4'-(4-dimethylaminophenyl)-3,2':6',3''-terpyridine | 1373501-47-3

• 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: 4'-(4-dimethylaminophenyl)-3,2':6',3''-terpyridine
• CAS: 1373501-47-3
• 化学式: C₂₃H₂₀N₄
• 分子量: 352.439
• InChiKey: PGLZOGXXPXOMSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.94
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.91
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4'-(4-dimethylaminophenyl)-3,2':6',3''-terpyridine 、 copper(II) acetate monohydrate 以 甲醇 、 二氯甲烷 为溶剂， 反应 336.0h， 以72.7%的产率得到
  参考文献：
  名称：

  One-dimensional copper(II) coordination polymers built on 4′-substituted 4,2′:6′,4″- and 3,2′:6′,3″-terpyridines: Syntheses, structures and catalytic properties

  摘要：

  Divergent ligands containing either 4,2':6',4 ''- or 3,2':6',3 ''-terpyridine domains (1-4) with various 4'-substituents are synthesized. The new ligand 4 was fully characterized by standard spectroscopic and mass spectrometric technique. All ligands were then used to prepare four new copper(II) coordination polymers (5-8) and good quality single crystals were obtained by the layering method. Single crystal X-ray structural analysis reveals that while the structures of compounds 5 and 6 built on 4,2':6',4 '' -ter pyridine ligands feature similar zigzag chains composed of paddle -wheel {Cu-2(mu-OAc)(4)} units, the use of 3,2':6',3 ''-terpyridine ligands bearing various 4'-substituents leads to different coordination polymers 7 and 8 in which the ligands adopt remarkably distinct binding modes. The copper(II) coordination polymers were employed to the catalytic aerobic oxidations of alcohols mediated by TEMPO radical (TEMPO = 2,2,6,6-tetramethylpiperidinyl-1-oxyl) and the results revealed that the polymers display slightly different catalytic activity towards the oxidation of benzylic alcohol under heterogeneous conditions, and compound 8 was observed to catalyze the reaction in water with almost quantitative yield when a base additive is present. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2015.12.042
• 作为产物：
  描述：

  3-乙酰基吡啶 、 对二甲氨基苯甲醛 在 ammonium acetate 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 以50%的产率得到4'-(4-dimethylaminophenyl)-3,2':6',3''-terpyridine
  参考文献：
  名称：

  一种通过协同插烯异头氧化合成三联吡啶的简便方法

  摘要：

  本研究是首次报道在纳米磁性催化剂而不是有害试剂存在下合成三联吡啶。在此，Fe 3 O 4 @O 2 PO 2 (CH 2 ) 2 NH 3 + CF 3 CO 2 −作为具有磁性的可回收纳米催化剂，应用于乙酰吡啶衍生物（2或3或4-异构体）之间的多组分反应)、芳基醛和乙酸铵在常规加热条件下，在没有任何溶剂的情况下。通过合作插烯异头氧化路线，以可接受的产率和短暂的反应时间获得了衍生的三联吡啶。Fe 3 O 4 @O 2 PO 2 (CH 2 ) 2 NH 3 + CF 3 CO 2 -在上述反应中表现出较高的回收和再利用能力。

  DOI：

  10.1039/d0ra04461j

文献信息

• Cobalt(ii) coordination polymers with 4′-substituted 4,2′:6′,4′′- and 3,2′:6′,3′′-terpyridines: engineering a switch from planar to undulating chains and sheets
  作者：Edwin C. Constable、Catherine E. Housecroft、Markus Neuburger、Srboljub Vujovic、Jennifer A. Zampese、Guoqi Zhang

  DOI：10.1039/c2ce06609b

  日期：——

  Two new ligands 4′-(1H-imidazol-4-yl)-4,2′:6′,4′′-terpyridine (3) and 4′-(4-dimethylaminophenyl)-3,2′:6′,3′′-terpyridine (4) are described. Structure determination of 3·CHCl3 reveals the assembly of hydrogen-bonded chains of molecules of 3; the preference for NHimidazole⋯Ntpy over NHimidazole⋯Nimidazole hydrogen bonds is consistent with the relative basicities of the heterocyclic rings. Reactions of Co(NCS)2 with 4′-phenyl-4,2′:6′,4′′-terpyridine (1), 4′-(4-ethynylphenyl)-4,2′:6′,4′′-terpyridine (2) or 3, produce two-dimensional networks. In each, the Co2+ ion is in an octahedral trans-Co(Ntpy)4(NCS)2} environment. [2Co(1)2(NCS)2·5H2O}n] and [Co(3)2(SCN)2·2MeOH}n] exhibit (4,4) nets. In [Co(2)2(NCS)2·0.67C2H4Cl2·MeOH·H2O}n], a (6,3) net is present. In all three coordination networks, there is substantial twisting of the 4,2′:6′,4′′-terpyridine backbone and as a consequence, the dominant packing interactions are not the face-to-face π-stacking of tpy domains that are ubiquitous in many solid-state structures containing metal-bound tpy domains. As a preliminary investigation of the effects of altering the directionality of the donor set in the terpyridine domain, Co(SCN)2 was reacted with ligand 4, and the one-dimensional coordination polymer [Co(4)(MeOH)2(NCS)2}n] was isolated. Ligand 4 adopts a trans,trans-arrangement and the zig-zag chains are undulating. The buckled sheets that result from the intermeshing of the chains contrast with the planar sheets observed in [Cd(5)(OH2)2(ONO2)(O2NO)·H2O}n] (5 = 4′-(4-dimethylaminophenyl)-4,2′:6′,4′′-terpyridine). The observed packing interactions suggest that the change from planar to undulating chains and sheets on going from 5 to 4 is a consequence of optimizing face-to-face π-stacking interactions.

  描述了两种新配体4'-(1H-咪唑-4-基)-4,2':6',4''-三吡啶（3）和4'-(4-二甲氨基苯基)-3,2':6',3''-三吡啶（4）。对3·CHCl3的结构测定显示了3分子通过氢键组装成的链；NH咪唑—Ntpy相较于NH咪唑—N咪唑的氢键偏好与杂环的相对碱性一致。Co(NCS)2与4'-苯基-4,2':6',4''-三吡啶（1）、4'-(4-乙炔基苯基)-4,2':6',4''-三吡啶（2）或3的反应生成二维网络。在每个网络中，Co2+离子处于八面体的反式-Co(Ntpy)4(NCS)2}环境中。[2Co(1)2(NCS)2·5 }n]和[Co(3)2(SCN)2·2MeOH}n]表现出(4,4)网。在[Co(2)2(NCS)2·0.67C2H4Cl2·MeOH·H2O}n]中，存在(6,3)网。在这三种配位网络中，4,2':6',4''-三吡啶的主链有显著扭曲，因此，主要的堆积相互作用不是许多含金属结合三吡啶域的固态结构中普遍存在的面对面π-堆叠。作为对改变三吡啶域中施体方向性的初步研究，将Co(SCN)2与配体4反应，得到了一维配位聚合物[Co(4)(MeOH)2(NCS)2}n]。配体4采用反式、反式排布，锯齿状链条波动不断。这种由于链条相互交错而产生的弯曲片层与[Cd(5)(OH2)2(ONO2)(O2NO)· }n]（5 = 4'-(4-二甲氨基苯基)-4,2':6',4''-三吡啶）中的平面片层形成对比。观察到的堆积相互作用表明，从5到4的变化，由平面链到波动链和片层，是优化面对面π-堆叠相互作用的结果。