N-((2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl)benzamide | 332174-68-2

• 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-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl)benzamide
• 英文别名: N-((2-hydroxynaphthalen-1-yl)(4-nitrophenyl)-methyl)benzamide；N-[(2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl]-benzamide；N-[(2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl]benzamide；N-[4-nitrophenyl-(2-hydroxynaphthalen-1-yl)-methyl]benzamide；N-[4-nitrophenyl-(2-hydroxynaphthalen-1-yl)methyl]-benzamide；N-[(2-hydroxynaphthalen-1-yl)-p-nitrophenyl-methyl]benzamide；N-[(2-hydroxynaphthalen-1-yl)-(4-nitrophenyl)methyl]benzamide
• CAS: 332174-68-2
• 化学式: C₂₄H₁₈N₂O₄
• 分子量: 398.418
• InChiKey: BGGZYWOTOAUQIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰胺 、 N-((2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl)benzamide 、 2-萘酚 在 SiO₂/SO₃H modified multiwalled carbon nanotubes 作用下， 以 neat (no solvent) 为溶剂， 反应 0.12h， 以98%的产率得到N-[(4-nitrophenyl)-(2-hydroxynaphthalen-1-yl)methyl]acetamide
  参考文献：
  名称：

  Solvent-free synthesis of amidoalkyl naphthols in the presence of MWCNTs@SiO2/SO3H as effective solid acid catalyst

  摘要：

  Multiwalled carbon nanotubes (MWCNTs) were modified with sulfonic acid groups through a new method. In the first step, MWCNTs' surfaces were hydroxylated using KMNO4 as oxidating agent and a surfactant (TPABr). Second, SiO2-coated MWCNTs were prepared through the reaction of hydroxylated CNTs with tetraethyl orthosilicate, and in last step, MWCNTs@SiO2/SO3H was prepared using the reaction of MWCNTs@SiO2 with ClSO3H. Obtained catalyst was used as efficient solid acid catalyst for one-pot three-component condensation reaction of 2-naphthol, benzaldehyde, and amide derivatives to afford the corresponding amidoalkyl naphthols. The reaction was performed under solvent-free conditions and products were obtained in high to excellent yields (80-98%). Prepared solid acid catalyst was characterized using FT-IR, BET, TGA, SEM, and EDX techniques. Presented methodology has several advantages such as simple procedure, excellent yields of products, effective reusable solid acid catalyst, and eco-friendly reaction conditions.

  DOI：

  10.1007/s00706-019-02418-2
• 作为产物：
  描述：

  苯甲酰胺 、 对硝基苯甲醛 、 2-萘酚 在 aluminatesulfonic acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以92%的产率得到N-((2-hydroxynaphthalen-1-yl)(4-nitrophenyl)methyl)benzamide
  参考文献：
  名称：

  Aluminatesulfonic acid: Novel and recyclable nanocatalyst for efficient synthesis of aminoalkyl naphthols and amidoalkyl naphthols

  摘要：

  摘要 在本研究中，开发了一种高效、温和且环保的程序，用于通过醛、2-萘酚和氮源（用于酰胺烷基萘酚的酰胺和用于Betti碱的胺）的一锅三组分缩合制备1-酰胺烷基-2-萘酚和Betti碱，反应在无溶剂条件下进行，使用铝酸盐磺酸纳米颗粒（ASA NPs）作为可回收催化剂。ASA NPs通过净氯磺酸与高纯度铝酸钠的简单反应制备。 ASA NPs通过傅里叶变换红外光谱、X射线粉末衍射、透射电子显微镜、能量色散X射线、热重分析和UV扩散/反射技术进行了表征。根据热重分析和使用Coats-Redfern模型评估的分解热步骤的一些活化参数，催化剂显示出高热稳定性。该方法的优点包括高产率、短反应时间、容易的后处理、成本低廉以及催化剂的可重用性。

  DOI：

  10.1016/j.crci.2016.02.003

文献信息

• Preparation and characterization of Fe3O4@SiO2@PMA:AS an efficient and recyclable nanocatalyst for the synthesis of 1-amidoalkyl-2-naphthols
  作者：Mohsen Esmaeilpour、Jaber Javidi、Maryam Zandi

  DOI：10.1016/j.materresbull.2014.04.019

  日期：2014.7

  superparamagnetic Fe 3 O 4 @SiO 2 that is synthesized based on several stages. First of all, the Fe 3 O 4 @SiO 2 nanosphere core-shell is synthesized. Then, H 3 PMo 12 O 40 nanoparticles were synthesized by the treatment of H 3 PMo 12 O 40 with n -Octane as solvent by a solvothermal method and this nano hetero polyacid immobilized onto the imidazole functionalized Fe 3 O 4 @SiO 2 nanoparticles. The

  摘要 在本文中，我们报道了一种基于多个阶段合成的功能化超顺磁性 Fe 3 O 4 @SiO 2 的制备方法。首先，合成了Fe 3 O 4 @SiO 2 纳米球核壳。然后，通过溶剂热法用正辛烷作为溶剂处理H 3 PMo 12 O 40 合成H 3 PMo 12 O 40 纳米颗粒，并将该纳米杂多酸固定在咪唑官能化的Fe 3 O 4 @SiO 2 纳米颗粒上。样品的结构通过XRD、TEM、DLS、FE-SEM、FT-IR、N 2 吸附-解吸等温线分析和VSM表征。此外，还描述了一种使用 β-萘酚、醛和乙酰胺的多组分、一锅缩合反应制备酰胺烷基萘酚的有效和直接的方案，在无溶剂和微波条件下，在 Fe 3 O 4 @SiO 2 -imid-PMA n 存在下苯甲酰胺和尿素。此外，纳米催化剂可以很容易地通过磁场回收并在接下来的反应中重复使用至少 5 次，而不会明显降低催化活性。
• Efficient One-Pot Syntheses of Betti Bases Catalyzed by 1-Methyl-3-(2-(sulfooxy)ethyl)-1<i>H</i>-imidazol-3-ium Chloride
  作者：C. Wang、Y. Wan、H.-Y. Wang、L.-L. Zhao、J.-J. Shi、X.-X. Zhang、H. Wu

