ethyl-1-(4-methoxyphenyl)-3-methyl-1H-benzo[f]chromene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 英文名称: ethyl-1-(4-methoxyphenyl)-3-methyl-1H-benzo[f]chromene-2-carboxylate
• 英文别名: ethyl 1-(4-methoxyphenyl)-3-methyl-1H-benzo[f]chromene-2-carboxylate
• 化学式: C₂₄H₂₂O₄
• 分子量: 374.436
• InChiKey: SSBINDAKCMNXCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酰乙酸乙酯 、 4-甲氧基苯甲醛 、 2-萘酚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以57%的产率得到ethyl-1-(4-methoxyphenyl)-3-methyl-1H-benzo[f]chromene-2-carboxylate
  参考文献：
  名称：

  A Three-component Reaction of Phenol, Aldehyde, and Active Methylene Substrate under Lewis acid Catalysis: Successful Trapping ofo-Quinone Methide to Afford Benzopyran Systems

  摘要：

  在 BF3.Et2O 催化下，描述了一种涉及活性酚、醛和活性亚甲基底物的三组分缩合反应，以令人满意的收率获得苯并吡喃基产品。

  DOI：

  10.1246/cl.2004.1058

文献信息

• A Three-component Reaction of Phenol, Aldehyde, and Active Methylene Substrate under Lewis acid Catalysis: Successful Trapping of<i>o</i>-Quinone Methide to Afford Benzopyran Systems
  作者：Sabir H. Mashraqui、Mamta B. Patil、Hitesh D. Mistry、Shailesh Ghadigaonkar、Auke Meetsma

  DOI：10.1246/cl.2004.1058

  日期：2004.8

  A three-component condensation involving reactive phenols, aldehydes, and active methylene substrates is described under BF3.Et2O catalysis to afford benzopyranyl products in satisfactory yields.

  在 BF3.Et2O 催化下，描述了一种涉及活性酚、醛和活性亚甲基底物的三组分缩合反应，以令人满意的收率获得苯并吡喃基产品。
• Microwave assisted synthesis of naphthopyrans catalysed by silica supported fluoroboric acid as a new class of non purine xanthine oxidase inhibitors
  作者：Sahil Sharma、Kirti Sharma、Ritu Ojha、Dinesh Kumar、Gagandip Singh、Kunal Nepali、P.M.S. Bedi

  DOI：10.1016/j.bmcl.2013.12.031

  日期：2014.1

  A series of naphthopyrans was synthesized employing silica supported fluoroboric acid under solvent free conditions in a microwave reactor. The catalytic influence of HBF4-SiO2 was investigated in detail to optimize the reaction conditions. The synthesised compounds were evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Structure-activity relationship analyses have also been presented. Among the synthesised compounds, NP-17, NP-19, NP-20, NP-23, NP-24, NP-25 and NP-26 were the active inhibitors with an IC50 ranging from 4 to 17 mu M. Compound NP-19 with a thiophenyl ring at position 1 emerged as the most potent xanthine oxidase inhibitor (IC50 = 4 mu M) in comparison to allopurinol (IC50 = 11.10 mu M) and febuxostat (IC50 = 0.025 mu M). The basis of significant inhibition of xanthine oxidase by NP-19 was rationalized by its molecular docking at MTE binding site of xanthine oxidase. (C) 2013 Elsevier Ltd. All rights reserved.