N-((2,4-dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)acrylamide | 1010729-02-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-((2,4-dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)acrylamide
• CAS: 1010729-02-8
• 化学式: C₂₀H₁₅Cl₂NO₂
• 分子量: 372.251
• InChiKey: HJNSLVMOYJVPAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.24
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2,4-二氯苯甲醛 、 丙烯酰胺 、 2-萘酚 在 β-cyclodextrin-butane sulfonic acid 作用下， 以 neat (no solvent) 为溶剂， 反应 0.17h， 以90%的产率得到N-((2,4-dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl)acrylamide
  参考文献：
  名称：

  β-环糊精-丁磺酸：无溶剂条件下1-氨基烷基-2-萘多组分合成的有效且可重复使用的催化剂

  摘要：

  据报道，小α-环糊精-丁磺酸是在溶剂-溶剂下通过芳香醛，小-萘酚和酰胺的多组分缩合一锅合成1-氨基烷基-2-萘的有效催化剂。免费条件。这...

  DOI：

  10.1039/c5gc00384a

文献信息

• An Improved Synthesis of Amidoalkyl Phenols Involving a Ritter-Type Reaction
  作者：Biswanath Das、Keetha Laxminarayana、P. Thirupathi、B. Ramarao

  DOI：10.1055/s-2007-990923

  日期：——

  Three-component condensation of phenols, aromatic aldehydes and alkyl nitriles in the presence of a catalytic amount of triflic acid yielded the corresponding amidoalkyl phenols involving a Ritter-type reaction. The products were formed in high yields and in short reaction times.

  在催化量的三氟甲磺酸存在下，苯酚、芳香醛和烷基腈的三组分缩合产生相应的酰胺烷基苯酚，涉及 Ritter 型反应。产物以高产率和短反应时间形成。
• Synthesis, crystal structure, biological evaluation, docking study, and DFT calculations of 1-amidoalkyl-2-naphthol derivative
  作者：Khawla Boudebbous、Houssem Boulebd、Raouf Boulcina、Lamia Bendjeddou、Chawki Bensouici、Hocine Merazig、Abdelmadjid Debache

  DOI：10.1016/j.molstruc.2020.128179

  日期：2020.7

  An eco-friendly and efficient synthesis of N-((2,4-dichlorophenyl)(2-hydroxynaphthalen-1-yl)methyl) acrylamide (NDHA), using phenylboronic acid as catalyst, has been reported. NDHA was fully characterized by various physical and spectroscopic techniques, and the proposed structure was confirmed by single-crystal X-ray analysis. In vitro antioxidant activity has been carried out using DPPH, ABTS, Ferricphenanthroline and CUPRAC assays, and it was found that NDHA is a potent antioxidant agent. This result has been confirmed by DFT calculations. The inhibitory potential of the synthesized compound on cholinesterase and alpha-glucosidase enzymes was also investigated. The results showed that NDHA is a promising AChE and alpha-glucosidase inhibitor. Binding modes between the (R) and (S) enantiomers of NDHA and the target enzymes were determined using docking studies. (C) 2020 Elsevier B.V. All rights reserved.