(2-pyridyl)methylene(α-naphthyl)amine | 64921-11-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2-pyridyl)methylene(α-naphthyl)amine
• 英文别名: N-[((2-pyridyl)methyliden)-α-aminonaphthalene]；N-[(2-pyridyl)methyliden]-1-aminonaphthalene；N-(2-pyridylmethylene)-1-naphthylamine；N-((pyridin-2-yl)methylene)-1-naphthylamine；N-(2-pyridinecarboxaldimine)-1-aminonaphthalene；N-(pyridin-2-ylmethylidene)naphthalen-1-amine；α-naphthyl-(2-pyridylmethylene)amine；2-methenepyridyl-1-aminonaphthalene；N,N-(2-Picoliden)-1-naphthylamin；N-[(2-pyridyl)methylidene]-α-aminonaphthalene；N-[(2-pyridyl)methylene]-α-aminonapthalene；naphthalen-1-yl-pyridin-2-ylmethylene-amine；2-C5H4NCH=NC10H7；α-Naipy；1-Naphthalenamine, N-(2-pyridinylmethylene)-；N-naphthalen-1-yl-1-pyridin-2-ylmethanimine
• CAS: 64921-11-5
• 化学式: C₁₆H₁₂N₂
• 分子量: 232.285
• InChiKey: VBBATYHGUOPKGG-UHFFFAOYSA-N

物化性质

• 熔点：
  43.5 °C
• 沸点：
  423.8±18.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-pyridyl)methylene(α-naphthyl)amine 在 AgNO₃ 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 生成 diiodo-[N-[(2-pyridyl)methyliden]-α-aminonaphthalene]palladium(II)
  参考文献：
  名称：

  Palladium(II) complexes of N-[(2-pyridyl)methyliden]-α(or β)-aminonaphthalene: Single crystal X-ray structure of di-chloro-N-[{(2-pyridyl)methyliden}-β-aminonaphthalene]palladium(II), Pd(β-NaiPy)Cl2, spectra and DFT, TD-DFT study

  摘要：

  Palladium(H) complexes of N-[(2-pyridyl)methyliden]-alpha(or beta)-aminonaphthalene (alpha or beta-NaiPy) are reported in this work. They are spectroscopically characterized along with some mixed ligand complexes, using diimine and azoimine functions. The single crystal X-ray structure of [Pd(N-(2-pyridyl)methyliden-beta-aminonaphthalene)Cl-2] has been determined. Luminescence properties of the complexes exhibit a ligand centered pi-pi* emission. Quantum yields (phi) have been calculated and it has been observed that the complexes of alpha-NaiPy show higher phi values than the complexes of beta-NaiPy. Lifetime measurements suggest bi-exponential decay and the average fluorescence lifetime varies from 1.4 to 6.8 ns. The spectroscopic properties are correlated with DFT and TD-DFT calculations in two complexes, Pd(beta-NaiPY)X-2 (X = Cl, I) and they are compared with the free ligand results. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2007.05.049
• 作为产物：
  描述：

  吡啶-2-甲醛 、 1-萘胺 以 乙醇 为溶剂， 生成 (2-pyridyl)methylene(α-naphthyl)amine
  参考文献：
  名称：

  N-[（2-吡啶基）甲基]-α（或β）-氨基萘的钌（II）-CO配合物：合成，光谱研究，晶体结构，氧化还原性质和DFT计算

  摘要：

  表征和性能的反式- （X） - [RUX 2（CO）2（α/β-NaiPy）]（1，2）（α-NaiPy（一），β-​​NaiPy（b）; X = Cl（上1），I（2））在此工作中进行了描述。通过单晶X射线衍射研究证实了该结构。这些化合物与我的反应3 NO在MeCN已分离单羰基反式- （X） - [RUX 2（CO）（乙腈）（α/β-NaiPy）]（3，4）。该配合物显示出强烈的发射性质。1和2的量子产率（ϕ  = 0.02–0.08）高于3和4（ϕ  = 0.006–0.015）。伏安图显示1和2的Ru（III）/ Ru（II）（1.3-1.5 V）电位比3和4（0.8-0.9 V）高，这可能是由于前者中两个π-酸性CO基团的配合。将复合物的电子光谱和氧化还原性质与使用极化连续谱模型（CPCM）的密度泛函理论（DFT）和时变密度泛函理论（TD-DFT）所得的结果进行了比较。

