2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one | 1621-67-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
• 英文别名: 3'-Hydroxy-4'-methoxy-flavon；7,3-Dihydroxy-4'-methoxyflavone；2-(3-hydroxy-4-methoxyphenyl)chromen-4-one
• CAS: 1621-67-6
• 化学式: C₁₆H₁₂O₄
• 分子量: 268.269
• InChiKey: NNOMLEVVDUSRPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-烯丙氧基-4-甲氧基苯甲醛 在 碘 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 24.5h， 生成 2-(3-hydroxy-4-methoxyphenyl)-4H-chromen-4-one
  参考文献：
  名称：

  烯丙基保护法轻松合成羟化黄酮的新方法

  摘要：

  碘诱导的2'-羟基查尔酮的氧化环化为各种羟基黄酮和类似物提供了一种简单，高效的方法。该过程在温和的条件下进行，可耐受各种官能团，并以良好至极好的收率提供羟基黄酮。烯丙基保护的苯乙酮和苯甲醛在相似条件下被平滑脱醛。

  DOI：

  10.1002/jhet.1580

文献信息

• Dual-Metal Single Atoms with Dual Coordination for the Domino Synthesis of Natural Flavones
  作者：Xin Zhao、Ruiqi Fang、Fengliang Wang、Xiangpeng Kong、Yingwei Li

  DOI：10.1021/jacsau.2c00582

  日期：2023.1.23

  The regulation of coordination configurations of single-atom sites is highly desirable to boost the catalytic performances of SA catalysts. Here, we demonstrate a versatile complexation-deposition strategy for the synthesis of 13 kinds of dual-metal SA site pairs with uniform and exclusive coordination configurations. The preparation is specifically exemplified by the fabrication of Cu and Co single-atom

  非常需要调节单原子位点的配位构型以提高SA催化剂的催化性能。在这里，我们展示了一种通用的络合沉积策略，用于合成 13 种具有统一和排他配位配置的双金属 SA 位点对。通过蚀刻和热解预合成的金属-有机框架模板，制备 Cu 和 Co 单原子对以及 N 和 P 杂原子共存，具体说明了该制备方法。系统表征揭示了 CuN 4 / CoN 3 P 1和 CuN 4 / CoN 2 P 2中 Cu 和 Co SA 位点的均匀且排他性配位构型，电子在其上不对称分布。令人印象深刻的是，与 CuN 4 / CoN 3 P 1和 CuN 4 / CoN 4对应物相比，CuN 4 / CoN 2 P 2位点对在多种天然类黄酮的合成中表现出显着增强的催化活性和选择性。理论计算结果表明，CuN 4 / CoN 2 P 2上的不对称电子分布位点可以通过降低关键中间体生成的能垒来促进氧分子的吸附和解离，从而在动力学上加速氧化偶联反应过程。
• Iodine-PEG as a unique combination for the metal-free synthesis of flavonoids through iodonium-triiodide ion-pair complexation
  作者：Naveen Kumar、Navneet Sharma、Vijay Kumar、Vinay Kumar、Kailash Jangid、Bharti Devi、Ashish Ranjan Dwivedi、Kousik Giri、Rakesh Kumar、Vinod Kumar

  DOI：10.1039/d3ra08810c

  日期：2024.2.14

  the iodonium-triiodide ion couple formed through iodine and PEG-400 complexation. The triiodide anion not only helps in the abstraction of a proton from the acetophenone but also promotes the cyclization of intermediate chalcone to the corresponding flavones. The flavones were obtained in very high yields without using any toxic metal catalysts or harsh reaction conditions. The reaction mechanism was

  开发了一种高效的无金属单步方案，用于从 2-羟基苯乙酮和取代苯甲醛直接合成黄酮。这种化学转化仅由碘和 PEG-400 络合形成的碘鎓-三碘化物离子对促进。三碘化物阴离子不仅有助于从苯乙酮中夺取质子，而且促进中间体查耳酮环化为相应的黄酮。在不使用任何有毒金属催化剂或苛刻的反应条件的情况下，以非常高的产率获得了黄酮。通过一系列测试反应和反应中间体的包埋建立了反应机理。开发的方案可以在较温和的反应条件下以高产率直接获取黄酮，并具有良好的底物兼容性，包括羟基化衍生物。
• Design, synthesis and biological activity of flavonoid derivatives as selective agonists for neuromedin U 2 receptor
  作者：Ming-Liang Ma、Ming Li、Jiao-Jiao Gou、Tian-Yu Ruan、Hai-Shan Jin、Ling-Hong Zhang、Liang-Chun Wu、Xiao-Yan Li、Ying-He Hu、Ke Wen、Zheng Zhao

  DOI：10.1016/j.bmc.2014.08.038

  日期：2014.11

  Central neuromedin U 2 receptor (NMU2R) plays important roles in the regulation of food intake and body weight. Identification of NMU2R agonists may lead to the development of pharmaceutical agents to treat obesity. Based on the structure of rutin, a typical flavonoid and one of the NMU2R agonists we previously identified from an in-house made natural product library, 30 flavonoid derivatives have been synthesized and screened on a cell-based reporter gene assay. A number of compounds were found to be selective and highly potent to NMU2R. For example, the EC50 value of compound NRA 4 is very close to that of NMU, the endogenous peptide ligand of NMU2R. Structure-activity relationship analysis revealed that a 3-hydroxyl group in ring C and a 2'-fluoride group in ring B were essential for this class of compounds to be active against NMU2R. (C) 2014 Elsevier Ltd. All rights reserved.
• Anti-tyrosinase flavone derivatives and their anti-melanogenic activities: Importance of the β-phenyl-α,β-unsaturated carbonyl scaffold
  作者：Jieun Lee、Yeongmu Jeong、Hee Jin Jung、Sultan Ullah、Jeongin Ko、Ga Young Kim、Dahye Yoon、Sojeong Hong、Dongwan Kang、Yujin Park、Pusoon Chun、Hae Young Chung、Hyung Ryong Moon

  DOI：10.1016/j.bioorg.2023.106504

  日期：2023.3
• ENZYME ACTIVITY INDICATORS
  申请人：Burton, Michael

  公开号：EP1438423B1

  公开（公告）日：2007-12-12