(Z)-5-(2-fluoro-2-(3,4,5-trimethoxyphenyl)vinyl)-2-methoxyphenol | 1021917-02-1

• 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)-5-(2-fluoro-2-(3,4,5-trimethoxyphenyl)vinyl)-2-methoxyphenol
• 英文别名: 5-[(Z)-2-fluoro-2-(3,4,5-trimethoxyphenyl)ethenyl]-2-methoxyphenol
• CAS: 1021917-02-1
• 化学式: C₁₈H₁₉FO₅
• 分子量: 334.344
• InChiKey: BSMFLBRBIHSDRE-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：

  C₂₄H₃₃FO₅Si 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 (Z)-5-(2-fluoro-2-(3,4,5-trimethoxyphenyl)vinyl)-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。
• 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 of Bromoundecyl Resorc[4]arenes and Applications of the Cone Stereoisomer as Selector for Liquid Chromatography
  作者：Silvia Corradi、Giulia Mazzoccanti、Francesca Ghirga、Deborah Quaglio、Laura Nevola、Chiara Massera、Franco Ugozzoli、Giuseppe Giannini、Alessia Ciogli、Ilaria D’Acquarica

  DOI：10.1021/acs.joc.8b00488

  日期：2018.8.3

  C-alkylated resorc[4]arenes, we planned to immobilize on a solid support resorc[4]arenes with C11-long side chains in the lower rim. To this purpose, we synthesized two conformationally diverse resorc[4]arenes containing a bromoundecyl moiety in the four axial pendants. The cone stereoisomer 6a (30% yield) was selected for the reaction with an aminopropylated silica gel (APSG) obtained from spherical Kromasil

  作为我们对C-烷基化间苯二酚[4]芳烃多面性质的研究的扩展，我们计划将其固定在下边缘具有C 11-长侧链的固相支持间苯二酚[4]芳烃上。为了这个目的，我们合成了两个构型多样的间苯二[4]芳烃，在四个轴向侧基中含有一个溴氰基部分。选择圆锥立体异构体6a（30％的产率）与从球形Kromasil Si 100、5μm颗粒获得的氨基丙基化硅胶（APSG）反应，得到相应的固定化SP-C 11 -resorc [4]芳烃体系。对生成的极性包埋的固定相进行了充分表征，并在HPLC鉴别E / Z中进行了研究。天然存在的和半合成的康维他汀的立体异构体，康维他汀是（Z）-二苯乙烯抗癌药家族。椅子立体异构体6b（收率20％）在进行X射线衍射分析时显示出在晶格中值得注意的自组装，这是由于分子间Br··O卤素键相互作用而插入的疏水层和极性层的结果，根据独特的堆叠图案。在反相（RP）条件下分离高极性天然产物（即类黄酮
• 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.