1-[N-(4-bromophenyl)]aminomethylidene-2(1H)naphthalenone | 178160-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-[N-(4-bromophenyl)]aminomethylidene-2(1H)naphthalenone
• 英文别名: 1-[(4-bromoanilino)methylidene]naphthalen-2-one
• CAS: 178160-03-7
• 化学式: C₁₇H₁₂BrNO
• 分子量: 326.192
• InChiKey: PXQTZPKPPPKRQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-[N-(4-bromophenyl)]aminomethylidene-2(1H)naphthalenone 、 copper(II) acetate monohydrate 以 乙醇 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Two new copper(II) complexes with chelating N,O-type bidentate ligands: Synthesis, characterization, crystal structure and catalytic activity in azide–alkyne cycloaddition reaction

  摘要：

  Tetra-coordinated copper(II) complexes, [CuL2] and [Cu(phox)(2)], were synthesized by reaction of 1-((4-bromophenylimino) methyl) naphthalen-2-ol, HL, and 2-(2'-hydroxyphenyl)-2-oxazoline, Hphox, ligands with copper acetate, respectively. The complexes were characterized using FT-IR spectroscopy, elemental analyses, and their solid state structures were confirmed by single crystal X-ray diffraction. The catalytic activity of the complexes was evaluated in one-pot azide-alkyne cycloaddition (AAC) click reaction in water without need of any additional agent. The [CuL2] complex showed high catalytic activity in this reaction and 1,2,3-triazole derivatives were produced in moderate to good yields. Crown Copyright (C) 2017 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2017.06.046
• 作为产物：
  描述：

  4-溴苯胺 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 5.0h， 生成 1-[N-(4-bromophenyl)]aminomethylidene-2(1H)naphthalenone
  参考文献：
  名称：

  苯基和吡啶-2-基氨基（亚甲基）萘-2（3H）-一的结构研究。取代基对NMR化学位移的影响。

  摘要：

  通过适当的胺与2-羟基萘醛的缩合合成带有苯基和吡啶基的席夫碱。得到这些席夫碱，为有色结晶固体。这些化合物的质子NMR光谱显示出NH质子的双峰，表明这些席夫碱的酮互变异构体。发现含有羟基部分的吡啶基取代的席夫碱对DMSO溶剂中的NH质子表现出最大的低场偏移，这是合理的，因为这两个化合物使用氢键形成了六元和五元环。相应地，由于与胺质子的偶联，还发现席夫碱的烯烃质子为双峰。这些席夫碱表现出热致变色性质。

  DOI：

  10.1002/mrc.2626

文献信息

• Structural investigation on phenyl- and pyridin-2-ylamino(methylene)naphthalen-2(3<i>H</i>)-one. Substituent effects on the NMR chemical shifts
  作者：Taracad K. Venkatachalam、Gregory K. Pierens、Marc R. Campitelli、David C. Reutens

  DOI：10.1002/mrc.2626

  日期：2010.8

  2-hydroxynaphthaldehyde. These Schiff bases were obtained as colored crystalline solids. The proton NMR spectra of these compounds showed a doublet for the NH protons indicating a keto tautomer for these Schiff bases. The pyridyl-substituted Schiff bases containing hydroxyl moiety were found to show the most downfield shift for the NH protons in DMSO solvent, and this was rationalized due to the formation of a

  通过适当的胺与2-羟基萘醛的缩合合成带有苯基和吡啶基的席夫碱。得到这些席夫碱，为有色结晶固体。这些化合物的质子NMR光谱显示出NH质子的双峰，表明这些席夫碱的酮互变异构体。发现含有羟基部分的吡啶基取代的席夫碱对DMSO溶剂中的NH质子表现出最大的低场偏移，这是合理的，因为这两个化合物使用氢键形成了六元和五元环。相应地，由于与胺质子的偶联，还发现席夫碱的烯烃质子为双峰。这些席夫碱表现出热致变色性质。
• Magnetic properties and theoretical calculations of mononuclear lanthanide complexes with a Schiff base coordinated to Ln(III) ion in a monodentate coordination mode
  作者：Hui Yang、Shan-Shan Liu、Yin-Shan Meng、Yi-Quan Zhang、Lin Pu、Xiao-Qi Yu

  DOI：10.1016/j.ica.2019.04.051

  日期：2019.8

  new mononuclear rare earth (RE) complexes [RE(HL)2(NO3)3(CH3OH)] (HL = 1-[N-(4-bromophenyl)]aminomethylidene-2(1H)naphthalenone; RE = Y (1), Dy (2), Er (3)) have been synthesized. The structures of complexes 1–3 were determined by single-crystal X-ray diffraction analyses. Each complex contains two HL ligands which bind to the RE(III) ion in a monodentate coordination mode, three NO3– and one coordinated

  摘要三种新的单核稀土（RE）配合物[RE（HL）2（NO3）3（CH3OH）]（HL = 1- [N-（4-溴苯基）]氨基亚甲基-2（1H）萘； RE = Y（ 1），Dy（2），Er（3））已经合成。配合物1-3的结构是通过单晶X射线衍射分析确定的。每个络合物包含两个以单齿配位模式与RE（III）离子结合的HL配体，三个NO3-和一个配位的甲醇配体，表现出扭曲的三棱柱（D3h）构型。对于复合物2，在1 kOe下可以观察到磁化的缓慢弛豫。进一步的从头算计算表明，地磁易轴的方向与O（HL）-O（HL）的线平行，偏差角为4.29。 °。此外，复数2的地面gz值为19.6858，接近极限值20。但是，配合物3的低基态的gz值严重偏离极限值18，表明轴向各向异性较弱。交流磁化率的进一步测量证实了复合物3的弱磁行为。
• Two new copper(II) complexes with chelating N,O-type bidentate ligands: Synthesis, characterization, crystal structure and catalytic activity in azide–alkyne cycloaddition reaction
  作者：Mojtaba Bagherzadeh、Arshad Bayrami、Reza Kia、Mojtaba Amini、Laurence J. Kershaw Cook、Paul R. Raithby

  DOI：10.1016/j.ica.2017.06.046

  日期：2017.9

  Tetra-coordinated copper(II) complexes, [CuL2] and [Cu(phox)(2)], were synthesized by reaction of 1-((4-bromophenylimino) methyl) naphthalen-2-ol, HL, and 2-(2'-hydroxyphenyl)-2-oxazoline, Hphox, ligands with copper acetate, respectively. The complexes were characterized using FT-IR spectroscopy, elemental analyses, and their solid state structures were confirmed by single crystal X-ray diffraction. The catalytic activity of the complexes was evaluated in one-pot azide-alkyne cycloaddition (AAC) click reaction in water without need of any additional agent. The [CuL2] complex showed high catalytic activity in this reaction and 1,2,3-triazole derivatives were produced in moderate to good yields. Crown Copyright (C) 2017 Published by Elsevier B.V. All rights reserved.