(2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5,6-trimethoxy-1-benzofuran-3-one | 527750-40-9

• 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: (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5,6-trimethoxy-1-benzofuran-3-one
• CAS: 527750-40-9
• 化学式: C₁₉H₁₈O₇
• 分子量: 358.348
• InChiKey: CEWHDEVAWUZGKB-ZSOIEALJSA-N

物化性质

• 沸点：
  597.8±50.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 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：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5,6-trimethoxy-1-benzofuran-3-one 在 potassium cyanide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 12.0h， 以20%的产率得到半齿泽兰素-5-甲醚
  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 (2Z)-2-[(3-hydroxy-4-methoxyphenyl)methylidene]-4,5,6-trimethoxy-1-benzofuran-3-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

• 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.