5-Fluoro-2-phenoxy-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-2H-chromene | 783342-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 5-Fluoro-2-phenoxy-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-2H-chromene
• CAS: 783342-27-8
• 化学式: C₃₉H₅₅FO₄Si₂
• 分子量: 663.033
• InChiKey: SIUVEYSRPTYMAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.27
• 重原子数：
  46.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Fluoro-2-phenoxy-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-2H-chromene 在 palladium on activated charcoal 偶氮二甲酸二异丙酯 、 硼烷 、 四丁基氟化铵 、 氢气 、 四氯化钛 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 20.0~50.0 ℃ 、101.33 kPa 条件下， 生成 (2R,3R,4S)-5-Fluoro-3-(4-hydroxy-phenyl)-4-methyl-2-{4-[2-((R)-3-methyl-pyrrolidin-1-yl)-ethoxy]-phenyl}-chroman-6-ol
  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：

  5-Fluoro-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-chromen-2-one 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 生成 5-Fluoro-2-phenoxy-6-triisopropylsilanyloxy-3-(4-triisopropylsilanyloxy-phenyl)-2H-chromene
  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