(E)-4-(1-(4-(2-(ethoxycarbonyl(methyl)amino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenyl pivalate | 1231732-30-1

• 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: (E)-4-(1-(4-(2-(ethoxycarbonyl(methyl)amino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenyl pivalate
• CAS: 1231732-30-1
• 化学式: C₃₃H₃₉NO₅
• 分子量: 529.676
• InChiKey: LUWBGOFEEZTGNW-FLWNBWAVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.47
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  ethyl 2-iodoethyl(methyl)carbamate 、 (E)-4-(1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl)phenyl pivalate 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (E)-4-(1-(4-(2-(ethoxycarbonyl(methyl)amino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenyl pivalate 、 (E)-4-(1-(4-(2-(ethoxycarbonyl(methyl)amino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenyl pivalate
  参考文献：
  名称：

  A convenient synthesis of (Z)-4-hydroxy-N-desmethyltamoxifen (endoxifen)

  摘要：

  A mixture of the (Z)- and (E)-isomers of 4-hydroxy-N-desmethyltamoxifen was conveniently prepared in four steps. These geometrical isomers were then neatly separated by semi-preparative Reverse Phase High Performance Liquid Chromatography (RP-HPLC) using specified conditions. Additionally, the isolated E-isomer could be equilibrated in aqueous strong acid in acetonitrile or trifluoroacetic acid/dichloromethane to give a clean 1: 1 mixture of Z/E isomers that was re-subjected to HPLC separation. In this way, most of the undesired (E)-isomer could be readily converted to the desired (Z)-isomer providing quick access to over 200 mg quantities of pure endoxifen (Z-isomer), a potent antiestrogenic metabolite of tamoxifen traditionally used in breast cancer treatment. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.03.117