2,2,2-三氯-1-(2-氟-4-甲氧基苯基)乙醇 | 1403674-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,2,2-三氯-1-(2-氟-4-甲氧基苯基)乙醇
• 英文名称: 2,2,2-trichloro-1-(2-fluoro-4-methoxyphenyl)ethanol
• CAS: 1403674-64-5
• 化学式: C₉H₈Cl₃FO₂
• 分子量: 273.519
• InChiKey: YGKSHZDYHGVXJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,2-三氯-1-(2-氟-4-甲氧基苯基)乙醇 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 氯化亚砜 、 乙醇 、 二苯基二硒醚 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 1,2-bis(2-fluoro-4-methoxyphenyl)-ethane-1-one
  参考文献：
  名称：

  Influence of Chlorine or Fluorine Substitution on the Estrogenic Properties of 1-Alkyl-2,3,5-tris(4-hydroxyphenyl)-1H-pyrroles

  摘要：

  In continuation of Our previous work, several 1- alkyl-2,3,5-tris(4-hydroxyphenyl)aryl-1H-pyrroles with chlor-Me or fluorine substituents in the aryl residues were synthesized and tested for estrogen receptor (ER) binding at isolated ER alpha/ER beta. receptors (HAP assay), and. in trans activation assays using ER alpha-positive MCF-7/2a as well as U2-OS/ER alpha and U2-OS/ER beta cells. In the competition experiment at ER alpha the compounds displayed very high relative binding-affinities of up to 37% (determined for 8m) but with restricted subtype selectivity (e.g., ER alpha/ER beta (8ma) = 9). The highest estrogenic potency in ER alpha-positive MCP-7/2a cells was determined for 2,3,5-tris(2-fluoro-4-hydroxyphenyl)-1-prolayl-1H-pyriole 8m (EC50 = 23 nM), while in U2-OS/ER alpha cells 2-(2-fluoro-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)-1H propyl-1H pyrrole 8b (EC50 = 0.12 nM) was the Most potent agonist, only 30 fold less active than estradiol (E2, EC50 = 0.004 nM). In U2-OS/ER beta cells for all pyrroles no transactivation could be observed, which indicates that they are selective ER alpha agonists in Cellular systems.

  DOI：

  10.1021/jm300860j
• 作为产物：
  描述：

  氯仿 、 2-氟-4-甲氧基苯甲醛 在 potassium hydroxide 、 盐酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 0.5h， 以97%的产率得到2,2,2-三氯-1-(2-氟-4-甲氧基苯基)乙醇
  参考文献：
  名称：

  Influence of Chlorine or Fluorine Substitution on the Estrogenic Properties of 1-Alkyl-2,3,5-tris(4-hydroxyphenyl)-1H-pyrroles

  摘要：

  In continuation of Our previous work, several 1- alkyl-2,3,5-tris(4-hydroxyphenyl)aryl-1H-pyrroles with chlor-Me or fluorine substituents in the aryl residues were synthesized and tested for estrogen receptor (ER) binding at isolated ER alpha/ER beta. receptors (HAP assay), and. in trans activation assays using ER alpha-positive MCF-7/2a as well as U2-OS/ER alpha and U2-OS/ER beta cells. In the competition experiment at ER alpha the compounds displayed very high relative binding-affinities of up to 37% (determined for 8m) but with restricted subtype selectivity (e.g., ER alpha/ER beta (8ma) = 9). The highest estrogenic potency in ER alpha-positive MCP-7/2a cells was determined for 2,3,5-tris(2-fluoro-4-hydroxyphenyl)-1-prolayl-1H-pyriole 8m (EC50 = 23 nM), while in U2-OS/ER alpha cells 2-(2-fluoro-4-hydroxyphenyl)-3,5-bis(4-hydroxyphenyl)-1H propyl-1H pyrrole 8b (EC50 = 0.12 nM) was the Most potent agonist, only 30 fold less active than estradiol (E2, EC50 = 0.004 nM). In U2-OS/ER beta cells for all pyrroles no transactivation could be observed, which indicates that they are selective ER alpha agonists in Cellular systems.

  DOI：

  10.1021/jm300860j