6-羟基-5,7-二甲氧基-2-苯基色烯-4-酮 | 119892-40-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 6-羟基-5,7-二甲氧基-2-苯基色烯-4-酮
• 英文名称: 6-hydroxy-5,7-dimethoxyflavone
• 英文别名: 6-hydroxy-5,7-dimethoxy-2-phenylchromen-4-one
• CAS: 119892-40-9
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: YLSUKCVZCXUJBF-UHFFFAOYSA-N

物化性质

• 熔点：
  204-206 °C
• 沸点：
  530.4±50.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-羟基-5,7-二甲氧基-2-苯基色烯-4-酮 在 氢溴酸 作用下， 以88%的产率得到黄芩素
  参考文献：
  名称：

  一种制备黄芩素的方法

  摘要：

  本发明公开了一种制备黄芩素的方法，该方法以2,6‑二甲氧基对苯醌为起始原料，经过还原、付克乙酰化、克莱森缩合、脱氢氧化环合以及脱甲基五步反应即可高收率制得黄芩素。该方法所用起始原料及试剂等均价廉易得，合成步骤较少，操作简单方便，易于生产控制，产物收率高，纯度好，适宜于黄芩素的大量制备和生产应用。

  公开号：

  CN105906599B
• 作为产物：
  描述：

  三溴苯酚 在 三氟化硼乙醚 、 碘 、 乙酸酐 、 copper(l) chloride 作用下， 以 甲醇 、 氯仿 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 52.0h， 生成 6-羟基-5,7-二甲氧基-2-苯基色烯-4-酮
  参考文献：
  名称：

  一种制备黄芩素的方法

  摘要：

  本发明涉及一种制备抗病毒和抗菌消炎药物黄芩素的方法，该方法以苯酚为起始原料，经过溴代、甲氧基取代、付克酰化、醇醛缩合反应制得关键查尔酮中间体；该关键中间体再经氧化环合及脱除甲基反应即可制得高纯度的黄芩素；该新方法所使用原料试剂均价廉易得，合成步骤少，反应操作简单方便，易于生产控制，产物收率高，纯度好，适宜于黄芩素的生产应用。

  公开号：

  CN105237503B

文献信息

• Studies of the Selective<i>O</i>-Alkylation and Dealkylation of Flavonoids. XVIII. A Convenient Method for Synthesizing 3,5,6,7-Tetrahydroxyflavones
  作者：Tokunaru Horie、Takashi Kobayashi、Yasuhiko Kawamura、Isao Yoshida、Hideaki Tominaga、Kazuyo Yamashita

  DOI：10.1246/bcsj.68.2033

  日期：1995.7

  In the demethylation of 6-hydroxy-3,4′,7-trimethoxy-5-(tosyloxy)flavone with anhydrous aluminum bromide, the 5-tosyloxyl group was eliminated with bromination to give 8-bromo-3,6,7-trihydroxy-4′-methoxyflavone as the main product. When anhydrous aluminum chloride was used in the demethylation of the acetate, the 5-tosyloxyl group was cleaved prior to the demethylation to give 5,6,7-trihydroxy-3,4′-dimethoxyflavone. Demethylation of 6-hydroxy-4′,5,7-trimethoxy-3-(tosyloxy)flavone and its acetate with the bromide or chloride afforded the 5,6,7-trihydroxyflavone without the cleavage of the 3-tosyloxyl group, but was not suitable for the general synthesis of the 3,5,6,7-tetrahydroxyflavones because of the difficulty in removing the protecting group. Consequently, it was found that the direct demethylation of 3,6-dihydroxy-5,7-dimethoxyflavones with anhydrous aluminum chloride–sodium iodide in acetonitrile was the most useful general method for synthesizing 3,5,6,7-tetrahydroxyflavones. Additionally, the reported structures of two natural flavones were revised.

