5-[(Z)-1-fluoro-2-(3,4,5-trimethoxyphenyl)ethenyl]-2-methoxyphenol | 1021916-82-4

• 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-[(Z)-1-fluoro-2-(3,4,5-trimethoxyphenyl)ethenyl]-2-methoxyphenol
• CAS: 1021916-82-4
• 化学式: C₁₈H₁₉FO₅
• 分子量: 334.344
• InChiKey: MERONNUGBUIKIW-QPEQYQDCSA-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：

  tert-butyl-{5-[(Z)-1-fluoro-2-(3,4,5-trimethoxy-phenyl)-vinyl]-2-methoxy-phenoxy}-dimethyl-silane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 5-[(Z)-1-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

• Hydrofluorination of Alkynes Catalysed by Gold Bifluorides
  作者：Fady Nahra、Scott R. Patrick、Davide Bello、Marcel Brill、Alan Obled、David B. Cordes、Alexandra M. Z. Slawin、David O'Hagan、Steven P. Nolan

  DOI：10.1002/cctc.201402891

  日期：2015.1

  N‐heterocyclic carbene gold bifluoride complexes starting from the corresponding N‐heterocyclic carbene gold hydroxides. A new methodology to access N,N′‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene gold(I) fluoride starting from N,N′‐bis(2,6‐diisopropylphenyl)imidazol‐2‐ylidene gold(I) hydroxide and readily available potassium bifluoride is also reported. These gold bifluorides were shown to be efficient

  我们报道了以相应的N-杂环卡宾金氢氧化物为原料合成了九种新的N-杂环卡宾金二氟化物络合物。一种以N,N'-双(2,6-二异丙基苯基)咪唑-2-亚基金(I)为原料制备N,N'-双(2,6-二异丙基苯基)咪唑-2-亚基金(I)氟化物的新方法( I) 氢氧化物和容易获得的氟化氢钾也有报道。这些二氟化金被证明是对称和不对称炔烃氢氟化的有效催化剂，从而以良好至优异的产率提供氟化二苯乙烯类似物和氟乙烯基硫醚，并具有高立体和区域选择性。该方法进一步用于从市售试剂开始分两步选择性地获得氟化考布他汀类似物。
• 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.