N,N-dimethyl-4-(pyridin-4-yldiazenyl)aniline | 63019-82-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-4-(pyridin-4-yldiazenyl)aniline
• 英文别名: 4-[4-(dimethylamino)phenylazo]pyridine；4-(4-dimethylaminophenylazo)pyridine；4-(4-Dimethylamino-phenylazo)-pyridin；Pyridin-4-azo-4-dimethylanilin；Pyridine, 4-(p-(dimethylamino)phenylazo)-
• CAS: 63019-82-9
• 化学式: C₁₃H₁₄N₄
• 分子量: 226.281
• InChiKey: FUVJXDPEJMGTFG-UHFFFAOYSA-N

物化性质

• 沸点：
  357.89°C (rough estimate)
• 密度：
  1.1761 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  40.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3-溴丙基)三乙基溴化铵 、 N,N-dimethyl-4-(pyridin-4-yldiazenyl)aniline 以 乙腈 为溶剂， 反应 23.0h， 以46%的产率得到
  参考文献：
  名称：

  COMPOUND FOR GENERATING SECOND HARMONIC OF LIGHT, DYE COMPOSITION FOR GENERATING SECOND HARMONIC OF LIGHT, AND CELL EXAMINATION METHOD

  摘要：

  提供了一种产生SHG信号但抑制TPF信号生成的化合物。还提供了一种使用该化合物的细胞检查方法。一种用于产生光的二次谐波的化合物，该化合物是具有式（1）的偶氮苯衍生物，或其盐。（R1和R2独立表示具有6-12个碳原子的烷基基团，R3至R18独立表示从氢、卤素、烷基基团、烷氧基团、芳基、氨基、羟基、硝基和氰基中选择的取代基，但R5和R6、R9和R10、R13和R14以及R17和R18可以结合在一起形成具有5-7个碳原子的环结构。X表示—N+R19R20R21、磺酰基、羧基或—OR基团。这里，R19、R20和R21独立表示具有1-5个碳原子的直链或支链烷基基团，—OR表示由烷氧基终止的一价多聚氧化烷基氧基团。a为0或1，b为0或1，n为1-10的整数。

  公开号：

  US20160116460A1
• 作为产物：
  描述：

  4-氨基吡啶 、 N,N-二甲基苯胺 在 tetrafluoroboric acid 、 sodium nitrite 、 碳酸氢钠 作用下， 生成 N,N-dimethyl-4-(pyridin-4-yldiazenyl)aniline
  参考文献：
  名称：

  NMDA 受体季铵盐光敏拮抗剂的研制

  摘要：

  NMDA 受体在 CNS 的许多生理和病理过程中起着关键作用，这些过程需要开发调节配体。特别是，选择性靶向 NMDA 受体的光开关化合物对于分析受体对各种过程的贡献特别有用。最近，我们鉴定了含偶氮苯的季铵化合物 DENAQ（二乙胺-偶氮苯-季铵）和 DMNAQ（二甲胺-偶氮苯-季铵）的光依赖性抗 NMDA 活性。在这里，我们开发了一系列基于 DENAQ 结构的光敏化合物，并使用膜片钳方法研究了它们对大鼠脑神经元谷氨酸受体的作用。我们发现化合物的活性和光照的影响在很大程度上取决于结构细节，因为即使是微小的结构修改也会极大地改变活性和对光照的敏感性。化合物 PyrAQ（吡咯烷-偶氮苯-季铵）是最活跃的，对 NMDA 受体产生快速和完全可逆的抑制作用。集成电路环境光和单色光条件下的50值分别为 2 和 14 μM。抗 AMPA 活性要弱得多。PyrAQ 的作用不依赖于 NMDA 受体活性、激动剂

  DOI：

  10.1016/j.ejphar.2022.175448

文献信息

• Transition Metal Complexes with Bidentate Ligands Spanningtrans-Positions. XII. Steric effects in the kinetics and mechanism of substitutions at hydride and methyl bisphosphine platinum (II) complexes
  作者：Lars I. Elding、Bruno Kellenberger、Luigi M. Venanzi

