4-(4-methoxyphenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one | 1443992-30-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-(4-methoxyphenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one
• 英文别名: 4-(4-methoxyphenyl)-2-phenyl-4H-pyrano[3,2-c]chromen-5-one
• CAS: 1443992-30-0
• 化学式: C₂₅H₁₈O₄
• 分子量: 382.416
• InChiKey: FJRQIFOGUBOCBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  1-(4-methoxyphenyl)-3-phenylprop-2-yn-1-ol 在 N-甲基吗啉 、 aluminium(III) triflate 、 copper(I) bromide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 9.0h， 生成 4-(4-methoxyphenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one
  参考文献：
  名称：

  Al(OTf)3-Catalyzed Preparation of 4-Hydroxy-3-propargylic ­Coumarins and Subsequent Regioselective Cyclization towards Furo- or Pyrano[3,2-c]coumarins

  摘要：

  An efficient and economical approach to functionalized furo[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives has been developed from 4-hydroxy-3-(prop-2-ynyl)coumarin derivatives through organocatalysis or metallo-organocatalysis. Selective 5-exo-dig' or 6-endo-dig' cyclization of the 4-hydroxy-3-(prop-2-ynyl)coumarin substrates could be achieved under organocatalytic {1,8-diazabicyclo[5.4.0]undec-7-ene} or metallo-organocatalytic (N-methylmorpholine/CuBr) conditions, respectively, to yield potentially bioactive heterocycles in excellent yields.

  DOI：

  10.1055/s-0034-1379971

文献信息

• Soluble Glass, an Efficient Promoter for the Cascade Addition-Cyclization Reaction of 4-Hydroxycoumarins to Chalcone Derivatives
  作者：Mojtaba Lashkari、Majid Ghashang、Ali Abedi-Madiseh

  DOI：10.1080/00304948.2020.1833694

  日期：2021.1.2

  (2021). Soluble Glass, an Efficient Promoter for the Cascade Addition-Cyclization Reaction of 4-Hydroxycoumarins to Chalcone Derivatives. Organic Preparations and Procedures International: Vol. 53, No. 1, pp. 52-58.

  （2021年）。可溶性玻璃，4-羟基香豆素与查尔酮衍生物的级联加成环化反应的有效促进剂。国际有机制剂和程序：第 53，第1号，第52-58页。
• Design, synthesis and evaluation of 2,4-diarylpyrano[3,2-c]chromen-5(4H)-one as a new class of non-purine xanthine oxidase inhibitors
  作者：Harpreet S. Virdi、Sahil Sharma、Samir Mehndiratta、P. M. S. Bedi、Kunal Nepali

  DOI：10.3109/14756366.2014.961446

  日期：2015.9.3

  catalyst among the tested ones. The conjugates were evaluated for in-vitro xanthine oxidase activity. The results of the in-vitro assay were quite promising as some conjugates were endowed with remarkable inhibitory potential against the enzyme. HV-8, 11 and 12 were found to be high-potent inhibitors with HV-11 (the most potent inhibitor) possessing an IC50 value of 2.21 µM. The most active conjugate HV-11

  摘要鉴于分子杂交技术在药物设计中的最新成功，本研究设计并合成了2,4-二芳基吡喃并[3,2-c] chromen-5（4H）-作为香豆素和查耳酮的缀合物。 。研究了各种路易斯酸在纯净条件下合成设计的共轭物的催化效率，并优化了SiO2（200-400目）-ZnCl2作为测试催化剂中的最佳催化剂。评价缀合物的体外黄嘌呤氧化酶活性。体外测定的结果非常有前途，因为某些结合物具有明显的抑制酶的潜力。发现HV-8、11和12是高效抑制剂，而HV-11（最有效的抑制剂）的IC50值为2.21 µM。评价活性最高的缀合物HV-11的抑制类型，发现其为混合型抑制剂。还计算了某些选定的共轭物对Lipinski规则的依从性。
• Microwave-promoted efficient synthesis of pyrano[3,2-c]chromen-5(4H)-ones under catalyst and solvent-free conditions
  作者：Mudumala Veeranarayana Reddy、Badur Siva Kumar、Kwon Taek Lim、Byung Gwon Cho、Yeon Tae Jeong

  DOI：10.1016/j.tetlet.2015.12.061

  日期：2016.1

  An efficient and rapid synthesis of a new class of diversely functionalized pyrano[3,2-c]chromen-5(4H)-ones has been achieved via one-pot three-component reaction of 4-hydroxy-2H-chromen-2-one, aldehydes, and acetophenones under microwave irradiation in catalyst and solvent-free conditions. The present methodology offers several advantages such as short reaction time, simple operational procedure,

  通过4-羟基-2 H-铬原子-的一锅三组分反应，已经高效，快速地合成了新型的多种官能化的吡喃并[3,2 - c ] chromen-5（4 H）-酮。在无催化剂和无溶剂的条件下，微波辐射下的2-one，醛和苯乙酮。本方法提供了许多优点，例如反应时间短，操作步骤简单，避免了有毒溶剂和催化剂，产物的产率高以及对底物多样性的耐受性。
• Regioselective synthesis of pyrano[3,2-c]coumarins via Cu(II)-catalyzed tandem reaction
  作者：Avik Kumar Bagdi、Adinath Majee、Alakananda Hajra

  DOI：10.1016/j.tetlet.2013.05.061

  日期：2013.7

  Efficient synthesis of pyrano[3,2-c]coumarins has been achieved via copper(II) triflate catalyzed tandem reaction of 4-hydroxycoumarin with α,β-unsaturated carbonyl compounds in high yields. The catalytic reaction proceeded very smoothly under solvent-free conditions and showed high regioselectivity. The synthetic potential of this methodology was explored to 4-hydroxy-6-methyl-2-pyrone successfully

  吡喃并[3,2- c ]香豆素的有效合成已通过三氟甲磺酸铜（II）催化4-羟基香豆素与α，β-不饱和羰基化合物的串联反应以高收率实现。在无溶剂条件下，催化反应进行得非常顺利，并具有很高的区域选择性。该方法的合成潜力已成功地探索为4-羟基-6-甲基-2-吡喃酮。
• Efficient Route to Highly Functionalized Chalcone-Based Pyranocoumarins via Iodine-Promoted Michael Addition Followed by Cyclization of 4-Hydroxycoumarins
  作者：Naseem Ahmed、B. Venkata Babu

  DOI：10.1080/00397911.2012.763099

  日期：2013.11.17

  Abstract Molecular iodine is used as an efficient promoter in the regioselective synthesis of highly functionalized chalcone-based pyranocoumarin derivatives using 4-hydroxycoumarin in acetic acid solvent at 100 °C. Under optimized reaction conditions, our protocol (Michael addition followed by intermolecular cyclization) has tolerance for many functional groups and gave products in good to excellent

  摘要 在 100 °C 的乙酸溶剂中使用 4-羟基香豆素对高度官能化的查尔酮基吡喃香豆素衍生物进行区域选择性合成时，分子碘被用作有效的促进剂。在优化的反应条件下，我们的方案（迈克尔加成，然后分子间环化）对许多官能团具有耐受性，并在 1-2 小时内以良好的产率（75-98%）提供产品。[本文提供补充材料。访问出版商的 Synthetic Communications® 在线版，获取以下免费补充资源：完整的实验和光谱细节。] 图形摘要