5,7,3'-trimethoxyflavanone

• 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: 5,7,3'-trimethoxyflavanone
• 英文别名: 5,7-dimethoxy-2-(3-methoxyphenyl)chroman-4-one；5,7-dimethoxy-2-(3-methoxyphenyl)-2,3-dihydro-4H-benzopyran-4-one；5,7-Dimethoxy-2-(3-methoxyphenyl)-2,3-dihydrochromen-4-one
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: BKISWPHWZHJMNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5,7,3'-trimethoxyflavanone 在 C₉H₈IO₄Pol 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以90%的产率得到5,7,3'-trimethoxyflavone
  参考文献：
  名称：

  Selective and efficient oxidative modifications of flavonoids with 2-iodoxybenzoic acid (IBX)

  摘要：

  2-Iodoxybenzoic acid (IBX), a mild and efficient hypervalent iodine oxidant, has been utilised in different reaction conditions to perform several efficient oxidative modifications of flavonoids. Fine-tuning of the reaction conditions allowed remarkably selective modifications of these compounds. At room temperature, IBX proved to be an excellent reagent for a highly regioselective aromatic hydroxylation of monohydroxylated flavanones and flavones, generating the corresponding catecholic derivatives showing high antioxidant activity. At 90 degrees C, IBX efficiently dehydrogenated a large panel of methoxylated flavanones to their corresponding flavones exhibiting anticancer activity. IBX polystyrene has also been utilised to increase the recovery of highly polar compounds. Following the first oxidation, the reagent was recovered and reused in several runs without loss of efficiency and selectivity. The first example of an application of IBX polystyrene in a dehydrogenation reaction has been described. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.06.014
• 作为产物：
  描述：

  2,4,6-三羟基苯乙酮一水合物 在 盐酸 、 potassium carbonate 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 1.5h， 生成 5,7,3'-trimethoxyflavanone
  参考文献：
  名称：

  新型的一氧化氮（NO）产生抑制剂的开发对慢性炎症具有潜在的治疗作用

  摘要：

  炎症是对刺激的复杂生物学反应。活化的巨噬细胞诱导过度释放促炎性细胞因子，而内源性自由基一氧化氮（NO）等介体在多种炎性疾病的进展中起重要作用。天然和合成查耳酮都具有广泛的生物活性。在这项工作中，基于生物活性卡瓦尔查耳酮，设计，合成了39个查耳酮和3种相关化合物，包括几种新化合物，并评估了它们对RAW 264.7细胞中NO产生的抑制作用。新型化合物（E）-1-（2'-羟基-4'，6'-二甲氧基苯基）-3-（3-甲氧基-4-（3-吗啉代丙氧基）苯基）丙-2-烯-1-酮（53）对10μM（IC的NO产生）表现出更好的抑制活性（84.0％）50  = 6.4μM）的细胞毒性（IC 50  > 80μM）在测试化合物中最低。此外，蛋白质印迹分析表明化合物53是诱导型一氧化氮合酶（iNOS）蛋白的有效下调剂。对接研究表明，化合物53也可以对接iNOS的活性位点。此外，在剂量为10 mg / kg /

  DOI：

  10.1016/j.ejmech.2020.112216

文献信息

• Attrition-Enhanced Deracemization and Absolute Asymmetric Synthesis of Flavanones from Prochiral Precursors
  作者：Waku Shimizu、Naohiro Uemura、Yasushi Yoshida、Takashi Mino、Yoshio Kasashima、Masami Sakamoto

  DOI：10.1021/acs.cgd.0c00955

  日期：2020.9.2

  Seven racemic 5,7-dimethoxyflavanones afforded conglomerate crystals upon recrystallization from a solvent. Three methodologies were investigated to achieve asymmetric transformation based on dynamic crystallization of the chiral conglomerate system. The first was chiral symmetry breaking of racemic flavanones by attrition-enhanced deracemization. Continuous suspension of racemic flavanones in a small

