4-(4-bromophenyl)-2-phenyl-4H,5H-pyrano[3,2-c]chromen-5-one

• 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-bromophenyl)-2-phenyl-4H,5H-pyrano[3,2-c]chromen-5-one
• 英文别名: 4-(4-bromophenyl)-2-phenylpyrano[3,2-c]chromen-5(4H)-one；4-(4-bromophenyl)-2-phenyl-4H-pyrano[3,2-c]chromen-5-one
• 化学式: C₂₄H₁₅BrO₃
• 分子量: 431.285
• InChiKey: HUTYHJGRIWAGFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-溴查尔酮 在 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 3.5h， 生成 4-(4-bromophenyl)-2-phenyl-4H,5H-pyrano[3,2-c]chromen-5-one
  参考文献：
  名称：

  Jacquot; Refouvelet, Bernard; Bermont, Pharmazie, 2002, vol. 57, # 4, p. 233 - 237

  摘要：

  DOI：

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。
• Brønsted acidic ionic liquid-catalyzed tandem reaction: an efficient approach towards regioselective synthesis of pyrano[3,2-c]coumarins under solvent-free conditions bearing lower E-factors
  作者：Sachinta Mahato、Sougata Santra、Rana Chatterjee、Grigory V. Zyryanov、Alakananda Hajra、Adinath Majee

  DOI：10.1039/c7gc01158j

  日期：——

  and represents a green synthetic protocol. The catalytic reaction proceeded very smoothly under solvent-free conditions and showed high regioselectivity. Clean reaction, non-chromatographic purification technique, easily accessible reactants, metal and solvent-free and environmentally friendly reaction conditions are the notable advantages of this procedure. In addition, this method possesses lower E-Factors

  发现1-丁烷磺酸-3-甲基咪唑鎓甲苯磺酸盐，[BSMIM] OTs是在无溶剂条件下将4-羟基香豆素与查耳酮串联环化以合成吡喃并[3,2-c]香豆素的出色催化剂。 。所开发的方案适用于从具有各种取代基的易于接近的查耳酮构建生物学上重要的吡喃香豆素。该反应可能通过迈克尔加成反应然后环化进行。还证明了催化剂再循环的可行性。该方法仅产生水作为副产物，代表绿色的合成方案。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。干净的反应，非色谱纯化技术，容易获得的反应物，无金属，无溶剂和环境友好的反应条件是该程序的显着优势。另外，该方法具有较低的电子因子。
• 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
• Molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins with secondary benzyl alcohols
  作者：Xufeng Lin、Xixiang Dai、Zhenjun Mao、Yanguang Wang

  DOI：10.1016/j.tet.2009.09.007

  日期：2009.11

  A highly efficient method for the C-C bond formation via molecular iodine-catalyzed C3-alkylation reaction of 4-hydroxycoumarins with benzylic, benzhydrylic, allylic, and propargyl alcohols at 50 degrees C in MeNO2 is described. The 3-alkylated-4-hydroxycoumarins were obtained in good yields (up to 97%). By applying this reaction as the key step, a multi-substituted pyranocoumarin can easily be synthesized in a one-pot procedure. The advantages of this method are broad scope, mild conditions, and easy handling since water is the only side product. (C) 2009 Elsevier Ltd. All rights reserved.