  DOI：

  10.1016/j.jorganchem.2009.09.017

文献信息

• Discovery and Investigation of Anticancer Ruthenium–Arene Schiff-Base Complexes via Water-Promoted Combinatorial Three-Component Assembly
  作者：Mun Juinn Chow、Cynthia Licona、Daniel Yuan Qiang Wong、Giorgia Pastorin、Christian Gaiddon、Wee Han Ang

  DOI：10.1021/jm500455p

  日期：2014.7.24

  design. We report the optimization and validation of a new combinatorial, metal-based, three-component assembly reaction for the synthesis of a library of 442 Ru–arene Schiff-base (RAS) complexes. These RAS complexes were synthesized in a one-pot, on-a-plate format using commercially available starting materials under aqueous conditions. The library was screened for their anticancer activity, and several

  金属支架的结构多样性使其成为药物设计中传统有机支架的可行替代品。组合化学和多组分反应，再加上高通量筛选，在药物发现中是有用的技术，但很少用于基于金属的药物设计中。我们报告了一种新的组合，基于金属的三组分组装反应的优化和验证，该反应用于合成442 Ru-芳烃席夫碱（RAS）配合物的库。这些RAS复合物是在水相条件下，使用市售的起始原料以一锅一板的形式合成的。筛选该文库的抗癌活性，并鉴定了几种细胞毒性先导化合物。具体地，[（η 6 -1,3,5-三异丙基苯）的RuCl（4-甲氧基N-（2-喹啉基亚甲基苯胺）] Cl（4）在卵巢癌（A2780，A2780cisR），乳腺癌（MCF7）和大肠癌（HCT116，SW480）中显示出低的微摩尔IC 50值。没有p53激活或p53 + / +和p53 – / –细胞之间的IC 50值变化，表明4种以及其他可能的先导化合物可能独立于癌症中经常突变的p53抑癌基因发挥作用。
• Synthesis and in vitro reactivity of <i>cis</i>-dichloro-(pyridin-2-ylcarboxaldimine)platinum(II) complexes with DNA
  作者：Liliya G Nikolcheva、Christopher M Vogels、R Alexandra Stefan、Hanni A Darwish、Stephen J Duffy、Robert J Ireland、Andreas Decken、Robert H Hudson、Stephen A Westcott

  DOI：10.1139/v03-034

  日期：2003.4.1

  Five platinum pyridin-2-ylcarboxaldimine complexes of the type cis-[PtCl₂(2-C₅H₄NCH=NR)] (R = CH₂CH₂OH (1); R = N(CH₂CH₂)₂O (2); R = C₆H₅ (3); R = 1-C₁₀H₇ (4); R = (CH₂)₈CH=CH(CH₂)₇CH₃ (5)) were prepared and their in vitro reactivity towards a 20-base pair (single- and double-stranded) DNA determined using nuclease digest studies and RP-HPLC. Variation of the imine functionality allowed for the design of compounds with different physical and chemical properties. Complexes 1 and 3 showed binding to both single- and double-stranded DNA comparable to that of cisplatin (cis-[PtCl₂(NH₃)₂]). Crystals of 1 were monoclinic, space group P2(1)/n, a = 9.6612 (15), b = 12.9678 (19), c = 9.7004(13) Å, β = 117.73(3)°, Z = 4.Key words: platinum, pyridin-2-ylcarboxaldimines, DNA binding studies.

  五种铂金吡啶-2-基羧醛亚胺配合物cis-[PtCl2(2-C5H4NCH=NR)] (R = OH (1); R = N( )2O (2); R = C6H5 (3); R = 1-C10H7 (4); R = (CH2)8CH=CH( )7CH3 (5)) 被制备，并通过核酸酶消化研究和RP-HPLC测定了它们对20碱基对（单链和双链）DNA的体外反应性。改变亚胺功能团允许设计具有不同物理和化学性质的化合物。配合物1和3显示与单链和双链DNA结合的能力与顺铂（cis-[PtCl2(NH3)2]）相当。配合物1的晶体为单斜晶系，空间群P2(1)/n，a = 9.6612 (15) Å，b = 12.9678 (19) Å，c = 9.7004(13) Å，β = 117.73(3)°，Z = 4。关键词：铂金，吡啶-2-基羧醛亚胺，DNA结合研究。
• Influence of anchoring group numbers in an efficient pyridine-anchor co-adsorbent of pyridinecarboxaldimine substituted aminonaphthalene on the performance of N719 sensitized solar cells
  作者：Yuwei Dong、Liguo Wei、Ruiqing Fan、Yulin Yang、Ping Wang

  DOI：10.1039/c6ra06017j

  日期：——

  The anchoring group numbers in pyridine-anchor co-adsorbent has important effect on the performance of co-sensitized solar cells.

