p-(dimethylamino)-(2,2-dipicolylamino)benzene | 1292806-63-3

• 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: p-(dimethylamino)-(2,2-dipicolylamino)benzene
• 英文别名: 1-N,1-N-dimethyl-4-N,4-N-bis(pyridin-2-ylmethyl)benzene-1,4-diamine
• CAS: 1292806-63-3
• 化学式: C₂₀H₂₂N₄
• 分子量: 318.421
• InChiKey: XGKGUIAKDIHFBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  32.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cadmium(II) perchlorate 、 p-(dimethylamino)-(2,2-dipicolylamino)benzene 以 二氯甲烷 为溶剂， 以85%的产率得到Cd⁽²⁺⁾*2(C₅H₄NCH₂)2NC₆H₄N(CH₃)2=[Cd((C₅H₄NCH₂)2NC₆H₄N(CH₃)2)2]⁽²⁺⁾
  参考文献：
  名称：

  Electrochemically active phenylenediamine probes for transition metal cation detection

  摘要：

  通过对杂环醛进行还原胺化，有效地制备出了一系列新型四烷基对苯二胺（TAPD）配体。这些电化学活性配体的氧化还原特性在与过渡金属阳离子 Zn2+、Ni2+ 和 Cd2+ 络合时会发生显著变化，从而导致氧化电位发生高达 950 mV 的大幅偏移，具体取决于配体的性质。形成的配合物的金属与配体之比为 1 ∶ 2，113Cd NMR 显示了金属的八面体配位层。所有吡啶衍生物都显示出明显的化学选择性（Zn2+ > Cd2+ > Ni2+）。含噻吩的衍生物对锌阳离子的选择性特别高（Zn2+ ≫ Ni2+、Cd2+）。

  DOI：

  10.1039/c0nj00638f
• 作为产物：
  描述：

  2-氯甲基吡啶盐酸盐 、 N,N-二甲基-对苯二胺 在 sodium hydroxide 、 三乙胺 作用下， 以 水 、 苯 为溶剂， 反应 2.0h， 以14%的产率得到p-(dimethylamino)-(2,2-dipicolylamino)benzene
  参考文献：
  名称：

  Control of peroxyoxalate chemiluminescence by nitrogen-containing ligand quenching: turning off and on by ligand–metal ion host–guest interactions

  摘要：

  The control of peroxyoxalate chemiluminescence (PO-CL) by the coordination of nitrogen-containing ligands and metal cations was investigated. Turning the CL off and on was done by PO-CL using 15-monoazacrown-5-tethered anthracene and alkali metal ions. CL quenching and regeneration was also observed in the separated molecular system of 15-monoazacrown-5 and the fluorophores. CL quenching by a number of ligands bearing dipicolylamino groups was evaluated by these PO-CL reactions and found to be closely related to their oxidation potentials, which is dependent on the Weller rate law for electron exchange and this provides strong support for the existence of the CIEEL PO-CL process. When Zn2+ or Cu2+ are added to the PO-CL system quenched by the ligand, N-[2-(2,2'-dipicolylamino)ethyl]aniline, CL was turned on because the electron donating ability of the ligands was modulated. This was controlled by the coordination of the studied metal ions and, therefore, this system results in CL because of host-guest interactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.078

文献信息

• CN115557994
  申请人：——

  公开号：——

  公开（公告）日：——
• Control of peroxyoxalate chemiluminescence by nitrogen-containing ligand quenching: turning off and on by ligand–metal ion host–guest interactions
  作者：Takayuki Maruyama、Yasuyuki Fujie、Noriyuki Oya、Eisuke Hosaka、Aki Kanazawa、Daisuke Tanaka、Yoshiyuki Hattori、Jiro Motoyoshiya

  DOI：10.1016/j.tet.2011.06.078

  日期：2011.9

  The control of peroxyoxalate chemiluminescence (PO-CL) by the coordination of nitrogen-containing ligands and metal cations was investigated. Turning the CL off and on was done by PO-CL using 15-monoazacrown-5-tethered anthracene and alkali metal ions. CL quenching and regeneration was also observed in the separated molecular system of 15-monoazacrown-5 and the fluorophores. CL quenching by a number of ligands bearing dipicolylamino groups was evaluated by these PO-CL reactions and found to be closely related to their oxidation potentials, which is dependent on the Weller rate law for electron exchange and this provides strong support for the existence of the CIEEL PO-CL process. When Zn2+ or Cu2+ are added to the PO-CL system quenched by the ligand, N-[2-(2,2'-dipicolylamino)ethyl]aniline, CL was turned on because the electron donating ability of the ligands was modulated. This was controlled by the coordination of the studied metal ions and, therefore, this system results in CL because of host-guest interactions. (C) 2011 Elsevier Ltd. All rights reserved.
• Electrochemically active phenylenediamine probes for transition metal cation detection
  作者：Rihab Sahli、Noureddine Raouafi、Khaled Boujlel、Emmanuel Maisonhaute、Bernd Schöllhorn、Christian Amatore

  DOI：10.1039/c0nj00638f

  日期：——

  A novel family of tetraalkyl-p-phenylenediamine (TAPD)-based ligands has been efficiently prepared by reductive amination of heterocyclic aldehydes. The redox properties of these electrochemical active ligands change dramatically upon complexation of the transition metal cations Zn2+, Ni2+ and Cd2+ leading to large oxidation potential shifts of up to 950 mV depending on the nature of the ligand. Complexes with a metal to ligand ratio of 1 ∶ 2 were formed and 113Cd NMR revealed an octahedral coordination sphere of the metal. All pyridyl derivatives show a distinct chemoselectivity (Zn2+ > Cd2+ > Ni2+). The thiophenyl containing derivatives display a particularly high selectivity for zinc cations (Zn2+ ≫ Ni2+, Cd2+).

  通过对杂环醛进行还原胺化，有效地制备出了一系列新型四烷基对苯二胺（TAPD）配体。这些电化学活性配体的氧化还原特性在与过渡金属阳离子 Zn2+、Ni2+ 和 Cd2+ 络合时会发生显著变化，从而导致氧化电位发生高达 950 mV 的大幅偏移，具体取决于配体的性质。形成的配合物的金属与配体之比为 1 ∶ 2，113Cd NMR 显示了金属的八面体配位层。所有吡啶衍生物都显示出明显的化学选择性（Zn2+ > Cd2+ > Ni2+）。含噻吩的衍生物对锌阳离子的选择性特别高（Zn2+ ≫ Ni2+、Cd2+）。