5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | 148356-24-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
• 英文别名: 5-hydroxy-3-(4-hydroxy-phenyl)-chromen-4-one；7,4'-dihydroxyisoflavanone；4',5-dihydroxyisoflavone；5,4'-dihydroxyflavone；genistein；daidzein；5-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 148356-24-5
• 化学式: C₁₅H₁₀O₄
• 分子量: 254.242
• InChiKey: GTKATHVTDOTYMV-UHFFFAOYSA-N

物化性质

• 沸点：
  486.0±45.0 °C(Predicted)
• 密度：
  1.443±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one 在 palladium on activated charcoal 氢气 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 20.0~60.0 ℃ 、206.84 kPa 条件下， 反应 4.0h， 生成 5-Hydroxy-3-(4-hydroxy-phenyl)-chroman-4-one
  参考文献：
  名称：

  Structural requirement of isoflavonones for the inhibitory activity of interleukin-5

  摘要：

  Sophoricoside isolated from Sophora japonica is a glycoside of isoflavonone as an inhibitor of interleukin (IL)-5. To identify structural requirements of this isoflavonone for its inhibitory activity against IL-5, isoflavonones, isoflavanones, and their glycosides were prepared and their inhibitory activity was tested against IL-5. Among them, 5-benzyloxy-3-(4-hydroxyphenyl)chromen-4-one (4b, 87.9% inhibition at 50 muM, IC50 = 15.3 muM) shows the most potent activity, comparable with that of sophoricoside. The important structural requirements of these isoflavonone analogs exhibiting the inhibitory activity against IL-5 were recognized as (1) planarity of chromen-4-one ring, (2) existence of phenolic hydroxyl at 4-position of B ring, and (3) introduction of benzyloxy at 5-position, which may act as a bulky group for occupying hydrophobic pocket in putative binding site. However the glucopyranosyl moiety of sophoricoside is not an essential motif for the activity. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00064-3
• 作为产物：
  描述：

  2',6'-二(苄氧基)苯乙酮 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 thallium(I) nitrate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 26.0h， 生成 5-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
  参考文献：
  名称：

  Nishiyama, Kiyotoshi; Esaki, Sachiko; Deguchi, Ikuko, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 1, p. 107 - 114

  摘要：

  DOI：

文献信息

• Novel Synthesis of 3-Phenyl-chromen-4-ones Using N-Heterocyclic Carbene as Organocatalyst: An Efficient Domino Catalysis Type Approach
  作者：Priya Mishra、Sarita Singh、Preyas Ankit、Shahin Fatma、Divya Singh、Jagdamba Singh

  DOI：10.5012/bkcs.2013.34.4.1070

  日期：2013.4.20

  Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.

  本文报道了一种简单高效的异黄酮合成方法，以各种取代的苯乙酮溴化物和邻香草醛在NHC存在下进行。该机制涉及消耗和再生催化剂的双催化循环的级联催化方法。该方法证明非常高效，产率很高。这里描述的方法代表了经典方法的一种环境友好的替代方案。
• An Efficient “One Pot” Synthesis of Isoflavones
  作者：Sreenivasan Balasubramanian、Muraleedharan G. Nair

  DOI：10.1080/00397910008087343

  日期：2000.2

  presence of BF3.Et2O followed by its treatment at room temperature with N, N'-dimethyl (chloromethylene) ammonium chloride, generated by reacting PCl5 with DMF provides a mild and efficient route for a “one pot” synthesis of Isoflavones in high yields.

  摘要 在 BF3.Et2O 存在下，由苯乙酸 1 和苯酚 2 初步形成脱氧苯偶姻 3，然后在室温下用 N, N'-二甲基（氯亚甲基）氯化铵处理，由 PCl5 与 DMF 反应生成，提供温和的高产率的“一锅法”合成异黄酮的有效途径。
• Development of a general approach to the synthesis of a library of isoflavonoid derivatives
  作者：Kyle F. Biegasiewicz、James S. Gordon、Deana A. Rodriguez、Ronny Priefer

  DOI：10.1016/j.tetlet.2014.07.110

  日期：2014.9
• Balasubramanian, Sreenivasan; Ward, Donald L.; Nair, Muraleedharan G., Journal of the Chemical Society. Perkin transactions I, 2000, vol. 4, p. 567 - 570
  作者：Balasubramanian, Sreenivasan、Ward, Donald L.、Nair, Muraleedharan G.

  DOI：——

  日期：——
• ENZYMES CATALYZING THE GLYCOSYLATION OF POLYPHENOLS
  申请人：Universität Hamburg

  公开号：EP3004336B1

  公开（公告）日：2017-03-29