N-(3-nitrobenzylidene)pyridin-2-amine | 66385-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-nitrobenzylidene)pyridin-2-amine
• 英文别名: (3-nitro-benzylidene)-pyridin-2-yl-amine；2-(3-Nitro-benzylidenamino)-pyridin；2-Pyridinamine, N-[(3-nitrophenyl)methylene]-；1-(3-nitrophenyl)-N-pyridin-2-ylmethanimine
• CAS: 66385-95-3
• 化学式: C₁₂H₉N₃O₂
• 分子量: 227.222
• InChiKey: UJDGGSJKGFHUBU-UHFFFAOYSA-N

物化性质

• 熔点：
  202-205 °C
• 沸点：
  401.3±25.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-nitrobenzylidene)pyridin-2-amine 、 巯基乙酸 以 苯 为溶剂， 生成 2-(2-nitro-phenyl)-3-pyridin-2-yl-thiazolidin-4-one
  参考文献：
  名称：

  El-Shafei,A.K. et al., Journal of the Indian Chemical Society, 1977, vol. 54, p. 743 - 745

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基吡啶 、 间硝基苯甲醛 以 甲苯 为溶剂， 反应 14.0h， 生成 N-(3-nitrobenzylidene)pyridin-2-amine
  参考文献：
  名称：

  铜（II）介导的炔烃级联氨甲基化/环异构化合成咪唑并[1,2- a ]吡啶。

  摘要：

  探索了单一的铜（II）催化的丙酸酯的三组分级联氨甲基化/环异构化形成咪唑并[1,2- a ]吡啶。开发了一种简单的方法，用于在空气中由Cu（OAc）2水合物催化从苯甲醛，2-氨基吡啶和丙酸酯衍生物实际合成官能化的咪唑并[1,2- a ]吡啶。该方案的特点是具有优异的收率，官能团耐受性，最重要的是具有合成咪唑并[1,2 - a ]吡啶基药物分子（如Alpidem）的适应性。

  DOI：

  10.1021/acs.joc.5b02102

文献信息

• Copper(II)-Mediated Aerobic Synthesis of Imidazo[1,2-<i>a</i>]pyridines via Cascade Aminomethylation/Cycloisomerization of Alkynes
  作者：Irina V. Rassokhina、Valerii Z. Shirinian、Igor V. Zavarzin、Vladimir Gevorgyan、Yulia A. Volkova

  DOI：10.1021/acs.joc.5b02102

  日期：2015.11.6

  A single copper(II)-catalyzed three-component cascade aminomethylation/cycloisomerization of propiolates to form imidazo[1,2-a]pyridines was explored. A straightforward method was developed for the practical synthesis of functionalized imidazo[1,2-a]pyridines from benzaldehydes, 2-aminopyridines, and propiolate derivatives catalyzed by Cu(OAc)2 hydrate in the presence of air. The protocol is marked

  探索了单一的铜（II）催化的丙酸酯的三组分级联氨甲基化/环异构化形成咪唑并[1,2- a ]吡啶。开发了一种简单的方法，用于在空气中由Cu（OAc）2水合物催化从苯甲醛，2-氨基吡啶和丙酸酯衍生物实际合成官能化的咪唑并[1,2- a ]吡啶。该方案的特点是具有优异的收率，官能团耐受性，最重要的是具有合成咪唑并[1,2 - a ]吡啶基药物分子（如Alpidem）的适应性。
• Sarma, Madhushree Das; Ghosh, Subhojit, Journal of the Indian Chemical Society, 2020, vol. 97, # 8, p. 1295 - 1303
  作者：Sarma, Madhushree Das、Ghosh, Subhojit

  DOI：——

  日期：——
• Ultrasonics promoted synthesis of thiazolidinones from 2-aminopyridine and 2-picolilamine
  作者：Daniela P. Gouvêa、Valéria D.O. Bareño、Juliano Bosenbecker、Bruna B. Drawanz、Patrícia D. Neuenfeldt、Geonir M. Siqueira、Wilson Cunico

  DOI：10.1016/j.ultsonch.2012.03.004

  日期：2012.11

  The efficient multicomponent synthesis of thiazolidinones from the reaction of arenealdehydes, mercaptoacetic acid and 2-picolilamine or 2-aminopyridine under ultrasound irradiation are reported. The reaction with 2-aminopyridine needs a Lewis acid catalysis to afford the corresponding 2-aryl-3-(pyridin-2-yl)-1,3-thiazolidin-4-ones. All novel compounds were identified and characterized by H-1 and C-13 NMR spectra. Applying the sonochemical methodology, two series of heterocyclic thiazolidinones were synthesized in good yields after short reaction times. (C) 2012 Elsevier B.V. All rights reserved.
• Luminescent coatings: White-color luminescence from a simple and single chromophore with high anticorrosion efficiency
  作者：Osama Younis、Emad E. El-Katori、Reda Hassanien、Ashraf S. Abousalem、Osamu Tsutsumi

  DOI：10.1016/j.dyepig.2019.108146

  日期：2020.4

  Luminescent coatings have potential commercial applications. Here, the photoluminescence, thermal, and corrosion inhibition properties of reported Schiff bases have been studied. Moreover, quantum chemical calculations have been done to realize the working mechanism of their properties. Interestingly, we succeeded to get a single-chromophore white-color emission from a small Schiff base molecule through a simple technique, where the relative emission intensities at the long and short wavelengths of the visible range were controlled by introducing electron-donating or withdrawing groups. Furthermore, the compounds were found thermally stable and can emit efficiently until 124 degrees C. Also, the electrochemical impedance spectroscopy, electrochemical frequency modulation, Tafel polarization, and surface characterizations have been investigated. The studied compounds showed high inhibition efficiencies (ex. 93%) and played a great role in retarding the stainless-steel corrosion in 2 M H2SO4. These measurements confirmed that the existence of these Schiff bases can reduce the double-layer capacities, corrosion current densities, and corrosion rate simultaneously with increasing the charge transfer resistance values. The studied materials as luminescent coatings may be employed for mixed-type inhibitors and can provide a strategy for the development of new organic materials capable of producing white-color emission from a simple and single molecule.
• El-Shafei,A.K. et al., Journal of the Indian Chemical Society, 1977, vol. 54, p. 743 - 745
  作者：El-Shafei,A.K. et al.

  DOI：——

  日期：——