2',3',4'-trimethoxyflavone | 7143-46-6

• 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',3',4'-trimethoxyflavone
• 英文别名: 2-(2,3,4-Trimethoxyphenyl)-4H-chromen-4-one；2-(2,3,4-trimethoxyphenyl)chromen-4-one
• CAS: 7143-46-6
• 化学式: C₁₈H₁₆O₅
• 分子量: 312.322
• InChiKey: OELSHBWAOILUHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  458.7±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2',3',4'-trimethoxyflavone 在 硫酸 作用下， 反应 5.0h， 以90%的产率得到2',3',4'-trihydroxyflavone-5'-sulfonic acid
  参考文献：
  名称：

  Demethylation-Sulfonation of 2',3',4'-Trimethoxyflavones

  摘要：

  Total demethylation of 2',3',4'-trimethoxyflavones with sulfuric acid was realised at mild temperature giving respective 2',3', 4'-trihydroxyflavone-5'-sulfonic acids. A multi steps mechanism is proposed in the light of earlier results and the complete assignment of the H-1 and C-13 NMR spectra of a suggested 3'-hydroxy-2',4'-dimethoxy intermediate.

  DOI：

  10.3987/com-99-8546
• 作为产物：
  描述：

  (E)-1-(2-Hydroxy-phenyl)-3-(2,3,4-trimethoxy-phenyl)-propenone 在 ruthenium(III) chloride trihydrate 作用下， 反应 5.0h， 以225 mg的产率得到2',3',4'-trimethoxyflavone
  参考文献：
  名称：

  一种新型的一锅法合成黄酮

  摘要：

  在本文中，描述了一种由 BiCl 3 /RuCl 3介导的功能化黄酮合成的简便途径，包括：(i)用肉桂酰氯对取代酚进行分子间邻位酰化，以及 (ii)得到邻羟基查耳酮。本文讨论了反应条件。

  DOI：

  10.1039/d1ra00534k

文献信息

• Imafuku, Kimiaki; Honda, Masaaki; McOmie, J. F. W., Synthesis, 1987, # 2, p. 199 - 201
  作者：Imafuku, Kimiaki、Honda, Masaaki、McOmie, J. F. W.

  DOI：——

  日期：——
• Synthesis of 2′,3′,4′-trihydroxyflavone (2-D08), an inhibitor of protein sumoylation
  作者：Yeong Sang Kim、Samantha G.L. Keyser、John S. Schneekloth

  DOI：10.1016/j.bmcl.2014.01.010

  日期：2014.2

  Protein sumoylation is a dynamic posttranslational modification involved in diverse biological processes during cellular homeostasis and development. Recently sumoylation has been shown to play a critical role in cancer, although to date there are few small molecule probes available to inhibit enzymes involved in the SUMO conjugation process. As part of a program to identify and study inhibitors of sumoylation we recently reported the discovery that 2',3',4'-trihydroxyflavone (2-D08) is a cell permeable, mechanistically unique inhibitor of protein sumoylation. The work reported herein describes an efficient synthesis of 2-D08 as well as a structurally related but inactive isomer. We also report an unanticipated Wessely-Moser rearrangement that occurs under vigorous methyl ether deprotection conditions. This rearrangement likely gave rise to 2-D08 during a deprotection step, resulting in 2-D08 appearing as a contaminant in a screening well from a commercial supplier. (C) 2014 Published by Elsevier Ltd.
• IMAFUKU KIMIAKI; HONDA MASAAKI; MCOMIE J. F. W., SYNTHESIS,(1987) N 2, 199-201
  作者：IMAFUKU KIMIAKI、 HONDA MASAAKI、 MCOMIE J. F. W.

  DOI：——

  日期：——
• A novel one-pot synthesis of flavones
  作者：Meng-Yang Chang、Min-Chen Tsai、Chun-Yi Lin

  DOI：10.1039/d1ra00534k

  日期：——

  In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecular ortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resulting o-hydroxychalcones. The reaction conditions are discussed herein.

  在本文中，描述了一种由 BiCl 3 /RuCl 3介导的功能化黄酮合成的简便途径，包括：(i)用肉桂酰氯对取代酚进行分子间邻位酰化，以及 (ii)得到邻羟基查耳酮。本文讨论了反应条件。
• Demethylation-Sulfonation of 2',3',4'-Trimethoxyflavones
  作者：Amar Habsaoui、José Luis Franquet Cami、Emile M. Gaydou、Jean-Claude Wallet

  DOI：10.3987/com-99-8546

  日期：——

  Total demethylation of 2',3',4'-trimethoxyflavones with sulfuric acid was realised at mild temperature giving respective 2',3', 4'-trihydroxyflavone-5'-sulfonic acids. A multi steps mechanism is proposed in the light of earlier results and the complete assignment of the H-1 and C-13 NMR spectra of a suggested 3'-hydroxy-2',4'-dimethoxy intermediate.