  DOI：10.1002/jhet.1124

  日期：2013.5

  The efficient one‐pot syntheses of Betti bases by the three‐component reaction of aromatic aldehyde, 2‐naphthalen, and acetonitrile (or benzamide) catalyzed by 1‐methyl‐3‐(2‐(sulfooxy)ethyl)‐1H‐imidazol‐3‐ium chloride is reported. The solvent can be recycled easily.

  通过1-甲基-3-（2-（磺氧基）乙基）-1H-咪唑催化的芳香醛，2-萘和乙腈（或苯甲酰胺）的三组分反应有效地一锅合成Betti碱报道了氯化三 该溶剂可以容易地回收。
• Eco-friendly and efficient multi-component method for preparation of 1-amidoalkyl-2-naphthols under solvent-free conditions by dodecylphosphonic acid (DPA)
  作者：Maryam Zandi、Ali Reza Sardarian

  DOI：10.1016/j.crci.2011.11.012

  日期：2012.4

  Résumé An efficient and direct eco-friendly protocol for the preparation of 1-amidoalkyl-2-naphthols employing a multi-component, one-pot condensation reaction between β-naphthol, aromatic or aliphatic aldehydes and benzamide or acetamide in the presence of dodecylphosphonic acid under solvent-free conditions has been described.

  个人简历 使用多组分一锅煮缩合反应，在无溶剂条件下，以十二烷基膦酸作为催化剂，实现β-萘酚、芳香或脂肪醛和苯甲酰胺或乙酰胺制备1-酰胺基烷基-2-萘酚的高效、直接环保合成方法。
• Discovery of an in situ carbocationic system using trityl chloride as a homogeneous organocatalyst for the solvent-free condensation of β-naphthol with aldehydes and amides/thioamides/alkyl carbamates in neutral media
  作者：Ardeshir Khazaei、Mohammad Ali Zolfigol、Ahmad Reza Moosavi-Zare、Fereshteh Abi、Abdolkarim Zare、Hamideh Kaveh、Vahid Khakyzadeh、Masoud Kazem-Rostami、Abolfath Parhami、Hossein Torabi-Monfared

  DOI：10.1016/j.tet.2012.10.042

  日期：2013.1

  Trityl chloride (TrCl), efficiently catalyzes the one-pot multi-component condensation of β-naphthol with aromatic aldehydes and amides/thioamides/carbamates such as acetamide, benzamide, nicotinamide, thioacetamide, and methylcarbamate under solvent-free and neutral conditions to afford 1-amido-alkyl-2-naphthols, 1-thioamido-alkyl-2-naphthols, and 1-carbamato-alkyl-2-naphthols in high yields and very

  三苯甲基氯（TrCl）在无溶剂和中性条件下有效催化β-萘酚与芳族醛和酰胺/硫代酰胺/氨基甲酸酯（如乙酰胺，苯甲酰胺，烟酰胺，硫代乙酰胺和氨基甲酸甲酯）的一锅多组分缩合反应，从而制得1-酰胺基烷基-2-萘酚，1-硫基氨基烷基-2-萘酚和1-氨基甲酰基烷基-2-萘酚的收率很高，反应时间很短。从机理上讲，有趣的是，通过原位生成具有固有不稳定性的三苯甲基碳阳离子的三苯甲基氯在中性介质中作为可重复使用的均相有机催化剂是有效的。
• Saccharin Sulfonic Acid (SASA) as a Highly Efficient Catalyst for the Condensation of 2-Naphthol With Arylaldehydes and Amides (Thioamides or Alkyl Carbamates) Under Green, Mild, and Solvent-Free Conditions
  作者：Abdolkarim Zare、Hamideh Kaveh、Maria Merajoddin、Ahmad Reza Moosavi-Zare、Alireza Hasaninejad、Mohammad Ali Zolfigol

  DOI：10.1080/10426507.2012.692131

  日期：2013.5.1

  Abstract Saccharin sulfonic acid (SaSA) is used as a highly efficient and recyclable catalyst for the one-pot multicomponent condensation of 2-naphthol with arylaldehydes and amides (thioamides or alkyl carbamates) under green, mild (70 °C), and solvent-free conditions. In this reaction, 1-amidoalkyl-2-naphthols, 1-thioamidoalkyl-2-naphthols, 1-carbamatoalkyl-2-naphthols, bis(1-amidoalkyl-2-naphthol)s

  摘要 糖精磺酸 (SaSA) 是一种高效、可回收的催化剂，用于 2-萘酚与芳醛和酰胺（硫代酰胺或氨基甲酸烷基酯）在绿色、温和 (70 °C) 和溶剂下的一锅多组分缩合反应。免费条件。在该反应中，1-酰氨基烷基-2-萘酚、1-硫代酰氨基烷基-2-萘酚、1-氨基甲酰烷基-2-萘酚、双(1-酰氨基烷基-2-萘酚)和双(1-氨基甲酰烷基-2-萘酚) )s 以高到极好的收率和相对较短的反应时间生产。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要