  在吡啶-锚基共吸附剂中的锚定基团数量对共敏化太阳能电池的性能有重要影响。
• Silver(I), Gold(I) and Gold(III)-N-Heterocyclic carbene complexes of naphthyl substituted annelated ligand: Synthesis, structure and cytotoxicity
  作者：Tapastaru Samanta、Rudra Narayan Munda、Gourisankar Roymahapatra、Abhishek Nandy、Krishna Das Saha、Salem S. Al-Deyab、Joydev Dinda

  DOI：10.1016/j.jorganchem.2015.05.049

  日期：2015.8

  imidazolium salt 1-naphthyl-2-pyridin-2-yl-2H-imidazo[1,5-a]pyridin-4-ylium hexafluorophosphate (1·HPF6) and three novel N-heterocyclic carbene complexes (NHCs) [Ag(1)2][PF6] (2), [Au(1)2][PF6] (3), and [Au(1)Cl3] 4 have been synthesized and characterized by different spectroscopic techniques. The solid state structure of 2 has been determined by single crystal X-ray diffraction studies. The complex

  新型环状咪唑鎓盐1-萘-2-吡啶-2--2-基-2 H-咪唑并[1,5- a ]吡啶-4-基六氟磷酸根（1 ·HPF 6）和三种新型N-杂环卡宾配合物（NHC的）将[Ag（1）2 ] [PF 6 ]（2），[金（1）2 ] [PF 6 ]（3）和[AU（1）氯3 ] 4已被合成和表征由不同光谱技术。的固态结构2已经通过单晶X射线衍射研究确定。复杂通过反金属化合成了3，而通过歧化过程获得了配合物4。该复合物的细胞毒性2，3和4进行了测试在体外对非小细胞肺癌（A549），结肠直肠癌（HCT-116）和乳腺腺癌（MCF-7）细胞系。测得的IC 50值表明，Au（I）配合物3比配合物2和4以及顺铂更有效。
• Ruthenium(II) carbonyl complexes with N-[(2-pyridyl)methyliden]-(α/β)-aminonaphthalene: Synthesis, spectroscopic studies and DFT calculation
  作者：Shyamal Kumar Sarkar、Mahendra Sekhar Jana、Tapan Kumar Mondal、Chittaranjan Sinha

  DOI：10.1016/j.molstruc.2012.09.060

  日期：2013.3

  Reaction of RuH(Cl)(CO)(PPh 3 ) 3 with bidentate Schiffs base ligands, N-[(2-pyridyl)methyliden]-α/β-aminonaphthalene ( L 1 / L 2 ) led to the formation of photoluminescence ruthenium carbonyl complexes formulated as [RuCl(CO)(PPh 3 ) 2 (L 1 /L 2 )](PF 6 ) ( 1a / 1b ) and [RuH(CO)(PPh 3 ) 2 (L 1 /L 2 )](PF 6 ) ( 2a / 2b ) [ L 1 = N-[(2-pyridyl)methyliden]-α-aminonaphthalene and L 2 = N-[(2-pyridyl

  摘要 RuH(Cl)(CO)(PPh 3 ) 3 与双齿席夫碱配体N-[(2-吡啶基)亚甲基]-α/β-氨基萘(L 1 / L 2 )反应形成光致发光钌羰基配合物配制成 [RuCl(CO)(PPh 3 ) 2 (L 1 /L 2 )](PF 6 ) ( 1a / 1b ) 和 [RuH(CO)(PPh 3 ) 2 (L 1 /L 2 ) ](PF 6 ) ( 2a / 2b ) [ L 1 = N-[(2-吡啶基)亚甲基]-α-氨基萘和L 2 = N-[(2-吡啶基)亚甲基]-β-氨基萘]。该配合物已通过分析和光谱（IR、UV-Vis 和 1 H NMR）技术进行表征。该配合物在可见光区显示出 MLCT 带，并在室温下发射。循环伏安研究表明，Ru(II)/Ru(III) 准可逆的一个电子氧化对在 0.95-1.15 V 范围内。2a 的单晶 X 射线结构显示出围绕钌原子的扭曲八面体几何形状。DFT