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

文献信息

• Estrogen receptor ligands. Part 10: Chromanes: old scaffolds for new SERAMs
  作者：Qiang Tan、Timothy A. Blizzard、Jerry D. Morgan、Elizabeth T. Birzin、Wanda Chan、Yi Tien Yang、Lee-Yuh Pai、Edward C. Hayes、Carolyn A. DaSilva、Sudha Warrier、Joel Yudkovitz、Hilary A. Wilkinson、Nandini Sharma、Paula M.D. Fitzgerald、Susan Li、Lawrence Colwell、John E. Fisher、Sharon Adamski、Alfred A. Reszka、Donald Kimmel、Frank DiNinno、Susan P. Rohrer、Leonard P. Freedman、James M. Schaeffer、Milton L. Hammond

  DOI：10.1016/j.bmcl.2005.01.046

  日期：2005.3

  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).