1-(4-aminophenyl)-1-<4-<2-(N,N-dimethylamino)ethoxy>phenyl>-2-phenyl-1-butene | 97732-67-7

• 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-aminophenyl)-1-<4-<2-(N,N-dimethylamino)ethoxy>phenyl>-2-phenyl-1-butene
• 英文别名: 3-[1-[4-[2-(dimethylamino)ethoxy]phenyl]-2-phenylbut-1-enyl]aniline
• CAS: 97732-67-7
• 化学式: C₂₆H₃₀N₂O
• 分子量: 386.537
• InChiKey: NWEZKIZRFWLHSM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  38.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  哌啶 、 1-(4-aminophenyl)-1-<4-<2-(N,N-dimethylamino)ethoxy>phenyl>-2-phenyl-1-butene 在 盐酸 、 sodium nitrite 作用下， 生成 (E)-1-<4-(piperidinoazo)phenyl>-1-<4-<2-(N,N-dimethylamino)ethoxy>phenyl>-2-phenyl-1-butene 、 (Z)-1-<4-(piperidinoazo)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