3'-hydroxyaucuparin | 1204502-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3'-hydroxyaucuparin
• 英文别名: 3'',5''-Dimethoxybiphenyl-3,4''-diol；4-(3-hydroxyphenyl)-2,6-dimethoxyphenol
• CAS: 1204502-40-8
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: OPADYWJSAHKMJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3'-benzyloxy-3,4,5-trimethoxybiphenyl 在 magnesium iodide 作用下， 反应 6.0h， 以76%的产率得到3'-hydroxyaucuparin
  参考文献：
  名称：

  无溶剂条件下碘化镁对芳基醚的选择性脱甲基和脱苄基反应及其在天然产物的全合成中的应用†

  摘要：

  一种使用芳基甲基/苄基醚的有效选择性脱甲基和脱苄基方法 碘化镁 在无溶剂条件下已开发并应用于天然的合成 黄酮和联苯糖苷。在反应条件下可以耐受包括糖苷在内的多种官能团。实验结果表明，无论它们是在羰基的间位还是对位，O-苄基的去除都比O-甲基的去除更容易。因此，对于同时带有苄氧基和甲氧基的底物可以实现选择性的脱苄基作用。

  DOI：

  10.1039/b916969e

文献信息

• Design and synthesis of biphenyl derivatives as mushroom tyrosinase inhibitors
  作者：Kai Bao、Yi Dai、Zhi-Bin Zhu、Feng-Juan Tu、Wei-Ge Zhang、Xin-Sheng Yao

  DOI：10.1016/j.bmc.2010.07.062

  日期：2010.9

  of biphenyls, analogs of aglycone of natural product fortuneanoside E, were prepared using Suzuki–Miyaura cross-coupling and selective magnesium iodide demethylation/debenzylation, and their mushroom tyrosinase inhibitory activity was evaluated. Most of the 4-hydroxy-3,5-dimethoxyphenyl biphenyl compounds (series II, 20–36) were in general more active than 3,4,5-trimethoxyphenyl biphenyl compounds (series

  使用铃木-Miyaura交叉偶联和选择性碘化镁去甲基/去苄基作用，制备了两个新的联苯系列，即天然产物苦瓜子苷E糖苷配基类似物，并评估了其对蘑菇酪氨酸酶的抑制活性。通常，大多数4-羟基-3,5-二甲氧基苯基联苯化合物（II系列，20–36）比3,4,5-三甲氧基苯基联苯基化合物（I，1-19）更具活性。结构-活性关系研究表明，单糖取代基（例如葡萄糖）不是必需的，并且4-羟基-3,5-二甲氧基苯基部分的存在对于抑制活性至关重要。在合成的化合物中，化合物21（IC 50 = 0.02 mM）是活性最高的一种，其活性比金银花皂苷E（IC 50  = 0.14 mM）高7倍，比熊果苷（IC 50  = 0.21 mM）高10倍，被称为有效的酪氨酸酶抑制剂。通过Lineweaver-Burk图分析的抑制动力学表明，化合物21是竞争性抑制剂（K i  = 0.015 mM）。
• Selective demethylation and debenzylation of aryl ethers by magnesium iodide under solvent-free conditions and its application to the total synthesis of natural products
  作者：Kai Bao、Aixue Fan、Yi Dai、Liang Zhang、Weige Zhang、Maosheng Cheng、Xinsheng Yao

  DOI：10.1039/b916969e

  日期：——

  An efficient selective demethylation and debenzylation method for aryl methyl/benzyl ethers using magnesium iodide under solvent-free conditions has been developed and applied to the synthesis of natural flavone and biphenyl glycosides. A variety of functional groups including glycoside were tolerated under the reaction conditions. Experimental results indicated that the removal of an O-benzyl group

  一种使用芳基甲基/苄基醚的有效选择性脱甲基和脱苄基方法 碘化镁 在无溶剂条件下已开发并应用于天然的合成 黄酮和联苯糖苷。在反应条件下可以耐受包括糖苷在内的多种官能团。实验结果表明，无论它们是在羰基的间位还是对位，O-苄基的去除都比O-甲基的去除更容易。因此，对于同时带有苄氧基和甲氧基的底物可以实现选择性的脱苄基作用。
• Suzuki–Miyaura Coupling of Halophenols and Phenol Boronic Acids: Systematic Investigation of Positional Isomer Effects and Conclusions for the Synthesis of Phytoalexins from Pyrinae
  作者：Bernd Schmidt、Martin Riemer

  DOI：10.1021/jo500675a

  日期：2014.5.2

  The Suzuki-Miyaura couplings of o-, m-, and p-halophenols with o-, m-, and p-phenol boronic acids were investigated for all combinations under standardized conditions, using Pd/C as a heterogeneous catalyst and water as a solvent. In the case of iodophenols, conventional heating was used, while for bromophenols significantly better results could be obtained using microwave irradiation. This systematic study revealed that 2,4'-biphenol is particularly difficult to access, irrespective of the starting materials used, but that these difficulties can be overcome by using different additives. The conclusions drawn from this investigation allowed us to identify conditions for the protecting group-free or minimized total synthesis of biaryl-type phytoalexins. These compounds possess antibacterial activity and are produced by fruit trees as a response to microbial infection.
• Formation and exudation of biphenyl and dibenzofuran phytoalexins by roots of the apple rootstock M26 grown in apple replant disease soil
  作者：Belnaser A. Busnena、Till Beuerle、Felix Mahnkopp-Dirks、Traud Winkelmann、Ludger Beerhues、Benye Liu

  DOI：10.1016/j.phytochem.2021.112972

  日期：2021.12