N-(2-pyridylmethylene)benzene-1,4-diamine | 872408-06-5

• 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-(2-pyridylmethylene)benzene-1,4-diamine
• 英文别名: 4-(pyridin-2-ylmethylideneamino)aniline
• CAS: 872408-06-5
• 化学式: C₁₂H₁₁N₃
• 分子量: 197.239
• InChiKey: SHYIJZVXBODCRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 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：
  51.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  五羰基溴化锰(I) 、 N-(2-pyridylmethylene)benzene-1,4-diamine 以 丙酮 为溶剂， 以87%的产率得到
  参考文献：
  名称：

  绿光诱导的PhotoCORM：对MnI和ReI羰基配合物的溶菌酶结合亲和力和生物活性评估

  摘要：

  的反应ñ -与（2-吡啶基亚甲基）苯-1,4-二胺（L）[MBR（CO）5 ]（M =锰我和再我），得到式[MBR（CO）的配合物3 L] [ M ＝ Mn I（1）和Re I（2）]。配合物1在525–468 nm范围内的光照下会释放出CO。从2中未检测到光诱导的CO释放。通过溴化物的配体交换获得的反应性叠氮化物络合物3与贫电子炔烃二甲基乙炔二羧酸酯反应生成三唑酸酯络合物4（[Mn（triazolate COOMe，COOMe）（CO）3 L]）通过游离催化剂[3 + 2]环加成偶联。复合物1对白色念珠菌和新型隐球菌具有令人感兴趣的抗真菌活性（MIC = 30 nM），对非癌性人胚肾细胞的杀伤活性为12.56 µg / mL 。通过电喷雾电离质谱研究复合物对鸡蛋清溶菌酶的反应性。

  DOI：

  10.1002/ejic.201801055
• 作为产物：
  描述：

  吡啶-2-甲醛 、 对苯二胺 以 乙醇 为溶剂， 反应 1.5h， 以76%的产率得到N-(2-pyridylmethylene)benzene-1,4-diamine
  参考文献：
  名称：

  Crystal Structure of N-(2-Pyridylmethylene)benzene-1,4-diamine

  摘要：

  通过 X 射线衍射分析，确定了含氨基希夫碱 N-(2-吡啶亚甲基)苯-1,4-二胺的晶体结构。标题化合物在正方晶系中结晶，空间群为 Pc2 1 n，单胞尺寸为 a = 5.8945 (6)，b = 11.9233 (10)，c = 14.分子通过分子间 N-H-N 氢键连接，形成沿 bc 晶体平面的超分子片。晶体结构通过 C-H---π 堆叠作用进一步稳定。

  DOI：

  10.1007/s10870-011-0120-9

文献信息

• A novel <scp>water‐dispersible</scp> and magnetically recyclable nickel nanoparticles for the one‐pot <scp>reduction‐Schiff</scp> base condensation of nitroarenes in pure water
  作者：Pouya Ghamari Kargar、Asiye Ravanjamjah、Ghodsieh Bagherzade

  DOI：10.1002/jccs.202100172

  日期：2021.10

  electron microscopy (FESEM) analyses. From the satisfactory results obtained from the reduction of nitrogen, this catalytic system is used for a one-pot protocol containing a reduction-Schiff base concentration of diverse nitroarenes. It was corroborated with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from nitroarenes and aldehydes. Finally, the novel Ni-Fe3O4@Pectin~PPA ~ Piconal

