5-Fluoro-6-methoxy-3-(4-methoxy-phenyl)-chromen-2-one | 783342-44-9

• 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: 5-Fluoro-6-methoxy-3-(4-methoxy-phenyl)-chromen-2-one
• 英文别名: 5-Fluoro-6-methoxy-3-(4-methoxyphenyl)chromen-2-one
• CAS: 783342-44-9
• 化学式: C₁₇H₁₃FO₄
• 分子量: 300.286
• InChiKey: WSNWWOVSVCPMAV-UHFFFAOYSA-N

物化性质

• 沸点：
  483.7±45.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-Fluoro-6-methoxy-3-(4-methoxy-phenyl)-chromen-2-one 在 palladium on activated charcoal 三氟化硼乙醚 、 硼烷 、 氢气 、 三溴化硼 、 四丁基碘化铵 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 50.0 ℃ 、101.33 kPa 条件下， 生成 4-[(2R,3R,4S)-5-Fluoro-4-methyl-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-chroman-2-yl]-phenol
  参考文献：
  名称：

  Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs

  摘要：

  The discovery, synthesis, and SAR of chromanes as ER alpha subtype selective ligands are described. X-ray studies revealed that the origin of the ER alpha-selectivity resulted from a C-4 trans methyl substitution to the cis-2,3-diphenyl-chromane platform. Selected compounds from this class demonstrated very potent in vivo antagonism of estradiol in an immature rat uterine weight assay, effectively inhibited ovariectomy-induced bone resorption in a 42 days treatment paradigm, and lowered serum cholesterol levels in ovx'd adult rat models. The best antagonists 8F and 12F also exhibited potent inhibition of MCF-7 cell growth and were shown to be estrogen receptor down-regulators (SERDs).

  DOI：

  10.1016/j.bmcl.2005.01.046
• 作为产物：
  描述：

  1,4-二甲氧基-2-氟苯 在 正丁基锂 、 三氯化铝 、 乙酸酐 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 5-Fluoro-6-methoxy-3-(4-methoxy-phenyl)-chromen-2-one
  参考文献：
  名称：

  Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs

  摘要：

  The discovery, synthesis, and SAR of chromanes as ER alpha subtype selective ligands are described. X-ray studies revealed that the origin of the ER alpha-selectivity resulted from a C-4 trans methyl substitution to the cis-2,3-diphenyl-chromane platform. Selected compounds from this class demonstrated very potent in vivo antagonism of estradiol in an immature rat uterine weight assay, effectively inhibited ovariectomy-induced bone resorption in a 42 days treatment paradigm, and lowered serum cholesterol levels in ovx'd adult rat models. The best antagonists 8F and 12F also exhibited potent inhibition of MCF-7 cell growth and were shown to be estrogen receptor down-regulators (SERDs).

  DOI：

  10.1016/j.bmcl.2005.01.046