5,7,8-Trihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one

• 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: 5,7,8-Trihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one
• 英文别名: 5,7,8-Trihydroxy-3,4'-dimethoxyflavone；5,7,8-trihydroxy-3-methoxy-2-(4-methoxyphenyl)chromen-4-one
• 化学式: C₁₇H₁₄O₇
• 分子量: 330.294
• InChiKey: VKDBWLYSNXBRNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 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：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  7-benzyloxy-5,8-dihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one 在 palladium on activated charcoal 氢气 作用下， 生成 5,7,8-Trihydroxy-3-methoxy-2-(4-methoxy-phenyl)-chromen-4-one
  参考文献：
  名称：

  13C NMR spectral assignment of the A-ring of polyoxygenated flavones

  摘要：

  The C-13 NMR spectra of polyhydroxyflavones were systematically examined by using about 70 examples which have a 4-methoxyphenyl B-ring, such as 5,6,7-, 5,7,8 and 5,6,8-trioxygenated and 5,6,7,8-tetraoxygenated flavones and flavonols, and the following results were obtained. In the C-13 NMR spectra of flavones, the signals at the 2-, 3- and 4-positions in the C-ring were hardly affected by the substituents on the A-ring except for those at the 5-position and shifted regularly by introduction of a methoxy or hydroxy group at the 3-position. The signals at the 5- to 10-positions in the A-ring were greatly affected by the substituents and oxygenated patterns on the A-ring and exhibited the respective characteristic pattern reflecting the A-ring substituents without the effects of the substituents on the B- and C-rings. The substituent effects on the A-ring were estimated from the spectral data. Consequently, it is found that the structures of polyhydroxyflavones can be correctly defined by their C-13 NMR spectral assignment. Additionally, we examined the structures of some natural flavones previously reported. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(97)00629-8

文献信息

• 13C NMR spectral assignment of the A-ring of polyoxygenated flavones
  作者：Tokunaru Hòrie、Yoshizumi Ohtsuru、Kenichi Shibata、Kazuyo Yamashita、Masao Tsukayama、Yasuhiko Kawamura

  DOI：10.1016/s0031-9422(97)00629-8

  日期：1998.3

  The C-13 NMR spectra of polyhydroxyflavones were systematically examined by using about 70 examples which have a 4-methoxyphenyl B-ring, such as 5,6,7-, 5,7,8 and 5,6,8-trioxygenated and 5,6,7,8-tetraoxygenated flavones and flavonols, and the following results were obtained. In the C-13 NMR spectra of flavones, the signals at the 2-, 3- and 4-positions in the C-ring were hardly affected by the substituents on the A-ring except for those at the 5-position and shifted regularly by introduction of a methoxy or hydroxy group at the 3-position. The signals at the 5- to 10-positions in the A-ring were greatly affected by the substituents and oxygenated patterns on the A-ring and exhibited the respective characteristic pattern reflecting the A-ring substituents without the effects of the substituents on the B- and C-rings. The substituent effects on the A-ring were estimated from the spectral data. Consequently, it is found that the structures of polyhydroxyflavones can be correctly defined by their C-13 NMR spectral assignment. Additionally, we examined the structures of some natural flavones previously reported. (C) 1998 Elsevier Science Ltd. All rights reserved.