5-[(E)-2-bromo-2-fluoro-vinyl]-2-methoxy-phenol | 1021916-43-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-[(E)-2-bromo-2-fluoro-vinyl]-2-methoxy-phenol
• CAS: 1021916-43-7
• 化学式: C₉H₈BrFO₂
• 分子量: 247.064
• InChiKey: ARCIOKPJJLAHGH-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.06
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  异香兰素 、 氟三溴甲烷 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-[(Z)-2-bromo-2-fluoro-vinyl]-2-methoxy-phenol 、 5-[(E)-2-bromo-2-fluoro-vinyl]-2-methoxy-phenol
  参考文献：
  名称：

  Synthesis and Biological Activity of Fluorinated Combretastatin Analogues

  摘要：

  With the aim of understanding the influence of fluorine on the double bond of the cis-stilbene moiety of combretastatin derivatives and encouraged by a preliminary molecular modeling study showing a different biological environment on the interaction site with tubulin, we prepared, through various synthetic approaches, a small library of compounds in which one or both of the olefinic hydrogens were replaced with fluorine. X-ray analysis on the difluoro-CA-4 analogue demonstrated that the spatial arrangement of the molecule was not modified, compared to its nonfluorinated counterpart. SAR analysis confirmed the importance of the cis-stereochemistry of the stilbene scaffold. Nevertheless, some unpredicted results were observed on a few trans-fluorinated derivatives. The position of a fluorine atom on the double bond may affect the inhibition of tubulin polymerization and cytotoxic activity of these compounds.

  DOI：

  10.1021/jm701362m