5-iodo-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one | 1185741-05-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 5-iodo-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one
• 英文别名: 5-Iodo-2,2-dimethyl-10-propylpyrano[2,3-f]chromen-8-one
• CAS: 1185741-05-2
• 化学式: C₁₇H₁₇IO₃
• 分子量: 396.225
• InChiKey: HIQODZXQMNRNNN-UHFFFAOYSA-N

物化性质

• 沸点：
  470.3±45.0 °C(predicted)
• 密度：
  1.519±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-硼苯)琥珀酰胺酸 、 5-iodo-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium fluoride 作用下， 以 1,4-二氧六环 为溶剂， 以61%的产率得到4-(4-(2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one-5-yl)phenylamino)-4-oxobutanoic acid
  参考文献：
  名称：

  Synthesis and evaluation of novel substituted 5-hydroxycoumarin and pyranocoumarin derivatives exhibiting significant antiproliferative activity against breast cancer cell lines

  摘要：

  A library of novel 5-hydroxycoumarin and pyranocoumarin derivatives was constructed via silica sulfuric acid-catalyzed pechmann reaction and Pd(0)-catalyzed suzuki coupling in tandem, and their antiproliferative activities against breast cancer cells MCF-7 and MDA-MB-231 were evaluated. The results showed that compounds such as 6b, 6d, 6h, and 6k possess significant antiproliferative activity against MCF-7 cell line with the IC50 values of 7.2, 5.3, 3.3, and 6.5 mu M, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.098
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 、 5-hydroxy-7-iodo-4-propyl-2H-chromen-2-one 在 苯硼酸 作用下， 以 丙酸 、 甲苯 为溶剂， 反应 4.0h， 以81.2%的产率得到5-iodo-2,2-dimethyl-10-propyl-2H,8H-pyrano[2,3-f]chromen-8-one
  参考文献：
  名称：

  Synthesis and evaluation of novel substituted 5-hydroxycoumarin and pyranocoumarin derivatives exhibiting significant antiproliferative activity against breast cancer cell lines

  摘要：

  A library of novel 5-hydroxycoumarin and pyranocoumarin derivatives was constructed via silica sulfuric acid-catalyzed pechmann reaction and Pd(0)-catalyzed suzuki coupling in tandem, and their antiproliferative activities against breast cancer cells MCF-7 and MDA-MB-231 were evaluated. The results showed that compounds such as 6b, 6d, 6h, and 6k possess significant antiproliferative activity against MCF-7 cell line with the IC50 values of 7.2, 5.3, 3.3, and 6.5 mu M, respectively. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.098