N-[(2-Hydroxynaphthalen-1-yl)(3,4,5-trimethoxyphenyl)methyl]acetamide | 1071443-85-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-[(2-Hydroxynaphthalen-1-yl)(3,4,5-trimethoxyphenyl)methyl]acetamide
• 英文别名: N-[(2-hydroxynaphthalen-1-yl)-(3,4,5-trimethoxyphenyl)methyl]acetamide
• CAS: 1071443-85-0
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: BDAGSJAYDWTTAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  77
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  乙酰胺 、 3,4,5-三甲氧基苯甲醛 、 2-萘酚 在 Al(H₂PO₄)3 作用下， 反应 4.0h， 以63%的产率得到N-[(2-Hydroxynaphthalen-1-yl)(3,4,5-trimethoxyphenyl)methyl]acetamide
  参考文献：
  名称：

  酰胺烷基萘酚的环保制备

  摘要：

  摘要 一种新的、简便且具有成本效益的方法，包括在 Al(H2PO4)3 存在下使用 β-萘酚、芳香醛和酰胺的三组分一锅缩合反应无溶剂合成酰氨基烷基萘酚作为在热条件和微波辐射下的多相催化剂已被描述。这种新方法具有始终如一的出色收率和较短的反应时间的优点。该催化剂在反应条件下表现出非常稳定的催化活性，并且可以回收再利用。

  DOI：

  10.1080/00397910802006396

文献信息

• Sulfonated polynaphthalene as an effective and reusable catalyst for the one-pot preparation of amidoalkyl naphthols: DFT and spectroscopic studies
  作者：Seied Ali Pourmousavi、Parvin Moghimi、Fatemeh Ghorbani、Mehdi Zamani

  DOI：10.1016/j.molstruc.2017.05.010

  日期：2017.9

  (ESP) map and spectroscopic analysis of some selected amidoalkyl naphthols. The thermochemical parameters of reactions including enthalpy, internal energy, entropy and Gibbs free energy were also investigated. The theoretically calculated infrared (IR) and 1 H nuclear magnetic resonance (NMR) spectra of title compounds were compared to the experimental data. Based on the results, the synthesis of amidoalkyl

  摘要 磺化聚萘 (S-PNP) 作为一种碳基固体酸，可有效催化酰胺烷基萘酚的一锅三组分合成。描述了在无热溶剂条件下，在 S-PNP 存在下，取代芳基醛、2-萘酚和酰胺（苯甲酰胺和乙酰胺）或尿素的三组分过程。反应时间短、产量高和易于处理是该协议的优点。此外，催化剂可以很容易地回收和再利用，而不会明显地显着损失活性。此外，借助 M06-2X 和 B3LYP 方法，密度泛函理论 (DFT) 用于研究一些选定的酰氨基烷基萘酚的优化结构、分子轨道、静电势 (ESP) 图和光谱分析。反应的热化学参数包括焓，还研究了内能、熵和吉布斯自由能。将标题化合物的理论计算的红外 (IR) 和 1 H 核磁共振 (NMR) 光谱与实验数据进行比较。根据结果​​，酰氨基烷基萘酚的合成是放热的。发现计算的和观察到的光谱数据之间具有良好的一致性。
• Solvent-free synthesis of 1-amidoalkyl-2-naphthols using magnetic nanoparticle-supported 2-(((4-(1-iminoethyl)phenyl)imino)methyl)phenol Cu (II) or Zn (II) Schiff base complexes
  作者：Fatemeh Ghorbani、Hamzeh Kiyani、Seied Ali Pourmousavi、Davood Ajloo

  DOI：10.1007/s11164-020-04142-7

  日期：2020.6

  (((4-(1-iminoethyl)phenyl)imino)methyl)phenols were successfully synthesized, characterized, and applied in the one-pot three-component reaction of substituted benzaldehydes, 2-naphthol, and amides for synthesis of 1-amidoalkyl-2-naphthols. These three-component processes occurred under solvent-free reaction conditions at 80 °C. The magnetically recoverable supported Schiff base metal catalysts can

  成功地合成，表征了两种磁性纳米粒子负载的2-（（（（4-（1-亚氨基乙基）苯基）亚氨基）甲基）苯酚，并将其应用于取代的苯甲醛，2-萘酚和用于合成1-酰胺基烷基-2-萘甲酰胺的酰胺。这些三组分过程发生在80°C的无溶剂反应条件下。磁性可回收的负载席夫碱金属催化剂可在模型反应中重复使用几次。通过施加外部磁体，也容易将合成的催化剂与反应混合物分离。该程序的优点是操作简单，无需使用危险的有机溶剂。
• Zirconocene dichloride catalyzed multi-component synthesis of 1-amidoalkyl-2-naphthols at ambient temperature
  作者：Sharanabasappa Khanapure、Megha Jagadale、Rajashri Salunkhe、Gajanan Rashinkar

  DOI：10.1007/s11164-015-2136-9

  日期：2016.3

  Zirconocene dichloride (Cp2ZrCl2) was found to be highly efficient catalyst for the synthesis of structurally diverse 1-amidoalkyl-2-naphthols by one-pot multi-component reaction (MCR) of 2-naphthol with a variety of aryl aldehydes and amides under ambient temperature. The activation of both carbonyl groups of aryl aldehydes and the o-quinine methide intermediate accounts for the high reactivity of Cp2ZrCl2.

  研究发现，二氯化锆（Cp2ZrCl2）是一种高效催化剂，可在常温下通过 2-萘酚与多种芳基醛和酰胺的单锅多组分反应（MCR）合成结构多样的 1-氨基烷基-2-萘酚。由于 Cp2ZrCl2 具有很高的反应活性，芳基醛的羰基和邻喹甲酰胺中间体都被活化。
• PPA-SiO₂–Catalyzed Multicomponent Synthesis of Amidoalkyl Naphthols
  作者：Hamid Reza Shaterian、Asghar Hosseinian、Majid Ghashang

  DOI：10.1080/00397910802138231

  日期：2008.9.12

  Silica gel-supported polyphosphoric acid (PPA-SiO2) was found to be an efficient catalyst for the multicomponent condensation reaction of aryl aldehydes, 2-naphthol, and urea or amides to afford the corresponding 1-amidoalkyl-2-naphthols in good to excellent yields. This new approach consistently had short reaction times, high conversions, clean reaction profiles, and simple experimental and workup procedures.
• Silica gel supported –SO3H functionalised benzimidazolium based ionic liquid as a mild and effective catalyst for rapid synthesis of 1-amidoalkyl naphthols
  作者：Deepali A. Kotadia、Saurabh S. Soni

  DOI：10.1016/j.molcata.2011.11.003

  日期：2012.2

  The use of ionic liquid in catalysis is attracting more and more attention in the field of chemistry. In line with the research we have studied Supported Ionic Liquid Catalyst (SILC) which consist of benzimidazolium based ionic liquid immobilized on silica based solid support. The SILC proved to be an efficient heterogeneous catalyst for solvent less synthesis of 1-amidoalkyl naphthols from 2-naphthol, amides and aldehydes. The process represents a simple, ecologically safer, cost effective route to 1-amidoalkyl naphthol with high product quality, as well as easy product recovery and catalyst recycling. (C) 2011 Elsevier B.V. All rights reserved.