7-hydroxy-3,3',4',5,5',8-hexamethoxyflavone | 110193-72-1

• 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: 7-hydroxy-3,3',4',5,5',8-hexamethoxyflavone
• 英文别名: 7-hydroxy-3,5,8-trimethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-one；7-Hydroxy-3,5,8-trimethoxy-2-(3,4,5-trimethoxy-phenyl)-chromen-4-on；7-hydroxy-3,5,8-trimethoxy-2-(3,4,5-trimethoxyphenyl)chromen-4-one
• CAS: 110193-72-1
• 化学式: C₂₁H₂₂O₉
• 分子量: 418.4
• InChiKey: IKCYYEMXLNWGDA-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C(Solv: acetic acid (64-19-7))
• 沸点：
  651.1±55.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  105.82
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  7-hydroxy-3,3',4',5,5',8-hexamethoxyflavone 在 氢碘酸 、 乙酸酐 作用下， 生成 hibiscetin
  参考文献：
  名称：

  Rao et al., Proceedings - Indian Academy of Sciences, Section A, 1944, # 19, p. 88,91

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4-dihydroxy-3,6,ω-trimethoxyacetophenone 生成 7-hydroxy-3,3',4',5,5',8-hexamethoxyflavone
  参考文献：
  名称：

  HORIE, TOKUNARU;TSUKAYAMA, MASAO;KAWAMURA, YASUHIKO;SENO, MASAMICHI, J. ORG. CHEM., 52,(1987) N 21, 4702-4709

  摘要：

  DOI：

文献信息

• Studies of the Selective<i>O</i>-Alkylation and Dealkylation of Flavonoids. XI. A New Convenient Method for Synthesizing 3,5,7-Trihydroxy-8-methoxyflavones from 7-Hydroxy-3,5,8-trimethoxyflavones
  作者：Tokunaru Horie、Masao Tsukayama、Yasuhiko Kawamura、Masamichi Seno、Shigeo Yamamoto

  DOI：10.1246/bcsj.61.441

  日期：1988.2

  The 3- or 5-methoxyl group in the ditosylates of 5,7-dihydroxy-3,4′,8-trimethoxy- and 3,7-dihydroxy-4′,5,8-trimethoxyflavones was quantitatively demethylated with anhydrous aluminum bromide in acetonitrile to give the corresponding monohydroxyflavones, which were easily hydrolyzed into 3,5,7-trihydroxy-4′,8-dimethoxyflavone. On the basis of the results, the following convenient method for synthesizing 3,5,7-trihydroxy-8-methoxyflavones from 7-hydroxy-3,5,8-trimethoxyflavones was established. 7-Hydroxy-3,5,8-trimethoxyflavones or their tosylates were demethylated with 5% w/v anhydrous aluminum bromide in acetonitrile to give a mixture of the corresponding 3- and 5-hydroxyflavones. The mixture was tosylated and the resultant mixture was demethylated under the same conditions. The demethylated products were hydrolyzed with anhydrous potassium carbonate in methanol to give the desired 3,5,7-trihydroxy-8-methoxyflavones in high yields.

  用无水溴化铝在乙腈中定量脱甲基，得到相应的单羟基黄酮，这些单羟基黄酮很容易水解成 3,5,7-三羟基-4′,8-二甲氧基黄酮。在此基础上，建立了以下从 7-羟基-3,5,8-三甲氧基黄酮合成 3,5,7-三羟基-8-甲氧基黄酮的简便方法。7- 羟基-3,5,8-三甲氧基黄酮或其对甲苯磺酸盐在乙腈中用 5% w/v 无水溴化铝脱甲基，得到相应的 3- 和 5- 羟基黄酮的混合物。在相同条件下，对混合物进行甲苯磺酰化，并对得到的混合物进行脱甲基处理。脱甲基产物在甲醇中用无水碳酸钾进行水解，以高产率得到所需的 3,5,7-三羟基-8-甲氧基黄酮。
• Studies of the selective O-alkylation and dealkylation of flavonoids. 10. Selective demethylation of 7-hydroxy-3,5,8-trimethoxyflavones with anhydrous aluminum halide in acetonitrile or ether
  作者：Tokunaru Horie、Masao Tsukayama、Yasuhiko Kawamura、Masamichi Seno

  DOI：10.1021/jo00230a009

  日期：1987.10
• 3,5-Dihydroxy-7,8-dimethoxyflavones and revised structures for some natural flavones
  作者：Tokunaru Horie、Masao Tsukayama、Yasuhiko Kawamura、Shigeo Yamamoto

  DOI：10.1016/0031-9422(88)80222-x

  日期：1988.1
• HORIE, TOKUNARU;TSUKAYAMA, MASAO;KAWAMURA, YASUHIKO;SENO, MASAMICHI;YAMAM+, BULL. CHEM. SOC. JAP., 61,(1988) N 2, 441-447
  作者：HORIE, TOKUNARU、TSUKAYAMA, MASAO、KAWAMURA, YASUHIKO、SENO, MASAMICHI、YAMAM+

  DOI：——

  日期：——