  从溶剂中重结晶后，七个外消旋的5,7-二甲氧基黄酮酮提供了凝聚物晶体。研究了三种方法来实现基于手性团聚体系统动态结晶的不对称转化。第一个是通过减磨增强的去消旋作用使外消旋黄烷酮手性对称性破坏。在碱（1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU））和玻璃珠存在下，外消旋黄烷酮在少量丙醇中的连续悬浮促进了手性对称性的破坏并将黄烷酮转化为晶体具有78％至99％ee的（+）-或（-）-对映体。第二种方法涉及中间体醛醇缩合产物的环化，以产生具有90％ee的旋光性黄烷酮，其中涉及可逆的oxa-Michael加成反应以及减磨作用。
• Synthesis of 2-Benzylidene-3(2<i>H</i>)-benzofuran-3-ones (Aurones) by Oxidation of 2′-Hydroxychalcones with Mercury(II) Acetate
  作者：Haruo Sekizaki

  DOI：10.1246/bcsj.61.1407

  日期：1988.4

  The reaction of 2′-hydroxychalcones with mercury(II) acetate in acetic acid gives predominantly 2-benzylidene-3(2H)-benzofuran-3-ones (aurones) in 28–62% yield accompanied by flavanones in 5–21% yield.

  2'-羟基查尔酮与乙酸汞 (II) 在乙酸中的反应主要产生 2-benzylidene-3(2H)-benzofuran-3-ones (aurones)，产率为 28-62%，黄烷酮产率为 5-21% .
• Synthesis and Investigation of Flavanone Derivatives as Potential New Anti-Inflammatory Agents
  作者：Cynthia Sinyeue、Mariko Matsui、Michael Oelgemöller、Frédérique Bregier、Vincent Chaleix、Vincent Sol、Nicolas Lebouvier

  DOI：10.3390/molecules27061781

  日期：——

  Flavonoids are polyphenols with broad known pharmacological properties. A series of 2,3-dihydroflavanone derivatives were thus synthesized and investigated for their anti-inflammatory activities. The target flavanones were prepared through cyclization of 2′-hydroxychalcone derivatives, the later obtained by Claisen–Schmidt condensation. Since nitric oxide (NO) represents an important inflammatory mediator

  黄酮类化合物是具有广泛已知药理特性的多酚。因此合成了一系列 2,3-二氢黄烷酮衍生物并研究了它们的抗炎活性。目标黄烷酮通过 2'-羟基查耳酮衍生物的环化制备，后者通过 Claisen-Schmidt 缩合获得。由于一氧化氮 (NO) 是一种重要的炎症介质，因此使用 Griess 试验在体外评估了各种黄烷酮对 LPS 诱导的 RAW 264.7 巨噬细胞中 NO 产生的影响。最活跃的化合物是黄烷酮 (4G)、2'-羧基-5,7-二甲氧基黄烷酮 (4F)、4'-溴-5,7-二甲氧基黄烷酮 (4D) 和 2'-羧基黄烷酮 (4J) ，IC50 值分别为 0.603、0.906、1.030 和 1.830 µg/mL。相比之下，松松素的 IC50 值为 203.60 µg/mL。因此，在这项工作中合成的衍生物与松松素相比具有更高的 NO 抑制能力，证明了药物调节对提高天然分子的生物学潜力的重要性。SAR
• One-Pot Synthesis of 1,3,5-Triarylpyrazoles
  作者：Shufang Huang、Huazhou Ying、Yongzhou Hu

  DOI：10.1002/jhet.927

  日期：2013.5

  A series of novel 1,3,5-triarylpyrazoles were synthesized from flavanones, arylhydrazines, and trimethyl phosphate in an one-pot procedure. Facile reaction process, easy after-reaction workshop, and good yields are the distinct characteristics of the developed protocol. The target compounds were characterized by element analysis, infrared ray (IR), 1H NMR spectra, and electrospray ionization-mass spectrometry. The structure of representative compound (C23H20N2O3, Mr = 372.42) was further confirmed by X-ray diffraction. It crystallizes in monoclinic, space group P 21/c, a = 8.9720(5), b = 24.5523(13), c = 8.9687(6) angstrom, = 90.0000, = 102.6417(17), = 90.0000 degrees, V = 1927.76(20) angstrom 3, Z = 4, (MoK) = 0.086, F(000) = 784, Dc = 1.283 g/cm3, the final R = 0.0349 and wR = 0.0844 for 1668 observed reflections (I > 2 sigma(I))
• SEKIZAKI, HARUO, BULL. CHEM. SOC. JAP., 61,(1988) N 4, 1407-1409
  作者：SEKIZAKI, HARUO

  DOI：——

  日期：——