N-[(2-hydroxynaphthalen-1-yl)-o-tolylmethyl]-acetamide

• 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)-o-tolylmethyl]-acetamide
• 英文别名: N-[(2-hydroxynaphthalen-1-yl)-(2-methylphenyl)methyl]acetamide
• 化学式: C₂₀H₁₉NO₂
• 分子量: 305.376
• InChiKey: MXMPLYDGACZZNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙酰胺 、 2-甲基苯甲醛 、 2-萘酚 在 1,3-disulfonic acid imidazolium chloride 作用下， 反应 0.05h， 以90%的产率得到N-[(2-hydroxynaphthalen-1-yl)-o-tolylmethyl]-acetamide
  参考文献：
  名称：

  磺酸官能化的咪唑鎓盐快速合成1-氨基烷基-2-萘酚

  摘要：

  新型磺酸官能化的咪唑鎓盐，包括3-甲基-1-磺酸咪唑鎓氯化物{[Msim] Cl}（离子液体），1,3-二磺酸咪唑鎓氯化物{[Dsim] Cl}（离子液体）和3 -甲基-1-磺酸咪唑四氯铝酸盐{[Msim] AlCl 4 }（固体）在无溶剂条件下有效催化β-萘酚与芳族醛和酰胺衍生物的一锅多组分缩合，得到1-酰胺基烷基- 2-萘酚具有优异的收率（81–96％）和非常短的反应时间（1–40分钟）。

  DOI：

  10.1016/j.apcata.2011.04.013

文献信息

• A modified reaction for the preparation of amidoalkyl naphthols
  作者：Hamid Reza Shaterian、Hossein Yarahmadi

  DOI：10.1016/j.tetlet.2007.12.093

  日期：2008.2

  An efficient synthesis of amidoalkyl naphthols using FeCl3·SiO2 as a heterogeneous catalyst is described. This thermal solvent-free procedure offers advantages such as shorter reaction times, simple work-up, excellent yields, and recovery and reusability of the catalyst.

  描述了使用FeCl 3 ·SiO 2作为非均相催化剂的酰胺基烷基萘的高效合成方法。这种无溶剂热溶剂的方法具有以下优点，例如反应时间短，后处理简单，产率高以及催化剂的回收率和可重复使用性。
• An efficient, simple and expedition synthesis of 1-amidoalkyl-2-naphthols as ‘drug like’ molecules for biological screening
  作者：Hamid Reza Shaterian、Hossein Yarahmadi、Majid Ghashang

  DOI：10.1016/j.bmcl.2007.11.035

  日期：2008.1

  An efficient and direct protocol for the preparation of amidoalkyl naphthols employing a multi-component, one-pot condensation reaction of beta-naphthol, aromatic aldehydes and acetamide in the presence of ferric hydrogensulfate under solvent, solvent-free and microwave conditions is described. The thermal solvent-free and microwave green procedures offer advantages such as shorter reaction times,

  描述了在溶剂，无溶剂和微波条件下，在硫酸氢铁存在下，使用β-萘酚，芳族醛和乙酰胺的多组分一锅缩合反应制备酰胺烷基萘的有效直接方法。无溶剂的热法和微波绿色法具有诸如缩短反应时间，简化后处理，优异的收率，催化剂的回收率和可重复使用性等优点。值得注意的是，可以通过酰胺水解将1-酰胺基甲基-2-萘酚转化为重要的生物学“药物样”活性1-氨基甲基-2-萘酚衍生物。
• Three-Component reaction between 2-naphthol, Aromatic Aldehydes and Acetonitrile in the Presence of Chlorosulfonic Acid Yields 1-(Acetylamino (Aryl)Methyl)-2-Naphthols
  作者：Mohammad Anary-Abbasinejad、Alireza Hassanabadi、Maryam Kamali-Gharamaleki、Azimeh Saidipoor、Hossein Anaraki-Ardakani

  DOI：10.3184/030823407x266207

  日期：2007.11

  The one-pot, three-component reaction between aryl aldehydes, 2-naphthol, and acetonitrile in the presence of chlorosulfonic acid affords 1-[acetylamino(aryl)methyl]-2-naphthols in excellent yields.

