(Z)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one | 23053-69-2

• 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)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one
• 英文别名: (Z)-2-[(3,4-dimethoxyphenyl)methylene]-4,6-dimethoxy-3(2H)-benzofuranone；(Z)-4,6,3',4'-tetramethoxyaurone；3',4,4',6-tetramethoxyaurone；4,6,3',4'-Tetramethoxyaurone；2-(3,4-dimethoxy-benzylidene)-4,6-dimethoxy-benzofuran-3-one；4,6-dimethoxy-2-((Z)-veratrylidene)-benzofuran-3-one；(2Z)-2-[(3,4-dimethoxyphenyl)methylidene]-4,6-dimethoxy-1-benzofuran-3-one
• CAS: 23053-69-2
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: CVKDSGICIOMAGA-IUXPMGMMSA-N

物化性质

• 熔点：
  175 °C
• 沸点：
  545.6±50.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 金色草素
  参考文献：
  名称：

  制备4，6,3'，4'-四取代噢哢经由氧化铝催化缩合

  摘要：

  通过保护-脱保护途径，以3（2）H-苯并呋喃酮与取代的醛的氧化铝催化缩合反应，制备了4,6,3'，4'-四取代的金氧烷，这是关键步骤。金黄色素（6）是通过4,6,3'，4'-四甲氧基甲隆（5）的甲基化获得的，这是一种天然的香附子。在一个加氢-脱保护步骤中，将4,6,3'，4'-四苄氧基金龙酮（9）转化为二氢金葡糖苷（10）。

  DOI：

  10.1002/jhet.5570420721
• 作为产物：
  描述：

  2-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone 在 sodium hydroxide 、 potassium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 (Z)-2-(3,4-dimethoxybenzylidene)-4,6-dimethoxybenzofuran-3(2H)-one
  参考文献：
  名称：

  Sharma, Anil; Chibber, S. S., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 275 - 277

  摘要：

  DOI：

文献信息

• Reactions of Carbanions with 1,3-Benzodioxin-4-ones: Facile Routes to Flavones, Aurones, and Acyl Phloroglucinols
  作者：George Kraus、Jingqiang Wie、Aniket Thite

  DOI：10.1055/s-2008-1078597

  日期：2008.8

  Two 1,3-benzodioxin-4-ones react with enolates, acetylides and aryllithium reagents to afford adducts that were converted into flavones, aurones, and an acyl phloroglucinol.

  两个1,3-苯并二噁烷-4-酮与烯醇盐、乙炔负离子和芳基锂试剂反应，生成的加合物进一步转化为黄酮、金黄色素和一种酰基苯酚。
• Versatile and Expeditious Synthesis of Aurones via Au^I-Catalyzed Cyclization
  作者：Hassina Harkat、Aurélien Blanc、Jean-Marc Weibel、Patrick Pale

  DOI：10.1021/jo702197b

  日期：2008.2.1

  Aurones are conveniently formed in a three-step procedure including a goldI-catalyzed cyclization of 2-(1-hydroxyprop-2-ynyl)phenols as a highly regio- and stereoselective key step. A wide diversity of derivatives can be obtained starting from substituted salicylaldehydes. Synthesis of natural 4,6,3‘,4‘-tetramethoxyaurone and structure revision of two natural products (dalmaisione D and 4‘-chloroaurone)

  可以以三步程序方便地形成Aurones，包括金I催化的2-（1-羟基丙-2-炔基）苯酚的环化反应，这是高度区域选择性和立体选择性的关键步骤。从取代的水杨醛开始可以得到各种各样的衍生物。实现了天然4,6,3'，4'-四甲氧基金龙的合成和两种天然产物（dalmaisione D和4'-氯金龙）的结构修饰。
• Discovery of Naturally Occurring Aurones That Are Potent Allosteric Inhibitors of Hepatitis C Virus RNA-Dependent RNA Polymerase
  作者：Romain Haudecoeur、Abdelhakim Ahmed-Belkacem、Wei Yi、Antoine Fortuné、Rozenn Brillet、Catherine Belle、Edwige Nicolle、Coralie Pallier、Jean-Michel Pawlotsky、Ahcène Boumendjel

  DOI：10.1021/jm200242p

  日期：2011.8.11

  We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC(50) below 5 mu M and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indo1-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC(50) of 2.2 mu M. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.
• Synthesis and Insect Antifeedant Activity of Aurones against <i>Spodoptera litura</i> Larvae
  作者：Masanori Morimoto、Hiromi Fukumoto、Toki Nozoe、Ai Hagiwara、Koichiro Komai

  DOI：10.1021/jf062562t

  日期：2007.2.1

  A series of aurones were prepared from various phenols via phenoxy acetic acids and coumaranones and evaluated for insect antifeedant activity against the common cutworm (Spodoptera litura). The naturally occurring aurone was most active at an ED50 of 0.12 mu mol/cm(2). The synthetic precursor, coumaranones, showed that the introduction of methoxyl and methyl groups to the benzene ring increased insect antifeedant activity. Similarly, the tested aurones showed that the introduction of methoxyl group to the A and/or B rings increased the insect antifeedant activity, but 4,5,6- and 3',4',5'-trisubstituted compounds did not show this activity in this test. The hydroxylation of aurones in the B ring should be disadvantageous for insect antifeedant activity against S. litura. Although the melting points did not correlate well with the insect antifeedant activity, compounds that were nearly inactive had high melting points. A significant correlation was noted between biological activity (pED(50)) and a hydrogen-bonding parameter calculated from the R-f value obtained from SiOH thin-layer chromatography and a lipophilicity parameter (log k) calculated from the retention time in ODS high-performance liquid chromatography. The respective correlation coefficients (r) were -0.83 and -0.70. The introduction of alkoxy and alkyl groups along with adequate hydrogen bonding seems to contribute to the antifeedant activity of the compounds tested.
• An environmentally benign synthesis of aurones and flavones from 2′-acetoxychalcones using n -tetrabutylammonium tribromide
  作者：Gopal Bose、Ejabul Mondal、Abu T Khan、Manob J Bordoloi

  DOI：10.1016/s0040-4039(01)01938-4

  日期：2001.12

  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.