1-<4-(acetylamino)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene | 97732-65-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-<4-(acetylamino)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene
• CAS: 97732-65-5
• 化学式: C₂₄H₂₃NO₂
• 分子量: 357.452
• InChiKey: YUZBTGFWYLWGOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  27.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.33
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  二甲氨基氯乙烷盐酸 、 1-<4-(acetylamino)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 (Z)-1-<4-(acetylamino)phenyl>-1-<4-<2-(N,N-dimethylamino)ethoxy>phenyl>-2-phenyl-1-butene 、 (E)-1-<4-(acetylamino)phenyl>-1-<4-<2-(N,N-dimethylamino)ethoxy>phenyl>-2-phenyl-1-butene
  参考文献：
  名称：

  Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent

  摘要：

  Aminotamoxifen was totally synthesized from p-nitrobenzoyl chloride via a Friedel-Crafts acylation. Then, by means of a Balz-Schiemann reaction, aminotamoxifen was converted into fluorotamoxifen. The triazene variation of this conversion, with a 25% yield, enables a rapid, one-step diazotization, incorporating a fluorine atom into the phenyl ring of the tamoxifen. This reaction may be useful for the preparation of low specific activity 18F-labeled tamoxifen, for distribution, and for estrogen-receptor studies. For these in vivo and in vitro studies, fluorotamoxifen was also synthesized from p-fluorobenzoyl chloride, and its chemical intermediates were compared with estradiol and hexestrol, for their receptor binding and competition, as well as for their uterotropic activity. It is demonstrated that tamoxifen and fluorotamoxifen are strong estradiol agonists and partial hexestrol agonists, while aminotamoxifen is a weak estradiol and hexestrol agonist.

  DOI：

  10.1021/jm00148a022
• 作为产物：
  描述：

  1-<4-(acetylamino)phenyl>-1-(4-methoxyphenyl)-2-phenyl-1-butene 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以54%的产率得到1-<4-(acetylamino)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene
  参考文献：
  名称：

  Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent

  摘要：

  Aminotamoxifen was totally synthesized from p-nitrobenzoyl chloride via a Friedel-Crafts acylation. Then, by means of a Balz-Schiemann reaction, aminotamoxifen was converted into fluorotamoxifen. The triazene variation of this conversion, with a 25% yield, enables a rapid, one-step diazotization, incorporating a fluorine atom into the phenyl ring of the tamoxifen. This reaction may be useful for the preparation of low specific activity 18F-labeled tamoxifen, for distribution, and for estrogen-receptor studies. For these in vivo and in vitro studies, fluorotamoxifen was also synthesized from p-fluorobenzoyl chloride, and its chemical intermediates were compared with estradiol and hexestrol, for their receptor binding and competition, as well as for their uterotropic activity. It is demonstrated that tamoxifen and fluorotamoxifen are strong estradiol agonists and partial hexestrol agonists, while aminotamoxifen is a weak estradiol and hexestrol agonist.

  DOI：

  10.1021/jm00148a022