汉黄芩素 | 4431-47-4

• 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: 汉黄芩素
• 中文别名: 苯酚,4-乙烯基-,聚合乙烯基苯
• 英文名称: 5,8-dihydroxy-7-methoxyflavone
• 英文别名: isowogonin；5,8-dihydroxy-7-methoxy-2-phenylchromen-4-one
• CAS: 4431-47-4
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: CGTZOVPQCMHAIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 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：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  汉黄芩素 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以95%的产率得到5,7,8-三羟基黄酮
  参考文献：
  名称：

  苏荠苧黄酮、异汉黄芩素和去甲汉黄芩素的合 成方法

  摘要：

  本发明公开一种苏荠苧黄酮的合成方法。该方法包括如下步骤，(1)5，7‑二甲氧基‑8‑溴‑黄酮在亚铜盐催化下与甲醇钠反应生成5，7，8‑三甲氧基黄酮；(2)惰性气氛下，5,7,8‑三甲氧基黄酮在三氯化铝作用下，反应得到苏荠苧黄酮。在该方法的基础上，可进一步对苏荠苧黄酮脱甲基，分别得到异汉黄芩素和去甲汉黄芩素。本发明起始原料来源丰富，选择性好，条件温和，获得苏芥苧黄酮、异汉黄芩素和去甲汉黄芩素的总产率分别为60％、58％和57％(以白杨素计)，合成的产品纯度大于99.0％，适合工业化生产。

  公开号：

  CN104926768B
• 作为产物：
  描述：

  白杨素 在 aluminum (III) chloride 、 N-溴代丁二酰亚胺(NBS) 、 三溴化硼 、 potassium carbonate 、 copper(ll) bromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 18.34h， 生成 汉黄芩素
  参考文献：
  名称：

  苏荠苧黄酮、异汉黄芩素和去甲汉黄芩素的合 成方法

  摘要：

  本发明公开一种苏荠苧黄酮的合成方法。该方法包括如下步骤，(1)5，7‑二甲氧基‑8‑溴‑黄酮在亚铜盐催化下与甲醇钠反应生成5，7，8‑三甲氧基黄酮；(2)惰性气氛下，5,7,8‑三甲氧基黄酮在三氯化铝作用下，反应得到苏荠苧黄酮。在该方法的基础上，可进一步对苏荠苧黄酮脱甲基，分别得到异汉黄芩素和去甲汉黄芩素。本发明起始原料来源丰富，选择性好，条件温和，获得苏芥苧黄酮、异汉黄芩素和去甲汉黄芩素的总产率分别为60％、58％和57％(以白杨素计)，合成的产品纯度大于99.0％，适合工业化生产。

  公开号：

  CN104926768B

文献信息

• Short-step syntheses of naturally occurring polyoxygenated aromatics based on site-selective transformation
  作者：Yasunobu Yamashita、Alan Biard、Kengo Hanaya、Mitsuru Shoji、Takeshi Sugai

  DOI：10.1080/09168451.2017.1303362

  日期：2017.7.3

  Wogonin and astringin were synthesized from inexpensive chrysin and piceid in short steps. The key feature of these syntheses is site-selective transformation. The target molecules were obtained in 27 and 62% yields from the starting materials, respectively.

  摘要：Wogonin和astringin是从廉价的芹菜素和白藜芦醇中经过简短步骤合成的。这些合成的关键特点是位点选择性转化。从起始材料中，目标分子分别以27%和62%的产率获得。
• Rao et al., Proceedings - Indian Academy of Sciences, Section A, 1947, # 25, p. 427,430
  作者：Rao et al.

  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.
• Insect Antifeedant Activity of Flavones and Chromones against <i>Spodoptera litura</i>
  作者：Masanori Morimoto、Kumiko Tanimoto、Sachiko Nakano、Takayoshi Ozaki、Ayako Nakano、Koichiro Komai

  DOI：10.1021/jf025627a

  日期：2003.1.1

  The antifeedant polymethylated flavones 5-hydroxy-3,6,7,8,4'-heptamethoxyflavone, 5-hydroxy-3,6,7,8-tetra methoxyflavone, and 5,6-dihydroxy-3,7-dimethoxyflavone have been isolated from the cudweed, Gnaphalium affine D. Don (Compositae). These flavonoids and authentic analogues showed insect antifeedant activity against the common cutworm (Spodoptera litura F.). In a previous paper, it was suggested that there was no substituent on the B-ring of the flavonoid for the beneficial antifeedant activity against the common cutworm. These flavonoids having a phenyl group as the B-ring and the chromone as elimination of the B-ring from the flavonoids were used to test the hypothesis of the previously described B-ring effect. The known fact is that Sculletaria baicarensis (Rutaceae) produced the 2-phenyl flavone. Test compounds and their methylated derivatives were prepared from this material for the structure-activity relationship (SAR) study of insect antifeedant activity. In spite of the 2-phenyl flavonoids, some tested compounds did not show any insect antifeedant activity against the common cutworm, although these inactive flavonoids were deficient in the 6-substituent group on the A-ring of the flavonoid. This 6-position-substituted derivative almost showed strong insect antifeedant activity against common cutworm. Moreover, the tested flavonoids having a hydroxyl group as a substituent on any of the positions tended to increase the activity. These results suggested the importance of the 6-position substitution on the flavonoid; however, hydrophilic substituents decreased the activity. Baicalein (5,6,7-trihydroxyflavone) derivatives did not show any activity despite having the 6-substituent derivative. Although the activity of some chromones increased the activity of the flavone, the bulky B-ring was a disadvantage for the antifeedant activity. It was suggested that the charge on C(3) and C(5) of the flavonoid was important for the biological activity. Additionally, an adequate hydrogen bonding property, which is different from lipophilicity, was an advantage for the activity on the basis of a QSAR analysis.