2-(4-hydroxyphenyl)-3,4-dimethoxyacetophenone

• 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)-3,4-dimethoxyacetophenone
• 英文别名: 3,4-dimethoxyl-4'-hydroxyldeoxybenzoin；1-(3,4-Dimethoxyphenyl)-2-(4-hydroxyphenyl)ethanone；1-(3,4-dimethoxyphenyl)-2-(4-hydroxyphenyl)ethanone
• 化学式: C₁₆H₁₆O₄
• 分子量: 272.301
• InChiKey: FIQBYUMTDKEUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-hydroxyphenyl)-3,4-dimethoxyacetophenone 在 aluminum (III) chloride 、 二甲基硫 、 三氟化硼乙醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 生成 4’,6,7-三羟异黄酮
  参考文献：
  名称：

  Facile Method for the Large-Scale Synthesis of 6,7,4′-Trihydroxyisoflavanone

  摘要：

  6,7,4 '-Trihydroxyisoflavanone, the main source of which is extracted from soybeans, has been found to have diverse significant bioactivities. A large-scale, cost-effective, and facile chemical synthesis of 6,7,4 '-trihydroxyisoflavanone is presented herein. Its synthesis is characterized by three steps with an overall yield of 71% and a purity or more than 99.0%. This reaction can be scaled up to multikilogram quantities, providing a solid basis for its further bioactivity studies and drug development. With this same method, 6,7,3 ',4 '-tetrahydroxyisoflavanone, an analog of 6,7,4 '-trihydroxyisoflavanone, also can be largely prepared, indicating this modified synthetic method is potentially available for large-scale synthesis of a broad range of multihydroxyl isoflavanones.

  DOI：

  10.1080/00397911.2014.886331
• 作为产物：
  描述：

  3,4-二甲氧基苯酚 、 对羟基苯乙腈 在 盐酸 、 zinc(II) chloride 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 27.0h， 以85%的产率得到2-(4-hydroxyphenyl)-3,4-dimethoxyacetophenone
  参考文献：
  名称：

  Facile Method for the Large-Scale Synthesis of 6,7,4′-Trihydroxyisoflavanone

  摘要：

  6,7,4 '-Trihydroxyisoflavanone, the main source of which is extracted from soybeans, has been found to have diverse significant bioactivities. A large-scale, cost-effective, and facile chemical synthesis of 6,7,4 '-trihydroxyisoflavanone is presented herein. Its synthesis is characterized by three steps with an overall yield of 71% and a purity or more than 99.0%. This reaction can be scaled up to multikilogram quantities, providing a solid basis for its further bioactivity studies and drug development. With this same method, 6,7,3 ',4 '-tetrahydroxyisoflavanone, an analog of 6,7,4 '-trihydroxyisoflavanone, also can be largely prepared, indicating this modified synthetic method is potentially available for large-scale synthesis of a broad range of multihydroxyl isoflavanones.

  DOI：

  10.1080/00397911.2014.886331

文献信息

• The synthesis, structure and activity evaluation of pyrogallol and catechol derivatives as Helicobacter pylori urease inhibitors
  作者：Zhu-Ping Xiao、Tao-Wu Ma、Wei-Chang Fu、Xiao-Chun Peng、Ai-Hua Zhang、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2010.08.015

  日期：2010.11

  Some pyrogallol and catechol derivatives were synthesized, and their urease inhibitory activity was evaluated by using acetohydroxamic acid (AHA), a well known Helicobacter pylori urease inhibitor, as positive control. The assay results indicate that many compounds have showed potential inhibitory activity against H. pylori urease. 4-(4-Hydroxyphenethyl)phen-1,2-diol (2a) was found to be the most potent

  合成了一些邻苯三酚和邻苯二酚衍生物，并使用众所周知的幽门螺杆菌脲酶抑制剂乙酰氧肟酸（AHA）作为阳性对照，评估了它们对脲酶的抑制活性。测定结果表明许多化合物已显示出对幽门螺杆菌脲酶的潜在抑制活性。已发现4-（4-羟基苯乙基）phen-1,2-二醇（2a）是最有效的脲酶抑制剂，提取分数的IC 50值为1.5±0.2μM，完整细胞的IC 50值为4.2±0.3μM，至少10分别比AHA低2倍和20倍（IC 50为17.2±0.9μM，100.6±13μM）。这一发现表明2a潜在的脲酶抑制剂将值得进一步研究。为了理解所观察到的良好活性，进行了2a到幽门螺杆菌脲酶活性位点的分子对接。
• Generation and Reactivity of Ketyl Radicals with Lignin Related Structures. On the Importance of the Ketyl Pathway in the Photoyellowing of Lignin Containing Pulps and Papers
  作者：Claudia Fabbri、Massimo Bietti、Osvaldo Lanzalunga

  DOI：10.1021/jo047826u

  日期：2005.4.1

  the photochemical studies ketyl radicals have been produced by charge-transfer (CT) photoactivation of the electron donor−acceptor salts of methyl viologen (MV2+) with α-hydroxy-α-phenoxymethyl-aryl acetates. This process leads to the instantaneous formation of the reduced acceptor (methyl viologen radical cation, MV+•), as is clearly shown in a laser flash photolysis experiment by the two absorption

  通过辐射化学和光化学技术已经产生了具有木质素相关结构的酮基。在以前的研究中，酮基是通过α-羰基-β-芳基醚木质素模型与pH值为6.0的水溶液的脉冲辐射分解产生的溶剂化电子反应生成的。酮基的紫外-可见光谱的特征在于三个主要吸收带。当在碱性溶液（pH 11.0）中记录光谱时，这些谱带的形状和位置略有变化，现在将它们分配给了酮基自由基阴离子，并确定了1-（3,4,5-三甲氧基苯基）的ap K a = 9.5。 -2-苯氧基乙醇-1-基。发现酮基的衰变速率与剂量有关，在低剂量时，其范围为（1.7-2.7）×10 3 s- 1。在存在氧气的情况下，观察到酮基的快速衰变（k 2 = 1.8-2.7×10 9 M - 1 s - 1），伴随而来的是形成稳定的产物，即起始酮。在光化学研究中，已经通过α-羟基-α-苯氧基甲基-芳基乙酸酯的甲基紫精（MV 2+）的电子给体-受体盐的电荷转移（CT）光活化产生了
• Facile Method for the Large-Scale Synthesis of 6,7,4′-Trihydroxyisoflavanone
  作者：Jing Liu、Zhangyou Yang、Shenglin Luo、Yuhui Hao、Jiong Ren、Yongping Su、Weidong Wang、Rong Li

  DOI：10.1080/00397911.2014.886331

  日期：2014.11.17

  6,7,4 '-Trihydroxyisoflavanone, the main source of which is extracted from soybeans, has been found to have diverse significant bioactivities. A large-scale, cost-effective, and facile chemical synthesis of 6,7,4 '-trihydroxyisoflavanone is presented herein. Its synthesis is characterized by three steps with an overall yield of 71% and a purity or more than 99.0%. This reaction can be scaled up to multikilogram quantities, providing a solid basis for its further bioactivity studies and drug development. With this same method, 6,7,3 ',4 '-tetrahydroxyisoflavanone, an analog of 6,7,4 '-trihydroxyisoflavanone, also can be largely prepared, indicating this modified synthetic method is potentially available for large-scale synthesis of a broad range of multihydroxyl isoflavanones.