(Z)-4,5,6-trimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one | 95937-57-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 橙酮类黄酮
• 英文名称: (Z)-4,5,6-trimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one
• 英文别名: 4,5,6-trimethoxy-2-((Z)-4-methoxy-benzylidene)-benzofuran-3-one；4,5,6-Trimethoxy-2-((Z)-4-methoxy-benzyliden)-benzofuran-3-on；4,5,6-Trimethoxy-3-oxo-2-<4-methoxy-benzyliden>-2,3-dihydro-benzofuran；4.5.6.4'-Tetramethoxy-auron；4,5,6-Trimethoxy-3-oxo-2-(4-methoxy-benzyliden)-2,3-dihydro-benzofuran；(2Z)-4,5,6-trimethoxy-2-[(4-methoxyphenyl)methylidene]-1-benzofuran-3-one
• CAS: 95937-57-8
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: USMNURMDIJSEAI-ZROIWOOFSA-N

物化性质

• 熔点：
  148-149 °C
• 沸点：
  545.6±50.0 °C(Predicted)
• 密度：
  1.268±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-4,5,6-trimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one 在 potassium cyanide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以73%的产率得到4’,5,6,7-四甲氧基黄酮
  参考文献：
  名称：

  The total synthesis of an aurone isolated from Uvaria hamiltonii : aurones and flavones as anticancer agents

  摘要：

  The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G(2)/M cell-cycle arrest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.003
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 aluminum oxide 、 PPA 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 (Z)-4,5,6-trimethoxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one
  参考文献：
  名称：

  The total synthesis of an aurone isolated from Uvaria hamiltonii : aurones and flavones as anticancer agents

  摘要：

  The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G(2)/M cell-cycle arrest. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.07.003

文献信息

• Oxidation of chalcones (AFO reaction)
  作者：B. Cummins、D.M.X. Donnelly、J.F. Eades、H. Fletcher、F.O' Cinnéide、E.M. Philbin、J. Swirski、T.S. Wheeler、R.K. Wilson

  DOI：10.1016/s0040-4020(01)98539-4

  日期：1963.1

  Discrepancies in published work on the alkaline peroxide oxidation of chalcones (AFO reaction) have been examined. It has been found that in addition to flavonols and aurones, 2-benzyl-2-hydroxydihydrobenzofuran-3-ones (IX), and 2-arylbenzofuran-3-carboxylic acids (XV), each new as regards this reaction, appear in the products. A mechanism for the production of these latter compounds is suggested.

  已经检查了有关查尔酮的碱性过氧化物氧化（AFO反应）的已发表工作中的差异。已经发现，除了黄酮醇和金酮之外，在该反应中还出现了2-苄基-2-羟基二氢苯并呋喃-3-酮（IX）和2-芳基苯并呋喃-3-羧酸（XV）。产品。建议了产生这些后面的化合物的机理。
• Divergent Approach to Flavones and Aurones via Dihaloacrylic Acids. Unexpected Dependence on the Halogen Atom
  作者：George A. Kraus、Vinayak Gupta

  DOI：10.1021/ol1023294

  日期：2010.11.19

  The reaction of phenols with 7a led to the synthesis of aurones, while the reaction of phenols with 7b led to the synthesis of flavones.
• Derivatives of Coumaran. IV. The Structure of Tectorigenin
  作者：R. L. Shriner、Edward J. Matson、R. E. Damschroder

  DOI：10.1021/ja01878a017

  日期：1939.9
• Philbin et al., Chemistry and Industry, 1956, p. 1018
  作者：Philbin et al.

  DOI：——

  日期：——
• The total synthesis of an aurone isolated from Uvaria hamiltonii : aurones and flavones as anticancer agents
  作者：Nicholas J. Lawrence、David Rennison、Alan T. McGown、John A. Hadfield

  DOI：10.1016/j.bmcl.2003.07.003

  日期：2003.11

  The naturally occurring aurone 1, isolated from Uvaria hamiltonii, and a series of aurones analogues based structurally on known tubulin binding agents were prepared and evaluated for anticancer activity. Aurone 20 was the most active (IC50 K562 50 nM) and caused significant G(2)/M cell-cycle arrest. (C) 2003 Elsevier Ltd. All rights reserved.