(Z)-2-(4-(1-bromo-2-fluoro-2-phenylvinyl)phenoxy)ethanol | 1418146-30-1

• 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: (Z)-2-(4-(1-bromo-2-fluoro-2-phenylvinyl)phenoxy)ethanol
• 英文别名: 2-[4-[(Z)-1-bromo-2-fluoro-2-phenylethenyl]phenoxy]ethanol
• CAS: 1418146-30-1
• 化学式: C₁₆H₁₄BrFO₂
• 分子量: 337.188
• InChiKey: XBYLJEQUWVJWEH-NXVVXOECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  Tert-butyl-[2-[4-(2,2-difluoro-1-iodoethenyl)phenoxy]ethoxy]-dimethylsilane 在 正丁基锂 、 sodium methylate 、 tetra-N-butylammonium tribromide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (Z)-2-(4-(1-bromo-2-fluoro-2-phenylvinyl)phenoxy)ethanol 、 (E)-2-(4-(1-bromo-2-fluoro-2-phenylvinyl)phenoxy)ethanol
  参考文献：
  名称：

  Synthesis and growth inhibition activity of fluorinated derivatives of tamoxifen

  摘要：

  The design and synthesis of 11 fluorinated derivatives of tamoxifen are described. Growth inhibition values (GI(50)) on human HT-29, M21, MCF7, and MDA-MB-231 tumor cells are also reported. In general, the GI(50) values are similar or slightly higher than tamoxifen with the most active compound on MCF7 cell line having a GI(50) = 3.6 mu M. Surprisingly, as opposed to tamoxifen, both geometrical isomers behave similarly. We hypothesize that this behavior is due to in vitro isomerization of the compounds. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.01.057

文献信息

• Bromination/desilicobromination of silylated monofluoroalkenes using tetrabutylammonium tribromide under microwave conditions
  作者：Bianca Malo-Forest、Jessye-Ann Roy、Jean-François Paquin

  DOI：10.1016/j.jfluchem.2012.10.008

  日期：2013.1

  tetrabutylammonium tribromide under microwave conditions are presented. The reaction is fast (20 min) and provide, after the desilicobromination step, the bromofluoroalkene where the replacement of the silyl group is done with retention of configuration with little or no stereochemical erosion. Isomeric enrichment is even observed in one case. Optimization of the reactions conditions and applications to various substrates

  提出了在微波条件下使用四丁基三溴化铵溴化/去甲硅烷基化单氟烯烃的新条件。反应快速（20分钟），并在脱硅溴化步骤之后提供了溴氟烯烃，其中的甲硅烷基取代是在保留构型的情况下进行的，几乎不发生或不发生立体化学腐蚀。在一种情况下甚至观察到异构富集。报道了反应条件的优化和在各种底物上的应用。