  在无水溴化铝的脱甲基反应中，6-羟基-3,4′,7-三甲氧基-5-(托烯氧基)黄酮的5-托烯氧基基团在溴化作用下被消除，生成8-溴-3,6,7-三羟基-4′-甲氧基黄酮作为主要产物。当使用无水氯化铝进行醋酸酯的脱甲基反应时，5-托烯氧基基团在脱甲基前被切断，生成5,6,7-三羟基-3,4′-二甲氧基黄酮。6-羟基-4′,5,7-三甲氧基-3-(托烯氧基)黄酮及其醋酸酯与溴化物或氯化物的脱甲基反应生成5,6,7-三羟基黄酮，而不切断3-托烯氧基基团，但由于去除保护基团的困难，不适合于3,5,6,7-四羟基黄酮的一般合成。因此，发现采用无水氯化铝-碘化钠在乙腈中对3,6-二羟基-5,7-二甲氧基黄酮进行直接脱甲基反应是合成3,5,6,7-四羟基黄酮的最有效的一般方法。此外，修订了两种天然黄酮的已报告结构。
• Sastri; Seshadri, Proceedings - Indian Academy of Sciences, Section A, 1946, # 23, p. 273,276
  作者：Sastri、Seshadri

  DOI：——

  日期：——
• Use of acyl substituents to favour 2,3-epoxidation of 5,7-dioxygenated flavones with dimethyldioxirane
  作者：Benjamin J. Compton、Lesley Larsen、Rex T. Weavers

  DOI：10.1016/j.tet.2010.11.076

  日期：2011.1

  The reaction of 5,7-dimethoxyflavone with dimethyldioxirane (DMDO) gives the 2,3-epoxide rapidly at first. However, low levels of ring A hydroxylated by-products are also formed. With increasing proportions of DMDO, demethylation at C-5 becomes apparent and consumption of substrate is not matched by further significant build-up of the epoxide. Deactivation of ring A by the use of acyl groups removes this complication. 5,7-Diacylflavones give excellent yields of epoxides and monoacyl derivatives also react in good yield. Ionization potential mans derived from density functional theory calculations (B3LYP/6-31G*), provide good visual indicators of the relative reactivity of the key nucleophilic loci. The epoxides may be isolated as such, or transformed into flavonols by treatment with p-toluenesulfonic acid. (C) 2010 Elsevier Ltd. All rights reserved.
• Obtaining new flavanones exhibiting antifungal activities by methyltrioxorhenium-catalyzed epoxidation–methanolysis of flavones
  作者：Roberta Bernini、Enrico Mincione、Gianfranco Provenzano、Giancarlo Fabrizi、Sabrina Tempesta、Marcella Pasqualetti

  DOI：10.1016/j.tet.2008.05.101

  日期：2008.8

  New 3-hydroxy-2-methoxyflavanones have been obtained through epoxidation-methanolysis of the corresponding flavone with urea-hydrogen peroxide (UHP)/methyltrioxorhenium (CH3ReO3, MTO) catalytic system in methanol as nucleophilic solvent. After acetylation of the reaction mixtures, the corresponding cis- and trans-3-acetoxy-2-methoxyflavanones have been isolated and characterized by spectroscopic analyses. Their antifungal activity has been tested in vitro against three fungal strains of common saprotrophic soil and seed fungi, such as Trichoderma koningii, Fusarium solani and Cladosporium herbarum, potentially pathogenic for humans. Some aspects of the structure-activity relationship of the most active compounds have been evaluated. The mycelial growth of T. koningii and C. herbarum has been totally inhibited from cis-3-acetoxy-2,6-dimethoxyflavanone 7c and cis-3-acetoxy-2,7dimethoxyflavanone 13c at the lowest concentration (0.5x10(-4) M). (C) 2008 Elsevier Ltd. All rights reserved.
• A Novel Route to 5,7-Dimethoxy-6-hydroxyflavone
  作者：Mauricio Osorio-olivares、Bruce K. Cassels、Silvia Sepúlveda-Boza、Marcos Caroli Rezende

  DOI：10.1080/00397919908086038

  日期：1999.3

  A novel route to 5,7-dimethoxy-6-hydroxyflavone is described, involving the cyclization of an intermediate phosphorane as the key step.