (L-1 = 2,4,6-trimethyl(di-2-pyridylmethylene)aniline, L-2 = 2,6-diisopropyl(di-2-pyridylmethylene)aniline) react with arene ruthenium dichloride dimer in methanol to give cationic arene ruthenium complexes of the general type [(arene)Ru(eta(2)-N,N-L)Cl](+) (arene = C6H6, p-MeC6H4Pri). Two coordination modes of the chelating ligands N,N-L are observed. In the major isomer, the ketimine nitrogen atom and one of the two pyridine nitrogen atoms are coordinated to ruthenium, while in the minor isomer the two pyridine nitrogen atoms coordinate to the metal center. In the case of L-1, the minor isomer of the p-cymene ruthenium chloro complex could be isolated as the tetrafluoroborate salt and characterized by single crystal X-ray analysis. The molecular structure of the major isomer was determined by X-ray crystallography in the case of the tetraphenylborate salt of the benzene ruthenium chloro derivative. In both structures, the ruthenium atom shows the expected pseudo-tetrahedral coordination geometry. (c) 2012 Elsevier B.V. All rights reserved.