7-(allyloxy)-3-(benzo[d][1,3]dioxol-5-yl)-5-hydroxy-4H-chromen-4-one | 1005417-98-0

• 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: 7-(allyloxy)-3-(benzo[d][1,3]dioxol-5-yl)-5-hydroxy-4H-chromen-4-one
• 英文别名: 3-(1,3-Benzodioxol-5-yl)-5-hydroxy-7-prop-2-enoxychromen-4-one
• CAS: 1005417-98-0
• 化学式: C₁₉H₁₄O₆
• 分子量: 338.317
• InChiKey: CEAMINIVHTYLJO-UHFFFAOYSA-N

物化性质

• 沸点：
  565.5±50.0 °C(Predicted)
• 密度：
  1.403±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  7-(allyloxy)-3-(benzo[d][1,3]dioxol-5-yl)-5-hydroxy-4H-chromen-4-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 8-allyl-3-(benzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 、 6-allyl-3-(benzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Derrubone and Select Analogues

  摘要：

  [GRAPHICS]Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.

  DOI：

  10.1021/jo702366g
• 作为产物：
  描述：

  3-(benzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 、 3-溴丙烯 在 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以85%的产率得到7-(allyloxy)-3-(benzo[d][1,3]dioxol-5-yl)-5-hydroxy-4H-chromen-4-one
  参考文献：
  名称：

  Synthesis and Evaluation of Derrubone and Select Analogues

  摘要：

  [GRAPHICS]Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.

  DOI：

  10.1021/jo702366g

文献信息

• Synthesis and Evaluation of Derrubone and Select Analogues
  作者：Jedidiah M. Hastings、M. Kyle Hadden、Brian S. J. Blagg

  DOI：10.1021/jo702366g

  日期：2008.1.1

  [GRAPHICS]Recently, we reported that the natural product derrubone exhibits Hsp90 inhibitory activity. Due to its unique architectural scaffold and proposed rapid assembly, the synthesis of this natural product was pursued with the aim of identifying structure-activity relationships. Synthesis of the natural product was accomplished in eight highly convergent steps, which led to a facile method for the construction of related compounds. Biological evaluation of derrubone and its analogues identified several compounds that exhibit low micromolar inhibitory activity against breast and colon cancer cell lines.