(Z)-4,6-dimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-4,6-dimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 4,4',6-Trimethoxyaurone；(2Z)-4,6-dimethoxy-2-[(4-methoxyphenyl)methylidene]-1-benzofuran-3-one
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: HOVVZRFSBDVBHE-PXNMLYILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  (Z)-4,6-dimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.0h， 以89%的产率得到4,6-dimethoxy-2-(4-methoxyphenylmethyl)benzofuran-3(2H)-one
  参考文献：
  名称：

  Design, Synthesis and Biological Activities of Dihydroaurones

  摘要：

  为了扩大奥罗宁在无色食品和化妆品应用中的适用性，设计了一系列二氢奥罗宁，以模拟天然奥罗宁和合成奥罗宁。通过氢化反应从相应的奥罗宁合成了这些二氢奥罗宁。对这些二氢奥罗宁及其对应的奥罗宁进行了抗氧化、抗炎和酪氨酸酶抑制活性的筛选。合成的二氢奥罗宁（3b-f）在超氧自由基清除实验中表现出比标准的没食子酸更优越的抗氧化活性。二氢奥罗宁（3b-f）还表现出显著的酪氨酸酶抑制活性，其中两种二氢奥罗宁（3h、3j）显示出有希望的5-脂氧酶抑制活性。

  DOI：

  10.14233/ajchem.2021.23139
• 作为产物：
  描述：

  [2-[2-Bromo-3-methoxy-3-(4-methoxyphenyl)propanoyl]-3,5-dimethoxyphenyl] acetate 在 氢氧化钾 、 水 作用下， 以 乙醇 为溶剂， 以85%的产率得到(Z)-4,6-dimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n -tetrabutylammonium tribromide

  摘要：

  A wide variety of aurones (3a-f) can be prepared exclusively from 2'-acetoxychalcones (1a-f) in high yields in two steps, by bromination using n-tetrabutylammonium tribromide (TBATB) in the presence of CaCO3 in CH2Cl2-MeOH (5:2) at 0-5 degreesC followed by cyclization of the brominated. products 2a-f on treating with 0.2 M ethanolic KOH solution at 0-5 degreesC, respectively. In contrast various flavone derivatives 6a-f can be obtained exclusively from compounds 1a-f in fairly good yields, by brominating with the same reagent in CH2Cl2, followed by dehydrobromination and finally cyclization on treating with 0.1 M NaOMe solution. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01938-4

文献信息

• Dimethoxyaurones: Potent inhibitors of ABCG2 (breast cancer resistance protein)
  作者：Hong-May Sim、Chong-Yew Lee、Pui Lai Rachel Ee、Mei-Lin Go

  DOI：10.1016/j.ejps.2008.07.008

  日期：2008.11

  their ability to modulate ABCG2 (breast cancer resistance protein)-mediated multidrug resistance in vitro. Several members (0.5 microM) increased the accumulation of mitoxantrone (MX) in human breast cancer cells (MDA-MB-231) transfected with ABCG2 and re-sensitized these cells to the cytotoxic effects of MX. In the re-sensitization assay, aurones at 0.5 microM reduced the resistance of the transfected

  通过将4，6-二甲氧基苯并呋喃-3（2H）-1与各种苯甲醛在碱催化的醛醇缩合反应中反应，合成了一系列4,6-二甲氧基金错误。根据光谱和晶体学数据将AZ构型分配给了光环。测试了金黄色素在体外调节ABCG2（乳腺癌抗性蛋白）介导的多药抗性的能力。几个成员（0.5 microM）增加了用ABCG2转染的人乳腺癌细胞（MDA-MB-231）中米托蒽醌（MX）的积累，并使这些细胞对MX的细胞毒性作用重新敏感。在再敏化试验中，0.5 microM的金黄色素使转染细胞对MX的抗性降至亲代细胞的两倍，超过在相同浓度下测试的泛黄霉素C（FTC）。金黄色素（10 microM）还增加了钙黄绿素-AM在用ABCB1（P-糖蛋白）转染的MDCKII / MDR1细胞中的蓄积，其水平与在相同浓度下测试的维拉帕米相当。结构活性分析表明，对于ABCG2抑制作用，金质模板中亚苄基环B的取代作用不那么重要，对于具有未取代环
• Unusual Olefinic C–H Functionalization of Simple Chalcones toward Aurones Enabled by the Rational Design of a Function-Integrated Heterogeneous Catalyst
  作者：Takafumi Yatabe、Xiongjie Jin、Noritaka Mizuno、Kazuya Yamaguchi

