2-氟-6-羟基-3-甲氧基苯甲醛 | 783342-35-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-氟-6-羟基-3-甲氧基苯甲醛
• 英文名称: 2-Fluoro-6-hydroxy-3-methoxybenzaldehyde
• CAS: 783342-35-8
• 化学式: C₈H₇FO₃
• mdl: MFCD11520915
• 分子量: 170.14
• InChiKey: YKRNNPSJAWJHRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  2-氟-6-羟基-3-甲氧基苯甲醛 在 palladium on activated charcoal 三氟化硼乙醚 、 硼烷 、 氢气 、 乙酸酐 、 三溴化硼 、 四丁基碘化铵 、 二异丁基氢化铝 、 三乙胺 、 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， 145.0 ℃ 、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：

  2-氟-3,6-二甲氧基苯甲醛 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到2-氟-6-羟基-3-甲氧基苯甲醛
  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