  在这项工作中，首先合成了一种称为 Ni-Fe 3 O 4 @Pectin~PPA~Piconal的多相纳米催化剂，并将其作为含有镍官能团的双功能催化剂进行研究。另一方面，这种 Ni-Fe 3 O 4 @Pectin~PPA ~ Piconal 催化剂在水性溶剂中在环境温度下对与硼氢化钠的硝基芳烃还原反应显示出非常有效的性能，其中 NaBH 4被认为是还原剂。这是一种新型磁性催化剂，已通过多种方法批准，包括傅里叶变换红外光谱 (FT-IR)、X 射线粉末衍射 (XRD)、动态光散射 (DLS)、透射电子显微镜 (TEM)、振动样品磁力计 (VSM)、电感耦合等离子体 (ICP)、能量色散 X 射线光谱 (EDX) 和场发射扫描电子显微镜 (FESEM) 分析。根据从氮还原中获得的令人满意的结果，该催化系统用于包含多种硝基芳烃的还原希夫碱浓度的一锅法。硝基芳烃和醛类一锅串联合成亚胺的多相催化实验证实了这一点。最后，新型Ni-Fe
• Intramolecular amide→imine reduction in higher valent rhenium complexes stabilized by arylimido coligand: Rate studies and effect of reductants
  作者：Jaydip Gangopadhyay、Suparna Banerjee、Jiu-Tong Chen、Can-Zhong Lu

  DOI：10.1016/j.poly.2009.04.040

  日期：2009.8

  The present work deals with the imidorhenium(V) complexes of type [ReCl3(NC6H4Y-p)(L)], with Y = OCH3(1d), CH3(1c), H(1b), Cl(1a) where L is the pyridylimine Schiff base ligand obtained from facile condensation of pyridine-2-carboxaldehyde and p-phenylenediamine. Structural authentication of one representative (1d) reveals meridional disposition of three Cl atoms around the metal center in a distorted octahedral ReCl3N3 coordination environment. Re-N-pyridine bond lying trans to Re NC6H4Y-p motif is lengthened by similar to 0.2 angstrom compared to Re-N-imine bond and is attributed to trans influence of imide nitrogen. The complexes, I are reactive towards dilute aqueous nitric acid furnishing amide bound hexavalent rhenium complexes, 2. Six lines EPR spectra have been recorded for 2 in solution phase at ambient condition (g(iso) similar to 1.945, A(av) similar to 493 G) and magnetic susceptibility measurement indicates strong orbital coupling consistent with one electron paramagnetic nature (similar to 1.45 mu(B)). Re-VI/Re-V responses for 1 appear at higher potential (similar to 0.95 V) that those observed for 2 (similar to 0.12 V). Type 2 complexes are reduced (low Re-VI/Re-V reduction potential, +0.15 V) by N2H5+ and NH3OH+ species under mild condition to regenerate 1. The reduction with N2H5+ is nearly five times faster than NH3OH+. Rate study suggests an associative pathway (Delta H-not equal = 11.61 kcal mol(-1), Delta S-not equal = -31.22 eu using N2H5+ and Delta H-not equal = 10.74 kcal mol(-1), Delta S-not equal = -37.30 eu using NH3OH+) for amide -> imine transformation. No such analogous amide -> imine conversion has yet been achieved in metal free environment, accentuating the exclusive electronic role of variable metal valence. Further, the oxo complex, 6 does not exhibit intramolecular ligand oxidation suggesting decisive electronic role of the coligands (oxo/arylimido) in stabilizing higher metal valence. (C) 2009 Elsevier Ltd. All rights reserved.
• Cd(II), Ni(II), and Co(II) complexes based on a pyridyl–amine Schiff-base ligand: [M(L)2(NO3)]·(NO3) (M = Cd, Ni, Co), cis-[CoL2Cl2]·(C6H6), and [Co(L)3]·(ClO4)2 (CH3CN)2 (H2O) (L = N-(2-pyridylmethylene)benzene-1,4-diamine, (2-py) CH N C6H4NH2)
  作者：Sung Jin Lee、Soon W. Lee