  DOI：10.1021/acscatal.8b00727

  日期：2018.6.1

  components of the catalyst: (a) a supported Pd catalyst: a catalyst for the olefinic C–H functionalization of chalcones toward aurones, (b) an Au promoter: an improvement in the catalytic activity by stabilizing Pd(0), (c) a CeO2 support: the inhibition of the 6-endo-trig cyclization utilizing the adsorption of chalcones, and (d) a Pd-on-Au structure: the inhibition of Au-catalyzed flavone synthesis. This catalytic

  黄酮类化合物是从查耳酮中获得的普遍存在的植物次生代谢产物，大部分具有源自6- endo-trig的6-元C环。查耳酮的环化。但是，作为一类类黄酮，很少天然出现的金黄色素具有主要通过进行B环氧化而从查耳酮生物合成的不寻常的5元C环。因此，从简单的查耳酮到金红石的化学催化转化是有吸引力的，因为它克服了已知的有限酶催化的缺点。然而，由于具有优先的6元环形成以及生物合成以及对罕见的分子内烯烃C–H官能化的需求，因此尚未报道催化转化。在这里，我们通过合理设计功能集成的非均相催化剂（负载在CeO上的Au上的Pd-on-Au双金属纳米颗粒催化剂），开发了简单的查耳酮对各种光环的催化烯烃C–H官能化2-在空气中使用O 2作为唯一氧化剂，不添加任何添加剂。在该系统中，催化剂的各个组成部分均实现了向金黄色挑战性转化所需的四个条件：（a）负载的Pd催化剂：查耳酮向CH的烯烃C-H官能化反应的催化剂，（b ）Au
• Metal-free methodology for the preparation of sterically hindered alkynoylphenols and its application to the synthesis of flavones and aurones
  作者：Cassandra Taylor、Yuri Bolshan

  DOI：10.1016/j.tetlet.2015.05.097

  日期：2015.7

  A metal-free synthesis for the preparation of sterically demanding ortho-demethylated ynones from mixed anhydrides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without the exclusion of air and moisture. This method is advantageous in that it is operationally simple, proceeds under mild conditions, and has a broad

  已经开发了一种无金属的合成方法，用于从混合酸酐和炔基三氟硼酸钾盐制备空间上要求的邻去甲基化的炔酮。在路易斯酸存在下，一锅法反应迅速进行，并且不排除空气和湿气。该方法的优点在于操作简单，在温和条件下进行并且具有广泛的基材范围。2，6-二甲氧基取代的酸酐以良好的收率提供了相应的单去甲基化的炔酮产物。特别地，2-羟基取代的炔酮产物是有价值的合成中间体，因为它们直接转化为具有生物活性的天然产物支架。经由的6-内环化反应，得到黄酮ö-炔基苯酚中间体在酸性条件下。发现碳酸铯可促进快速的5-exo环化，从而提供金酮产品。
• Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity
  作者：Anastasia Detsi、Maya Majdalani、Christos A. Kontogiorgis、Dimitra Hadjipavlou-Litina、Panagiotis Kefalas

  DOI：10.1016/j.bmc.2009.10.002

  日期：2009.12

  A series of 2'-hydroxy-chalcones and their oxidative cyclization products, aurones, have been synthesized and tested for their antioxidant and lipoxygenase inhibitory activity. The natural product aureusidin (31) was synthesized in high yield by a new approach. An extensive structure-relationship study was performed and revealed that several chalcones and aurones possess an appealing pharmacological profile combining high antioxidant and lipid peroxidation activity with potent soybean LOX inhibition. (C) 2009 Elsevier Ltd. All rights reserved.
• A One-Pot Synthesis of Aurones from Substituted Acetophenones and Benz­aldehydes: A Concise Synthesis of Aureusidin
  作者：Zhixiang Xie、Ying Li、Xiaolong Zhao、Jie Liu

  DOI：10.1055/s-0031-1291153

  日期：2012.7

  A one-pot synthesis of aurones from substituted acetophenone and benzaldehyde has been developed on the basis of an improved Algar-Flynn-Oyamada reaction. By using this method, several aurones were prepared in three steps from commercial starting materials. The usefulness of this one-pot strategy was confirmed by a synthesis of aureusidin, an inhibitor of iodothyronine deiodinase, in 41% overall yield. In comparison with a two-step synthesis of this product from the same substrates, the one-pot strategy was more effective, giving a higher yield and requiring fewer and simpler operations.