5-[(E)-2-fluoro-2-(3,4,5-trimethoxyphenyl)ethenyl]-2-methoxyphenol | 824976-22-9

• 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: 5-[(E)-2-fluoro-2-(3,4,5-trimethoxyphenyl)ethenyl]-2-methoxyphenol
• CAS: 824976-22-9
• 化学式: C₁₈H₁₉FO₅
• 分子量: 334.344
• InChiKey: BSMFLBRBIHSDRE-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到5-[(E)-2-fluoro-2-(3,4,5-trimethoxyphenyl)ethenyl]-2-methoxyphenol
  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

文献信息

• 一种制备高选择性单氟烯烃的试剂
  申请人：中国科学院上海有机化学研究所

  公开号：CN104447521B

  公开（公告）日：2021-09-03

  本发明提供了一种制备高选择性单氟烯烃的试剂，具体地，本发明提供了一种能够高选择性地制备单氟烯烃的试剂，及使用所述试剂制备单氟烯烃的方法。本发明的方法条件温和，转化率高，可以任选地用于制备高度构型纯的Z式或E式烯烃，成本低，适合用于大规模生产。
• Spontaneous Resolution of Julia-Kocienski Intermediates Facilitates Phase Separation to Produce <i>Z</i>- and <i>E</i>-Monofluoroalkenes
  作者：Yanchuan Zhao、Fanzhou Jiang、Jinbo Hu

  DOI：10.1021/jacs.5b02112

  日期：2015.4.22

  The monofluoroalkene motif is important in drug development as it serves as a peptide bond isostere and is found in a number of biologically active compounds with various pharmacological activities. Direct olefination of carbonyl compound is a straightforward way to prepare monofluoroalkenes; however, these methods often result in a mixture of Z- and E-isomers that cannot be easily separated. We discovered a unique spontaneous resolving reaction that simultaneously addresses the problems in the synthesis and separation of Z- and E-monofluoroalkenes. The reaction is accompanied by a highly efficient spontaneous kinetic resolution and phase labeling of monofluoroalkene precursors which allows the separation of Z- and E-monofluoroalkenes by liquid-liquid extraction. The application of the method is demonstrated by the synthesis and separation of potential anticancer agents, which are inseparable by HPLC.
• Synthesis and Biological Activity of Fluorinated Combretastatin Analogues
  作者：Domenico Alloatti、Giuseppe Giannini、Walter Cabri、Isabella Lustrati、Mauro Marzi、Andrea Ciacci、Grazia Gallo、M. Ornella Tinti、Marcella Marcellini、Teresa Riccioni、Mario B. Guglielmi、Paolo Carminati、Claudio Pisano

  DOI：10.1021/jm701362m

  日期：2008.5.1

  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.