  DOI：10.1016/j.poly.2018.12.003

  日期：2019.2

  A pyridyl-amine Schiff-base compound (L = N-(2-pyridylmethylene)benzene-1,4-diamine) reacted with several metal salts (Cd(NO3)(2)center dot 4(H2O), Ni(NO3)(2)center dot 6(H2O), Co(NO3)(2)center dot 6(H2O), CoCl2 center dot 6(H2O), Co(ClO4)(2)center dot 6(H2O)) to give molecular complexes: [M(L)(2)(NO3)]center dot(NO3) (M = Cd (1), Ni (2), Co (3)), cis-[Co(L)(2)Cl-2] (C6H6) (4), and [Co(L)(3)]center dot(ClO4)(2)center dot(CH3CN)(2)center dot(H2O) (5). Complexes 1-3, whose starting compounds possess NO3- anions, were isostructural octahedral complexes. In complexes 3-5, whose starting compounds have the same metal but different anions, the anions in the products exhibited different coordination modes depending on the identity of the metal. In all complexes, the amine end of the ligand (L) remains uncoordinated. The thermal behavior of the complexes is also described. (C) 2018 Elsevier Ltd. All rights reserved.
• Green‐Light‐Induced PhotoCORM: Lysozyme Binding Affinity towards Mn ^I and Re ^I Carbonyl Complexes and Biological Activity Evaluation
  作者：Ahmed M. Mansour

  DOI：10.1002/ejic.201801055

  日期：2018.12.2

  Reaction of N‐(2‐pyridylmethylene)benzene‐1,4‐diamine (L) with [MBr(CO)5] (M = MnI and ReI) affords complexes of the type [MBr(CO)3L] [M = MnI (1) and ReI (2)]. Complex 1 releases CO upon illumination with light in the range of 525–468 nm. No photo induced CO release is detected from 2. Reactive azide complex 3, obtained by bromide's ligand exchange, reacts with the electron‐poor alkyne dimethyl acetylene

  的反应ñ -与（2-吡啶基亚甲基）苯-1,4-二胺（L）[MBR（CO）5 ]（M =锰我和再我），得到式[MBR（CO）的配合物3 L] [ M ＝ Mn I（1）和Re I（2）]。配合物1在525–468 nm范围内的光照下会释放出CO。从2中未检测到光诱导的CO释放。通过溴化物的配体交换获得的反应性叠氮化物络合物3与贫电子炔烃二甲基乙炔二羧酸酯反应生成三唑酸酯络合物4（[Mn（triazolate COOMe，COOMe）（CO）3 L]）通过游离催化剂[3 + 2]环加成偶联。复合物1对白色念珠菌和新型隐球菌具有令人感兴趣的抗真菌活性（MIC = 30 nM），对非癌性人胚肾细胞的杀伤活性为12.56 µg / mL 。通过电喷雾电离质谱研究复合物对鸡蛋清溶菌酶的反应性。
• Crystal Structure of N-(2-Pyridylmethylene)benzene-1,4-diamine
  作者：Katayoun Marjani、Mohsen Mousavi、Fatemeh Namazian

  DOI：10.1007/s10870-011-0120-9

  日期：2011.10

  The crystal structure of amino containing Schiff base, N-(2-pyridylmethylene)benzene-1,4-diamine, was determined via X-ray diffraction analysis. The title compound crystallizes in orthorhombic system, space group Pc2 1 n, with unit cell dimensions a = 5.8945(6), b = 11.9233 (10), c = 14.5356 (16) Å, V = 1021.59 (18) Å3, Z = 4. The molecules are linked by intermolecular N–H···N hydrogen bonds to form supramolecular sheets along with the bc crystallographic plane. The crystal structure is further stabilized by C–H···π stacking interactions.

  通过 X 射线衍射分析，确定了含氨基希夫碱 N-(2-吡啶亚甲基)苯-1,4-二胺的晶体结构。标题化合物在正方晶系中结晶，空间群为 Pc2 1 n，单胞尺寸为 a = 5.8945 (6)，b = 11.9233 (10)，c = 14.分子通过分子间 N-H-N 氢键连接，形成沿 bc 晶体平面的超分子片。晶体结构通过 C-H---π 堆叠作用进一步稳定。