  在氯磺酸存在下，芳基醛、2-萘酚和乙腈发生单锅三组分反应，生成 1-[乙酰氨基（芳基）甲基]-2-萘酚，收率极高。
• Nanocrystalline TiO2–HClO4 catalyzed three-component preparation of derivatives of 1-amidoalkyl-2-naphthol, 1-carbamato-alkyl-2-naphthol, 1-(α-aminoalkyl)-2-naphthol, and 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one
  作者：Hamid Reza Shaterian、Majid Mohammadnia

  DOI：10.1007/s11164-012-0938-6

  日期：2013.11

  1-Amidoalkyl-2-naphthols, 1-carbamatoalkyl-2-naphthols, and 1-(α-aminoalkyl)-2-naphthols have been prepared by three-component reaction of 2-naphthol, aromatic aldehydes, and NH compounds, i.e. amides, carbamates, and secondary amines, respectively, in the presence of a catalytic amount of nanocrystalline TiO2–HClO4. In addition, 12-aryl-8,9,10,12-tetrahydrobenzo[a]-xanthen-11-one derivatives have been synthesized by reaction of 2-naphthol, aromatic aldehydes, and dimedone in the presence of the same nano catalyst. These reactions were studied under solvent-free conditions. This white acidic heterogeneous catalyst is very stable under the reaction conditions and was reused several times without significant loss of activity.

  在催化剂纳米晶 TiO2-HClO4 的存在下，通过 2-萘酚、芳香醛和 NH 化合物（即酰胺、氨基甲酸酯和仲胺）的三组分反应，分别制备了 1-氨基烷基-2-萘酚、1-氨基甲酰基-2-萘酚和 1-(α-氨基烷基)-2-萘酚。此外，在相同的纳米催化剂存在下，通过 2-萘酚、芳香醛和二甲酮的反应，合成了 12-芳基-8,9,10,12-四氢苯并[a]-氧杂蒽-11-酮衍生物。这些反应是在无溶剂条件下进行研究的。这种白色酸性异相催化剂在反应条件下非常稳定，可重复使用多次，且活性无明显下降。
• Synthesis, characterization, and catalytic application of PbS nanoparticles for the synthesis of amidoalkyl naphthols under solvent-free conditions
  作者：Ashok V. Borhade、Bhagwat K. Uphade、Dipak R. Tope

  DOI：10.1007/s11164-012-0956-4

  日期：2014.1

  A simple one-pot synthesis has been developed for the synthesis of amidoalkyl naphthols using an efficient and recyclable nanocrystalline PbS catalyst under solvent-free condition. Using this nanocrystalline solid catalyst, the reactions could be carried out under mild reaction conditions with very good yield (85–95 %). This catalyst could be recycled very easily, which makes this methodology environmentally benign. The biologically active drug-like molecule 1-aminomethyl-2-naphthol derivatives can be easily obtained from 1-amidomethyl-2-naphthol by amide hydrolysis reaction in the presence of PbS nanoparticles. Characterization of the catalyst was performed by X-ray diffraction, transmission electron microscopy, and adsorption/desorption analysis (BET).

  利用一种高效且可回收的纳米晶 PbS 催化剂，在无溶剂条件下开发了一种简单的一锅合成法，用于合成氨基烷基萘酚。使用这种纳米晶体固体催化剂，反应可以在温和的反应条件下进行，并且产率非常高（85-95%）。这种催化剂非常容易回收，因此这种方法对环境无害。在 PbS 纳米颗粒存在的情况下，通过酰胺水解反应，可以很容易地从 1-amidomethyl-2-naphthol 中获得具有生物活性的类药分子 1-amidomethyl-2-naphthol 衍生物。通过 X 射线衍射、透射电子显微镜和吸附/解吸分析（BET）对催化剂进行了表征。