  DOI：10.1002/hlca.19830660607

  日期：1983.9.21

  Ligand substitution reactions on square-planar platinum (II) complexes of the types trans-[PtRXL2], trans-[PtR(4-PADA)L2][BF4], trans-[PtRX(

  配体上正方形平面铂取代反应（II）的种类的复合物的反式- [PtRXL 2 ]，反式- [PTR（4- PADA）L- 2 ] [BF 4 ]，反式- [PtRX（
• Photoswitchable and pH responsive organoplatinum(<scp>ii</scp>) complexes with azopyridine ligands
  作者：Mohamed E. Moustafa、Matthew S. McCready、Paul D. Boyle、Richard J. Puddephatt

  DOI：10.1039/c7dt01290j

  日期：——

  Several platinum(II) complexes with ligands containing azo groups have been prepared and structurally characterised, and their photoswitching between trans and cis azo group isomers has been studied. The azo groups in the cationic complexes [PtMe(bipy)(4-NC5H4-N=N-4-C6H4X][PF6], X = H, OH or NMe2, and in the dicationic complex [Pt(bipy)(4-H2NC6H4-N=N-C6H5)2][OTf]2 undergo trans to cis photoswitching

  已经制备了几种具有含偶氮基团的配体的铂（II）配合物，并对其结构进行了表征，并且研究了它们在反式和顺式偶氮基团异构体之间的光开关。阳离子配合物[PtMe（bipy）（4-NC5H4-N = N-4-C6H4X] [PF6]，X = H，OH或NMe2和偶氮配合物[Pt（bipy）（4- H2NC6H4-N = N-C6H5）2] [OTf] 2在365 nm辐照下进行顺式到顺式光转换，复合物[PtMe（bipy）（4-NC5H4-N = N-4-C6H4NMe2] [PF6]也显示出对质子化具有可逆的盐致变色作用，从而得到二价络合物[PtMe（bipy）（4-NC5H4-NH = N-4-C6H4NMe2] 2+。铂（II）络合物中前沿轨道的性质取决于电荷金属-配体键的复杂度和程度。
• Structural Arrangement of 4‐[4‐(Dimethylamino)phenylazo]pyridine Push–Pull Molecules in Acidic Layered Hosts Solved by Experimental and Calculation Methods
  作者：Klára Melánová、Petr Kovář、Martina Gamba、Miroslav Pospíšil、Ludvík Beneš、Vítězslav Zima、Jan Svoboda、David Miklík、Filip Bureš、Petr Knotek

  DOI：10.1002/ejic.201601053

  日期：2017.1.3

  molecules. Dehydration of this intercalate leads to disturbing of their arrangement, mainly in the case of protonated guest molecules. In the case of dehydrated γ-ZrP, the guest molecules are head-to-tail ordered and the guest molecules in the hydrated form of γ-ZrP are more disordered than in the dehydrated intercalate. The simulations also described a layer shift present in the dehydrated γ-ZrP intercalate

  4-[4-(N,N-二甲氨基)苯基偶氮]吡啶（进一步表示为G）代表一种推拉分子，可以插入磷酸锆（α-ZrP和γ-ZrP）和4-磺基苯基膦酸锆中(ZrSPP)。对于α-ZrP·0.2G·1.5H2O、γ-ZrP·0.2G·1.5H2O和ZrSPP·0.5G·1H2O，所获得的插层形成单相，层间距分别为12.75、16.31和24.11 A。插层时层间距离的增加表明插层客体的分子与主体层平行。所有的插层都通过红外和紫外-可见光谱进一步表征。层间空间中的客体排列是通过分子模拟方法获得的。在水合和脱水 α-ZrP 和 γ-ZrP 插层模型中，分别对质子化和非质子化形式的客体进行计算。在 α-ZrP 嵌入的情况下，层间水的存在稳定了客体分子的头尾排列。这种嵌入物的脱水会扰乱它们的排列，主要是在质子化客体分子的情况下。在脱水 γ-ZrP 的情况下，客体分子是头对尾有序的，γ-ZrP 水合形式的客体分子比脱水嵌入物更无序。模拟还描述了脱水的
• Molecular Design of Boronic Acid-Based Dye Receptors for Nucleosides
  作者：Masayuki Takeuchi、Masahiro Taguchi、Hideyuki Shinmori、Seiji Shinkai

