2'-hydroxyflavilium tetrafluoroborate | 1006623-69-3

• 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: 2'-hydroxyflavilium tetrafluoroborate
• 英文别名: 2′-hydroxyflavylium tetrafluoroborate
• CAS: 1006623-69-3
• 化学式: BF₄*C₁₅H₁₁O₂
• 分子量: 310.056
• InChiKey: ZIHZHZRFVLDKDO-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  5.39
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.53
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2'-hydroxyflavilium tetrafluoroborate 在 sodium hydroxide 、 水 作用下， 生成 trans-2,2'-dihydroxychalcone
  参考文献：
  名称：

  2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions

  摘要：

  Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2' cyclize to form flavanones in basic media. By synthesizing 2'-hydroxyflavylium tetrafluoroborate, it was possible to obtain trans-2,2'-dihydroxychalcone that in solution can evolve to 2'-hydroxyflavanone or back to 2'-hydroxyflavylium depending on the pH. The several equilibria established in aqueous solution were fully characterized. The importance of including flavanones into the flavylitun network of chemical reactions is briefly exploited. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.007
• 作为产物：
  描述：

  2'-羟基苯乙酮 、 水杨醛 在 tetrafluoroboric acid 、 乙酸酐 、 溶剂黄146 作用下， 以16.3%的产率得到2'-hydroxyflavilium tetrafluoroborate
  参考文献：
  名称：

  2′-Hydroxyflavylium: introducing flavanones into the flavylium network of chemical reactions

  摘要：

  Chalcones possessing a hydroxyl group in position 2 cyclize to form flavylium salts in acidic media, this reaction being reversible under neutral-basic conditions. On the other hand, chalcones possessing a hydroxyl group in position 2' cyclize to form flavanones in basic media. By synthesizing 2'-hydroxyflavylium tetrafluoroborate, it was possible to obtain trans-2,2'-dihydroxychalcone that in solution can evolve to 2'-hydroxyflavanone or back to 2'-hydroxyflavylium depending on the pH. The several equilibria established in aqueous solution were fully characterized. The importance of including flavanones into the flavylitun network of chemical reactions is briefly exploited. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.11.007

文献信息

• On the multistate of 2′-hydroxyflavylium-flavanone system. Illustrating the concept of a timer with reset at the molecular level
  作者：Stoyanka Slavcheva、Johan Mendoza、Stanislav Stanimirov、Ivan Petkov、Nuno Basílio、Fernando Pina、Vesselin Petrov

  DOI：10.1016/j.dyepig.2018.05.066

  日期：2018.11

  The multistate of species regarding 2'-hydroxyflavylium derivatives have a peculiar behavior due to the formation in moderately basic solutions of a flavanone from the mono-ionized trans-chalcone. The firmly established theory to account for the thermodynamics and kinetics of the flavylium based multistate of species in acidic medium was extended to the basic medium. The key experimental procedure to carry out this study is a sequence of reverse pH jumps from all pH range to a final pH sufficiently acid to have flavylium cation as the sole species. The reverse pH jumps can be performed from the equilibrium and pseudo-equilibrium. Acidification of the flavanone to pH = 1 does not give back flavylium cation. In contrast, the di-ionized species trans-chalcone is obtained in a very fast process from the flavanone at pH > 12. A cycle constituted by a sequence of pH jumps illustrates the concept of a timer at the molecular level with reset capacity.