2-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-methoxyphenyl)ethanone | 27181-83-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-methoxyphenyl)ethanone
• 英文别名: 2,4,4',6-tetrahydroxy-3-methoxydeoxybenzoin；2,4,6,4'-tetrahydroxy-3-methoxy-deoxybenzoin；2,4,6,4'-Tetrahydroxy-3-methoxy-desoxybenzoin；4-Hydroxybenzyl-2,4,6-trishydroxy-3-methoxyphenylketon
• CAS: 27181-83-5
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: XESLVBOBZOCEFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  220-221.5 °C
• 沸点：
  504.4±19.0 °C(Predicted)
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-methoxyphenyl)ethanone 在 吡啶 、 喹啉 、 铜 、 sodium carbonate 、 丙酮 作用下， 生成 鸢尾黄素
  参考文献：
  名称：

  The Synthesis of 4′,5,7-Trihydroxy-8-methoxyisoflavone

  摘要：

  DOI：

  10.1246/bcsj.30.689
• 作为产物：
  描述：

  4-Hydroxybenzyl-4-benzyloxy-2,6-dihydroxy-3-methoxyphenylketon 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 生成 2-(4-hydroxyphenyl)-1-(2,4,6-trihydroxy-3-methoxyphenyl)ethanone
  参考文献：
  名称：

  异黄酮的合成。第五部分Irigenin和Tectorigenin

  摘要：

  合成异黄酮的一般乙氧基化方法已应用于合成irigenin（VII）和tectorigenin（XVI）。该合成途径也产生了异构体，ψ -irigenin（XI）和ψ -tectorigenin（XX）。讨论了有关某些乙氧基化反应中产物比例以及5,6,7-和5,7,8-三取代异黄酮的相对热力学稳定性的信息。

  DOI：

  10.1039/j39700001219

文献信息

• Polyphenols based on isoflavones as inhibitors of Helicobacter pylori urease
  作者：Zhu-Ping Xiao、Da-Hua Shi、Huan-Qiu Li、Li-Na Zhang、Chen Xu、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2007.03.045

  日期：2007.6.1

  Twenty polyphenols were synthesized and evaluated for their effect on Helicobacter pylori urease. Among these compounds, 4-(p-hydroxyphenethyl)pyrogallol (15) (IC50 = 0.03 mM) and 7,8,4'-trihydroxyisoflavone (19) (IC50 = 0.14 mM) showed potent inhibitory activities, and inhibited Helicobacter pylori urease in a time-dependent manner. The structure-activity relationship of these polyphenols revealed: the two ortho hydroxyl groups were essential for inhibitory activity of polyphenol. When the C-ring of isoflavone was broken, the inhibitory activity markedly decreased. As for deoxybenzoin, the carboxyl group was clearly detrimental. (c) 2007 Elsevier Ltd. All rights reserved.
• Efficient Method for the Synthesis of Tectorigenin
  作者：Zhu‐Ping Xiao、Huan‐Qiu Li、Jia‐Yu Xue、Lei Shi、Hai‐Liang Zhu

  DOI：10.1080/00397910701796725

  日期：2008.1.1

  Tectorigenin, isolated from the rhizomes of Belamcanda chinensis, shows a wide variety of biological activities. The interest in its biological activities has been matched by a corresponding interest in its synthesis. We herein reported a convenient synthesis of tectorigenin in good yield. The starting material, 2,4,6-trihydroxyanisole, gave the intermediate 2,4,4',6-tetrahydroxy-3-methoxydeoxybenzoin by a Hoesch reaction with 4-hydroxyphenylacetonitrile. The intermediate was then reacted with methanesulfonyl chloride to produce a mixture of tectorigenin and psi-tectorigenin. Purification of tectorigenin was unnecessary at this stage as psi-tectorigenin in the mixture was isomerized to tectorigenin by refluxing in n-BuOH in the presence of K2CO3.
• Amines and oximes derived from deoxybenzoins as Helicobacter pylori urease inhibitors
  作者：Huan-Qiu Li、Zhu-Ping Xiao、Yin-Luo、Tao Yan、Peng-Cheng Lv、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2008.06.001

  日期：2009.5

  Twenty amines and oximes from deoxybenzoins were prepared and evaluated for their inhibitory activity against Helicobacter pylori urease. Among these compounds, high inhibitory activities were observed in amines and oximes, especially amines 1b (IC50 = 0.011 mM) and 6b (IC50 = 0.047 mM) exhibited good in vitro activities, and were comparable to acetohydroxamic acid (AHA). The hydroxyl groups on deoxybenzoin skeleton may be responsible for the inhibitory activity and coordinate with the nickel (active site) on enzyme. A direct interaction may exist between the OH group of hydroxylamines or NH group of amines and His alpha 323 of H. pylori urease, which is on the flap of the enzyme active site. (C) 2008 Elsevier Masson SAS. All rights reserved.