  DOI：10.1246/bcsj.69.2613

  日期：1996.9

  Chromophric receptors for nucleosides were designed utilizing the boronic acid–diol interaction which effectively operates in aqueous solution. Receptors consist of a boronic acid moiety and a dimethylaminophenylazo moiety. The boronic acid moiety forms a covalently-bonded ester linkage with the 2,3-diol group in nucleosides in a reversible manner and the anionic charge generated on the boron atom is stabilized intramolecularly by the pyridinium cation. The azo moiety can overlap with the heteroaromatic ring moiety in nucleosides to stabilize the complex. The complexation constants could be conveniently determined by the absorption spectral change. Comparison of the complexation constants with those of 2-deoxyadenosine without 2-OH and 1,4-anhydroerythritol without the heteroaromatic ring established that the complex formation is primarily due to the boronic acid–diol (2,3-diol) interaction and secondarily facilitated by the hydrophobic and/or π–π stacking interactions.

  核苷的发色受体是利用硼酸-二醇相互作用设计的，该相互作用在水溶液中有效地起作用。受体由硼酸部分和二甲氨基苯基偶氮部分组成。硼酸部分以可逆的方式与核苷中的2,3-二醇基团形成共价键合的酯键，并且硼原子上产生的阴离子电荷通过吡啶鎓阳离子在分子内稳定。偶氮部分可以与核苷中的杂芳环部分重叠以稳定复合物。通过吸收光谱的变化可以方便地确定络合常数。与不含 2-OH 的 2-脱氧腺苷和不含杂芳环的 1,4-脱水赤藓糖醇的络合常数的比较表明，络合物的形成主要是由于硼酸-二醇（2,3-二醇）相互作用，其次是促进通过疏水性和/或π-π堆积相互作用。
• Synthesis, structures and optical properties of coordination compounds bearing N,N-dimethyl-4-(pyridin-4-yldiazenyl) aniline
  作者：Ling-Yun Xu、Hong-Xia Chen、Xue-Jian Sun、Pei-Yang Gu、Jian-Feng Ge、Na-Jun Li、Qing-Feng Xu、Jian-Mei Lu

  DOI：10.1016/j.poly.2011.12.029

  日期：2012.3

  Seven coordination compounds, [Zn(Dpya)SO4(H2O)(3)](n) (1,1D chain), [Cu(Dpya)SO4(H2O)(3)](n) (2, 1D chain), [MpOS(3)(Dpya)(2)Cu3I](n) (3, 1D chain), [Cu(Dpya)I](n) (4, 1D chain), [Zn(Dpya)(NO3)(2)](n), (5, dimer), [Cu(Dpya)(Ac)(2)](n) (6. dimer), [Zn(Dpya)(2)Cl-2](n) (7, mononuclear) (Dpya = N,N-dimethy1-4-(pyridin-4-yldiazenyl) aniline) were synthesized and characterized by FTIR, elemental analysis and TG analysis. The structures of all these compounds were determined by single crystal X-ray diffraction, and structural analysis reveals that compounds 1-4 are 1D coordination polymers, compounds 5 and 6 are dimers with a similar structure and compound 7 is a mononuclear complex. The structural construction of these compounds is affected not only by the metal centers but also by the different counteranions. The photophysical properties of the ligand and the coordination compounds were also studied. For example, the third-order nonlinear optical (NLO) properties of the ligand and its coordination compounds were measured by a 532 nm laser using the Z-scan technique. The ligand Dpya and three coordination compounds (1, 2 and 4) show non-linear reversible saturated absorption (RSA) behavior. More interestingly, the ligand Dpya shows visible green luminescence (). 520 nm). The luminescent property was tuned by different metal ions and structures. It should be noted that compound 1 exhibits a strong orange-light emission assigned to a ligand-metal charge transfer (LMCT). (C) 2012 Elsevier Ltd. All rights reserved.