6-fluoro-3-hydroxy-4-methoxystyrene | 1335242-21-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-fluoro-3-hydroxy-4-methoxystyrene
• 英文别名: 5-Ethenyl-4-fluoro-2-methoxyphenol；5-ethenyl-4-fluoro-2-methoxyphenol
• CAS: 1335242-21-1
• 化学式: C₉H₉FO₂
• 分子量: 168.168
• InChiKey: UPOGFFRKUFTQMI-UHFFFAOYSA-N

物化性质

• 沸点：
  273.8±40.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-fluoro-3-hydroxy-4-methoxystyrene 、 5-碘邻苯二酚 在 三乙醇胺 、 palladium diacetate 作用下， 反应 24.0h， 以81.2%的产率得到(E)-1-(3,5-dihydroxyphenyl)-2-(2'-fluoro-5'-hydroxy-4'-methoxyphenyl)ethene
  参考文献：
  名称：

  白藜芦醇衍生的丁酰胆碱酯酶抑制剂

  摘要：

  通过 Mizoroki-Heck 反应合成了新型多羟基化 (E)-二苯乙烯，并测试了它们抑制乙酰胆碱酯酶和丁酰胆碱酯酶的能力。其中一些是丁酰胆碱酯酶的良好抑制剂；其中一种带有额外氟取代基的丁酰胆碱酯酶抑制剂是乙酰胆碱酯酶抑制剂的 94 倍。

  DOI：

  10.1002/ardp.201300051
• 作为产物：
  描述：

  甲基三苯基碘化膦 、 2-fluoro-5-hydroxy-4-methoxybenzaldehyde 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 生成 6-fluoro-3-hydroxy-4-methoxystyrene
  参考文献：
  名称：

  白藜芦醇衍生的丁酰胆碱酯酶抑制剂

  摘要：

  通过 Mizoroki-Heck 反应合成了新型多羟基化 (E)-二苯乙烯，并测试了它们抑制乙酰胆碱酯酶和丁酰胆碱酯酶的能力。其中一些是丁酰胆碱酯酶的良好抑制剂；其中一种带有额外氟取代基的丁酰胆碱酯酶抑制剂是乙酰胆碱酯酶抑制剂的 94 倍。

  DOI：

  10.1002/ardp.201300051

文献信息

• Synthesis and Radical Scavenging Activities of Resveratrol Analogs
  作者：René Csuk、Sabrina Albert、Bianka Siewert

  DOI：10.1002/ardp.201300081

  日期：2013.7

  polyhydroxylated (E)‐stilbenes were synthesized by Mizoroki–Heck reactions and tested for their ability to act as radical scavenger. One of the 56 stilbenes included in this study and investigated in DPPH assays gave an SC50 value of 11.0 μM, hence exhibiting an about 9.3 times higher activity than resveratrol. As shown in a photometric SRB assay using mouse NiH 3T3 fibroblasts, this compound is not cytotoxic up

  通过 Mizoroki-Heck 反应合成了高度取代的多羟基化 (E)-二苯乙烯，并测试了它们作为自由基清除剂的能力。本研究中包括并在 DPPH 测定中研究的 56 种芪中之一的 SC50 值为 11.0 μM，因此其活性比白藜芦醇高约 9.3 倍。如使用小鼠 NiH 3T3 成纤维细胞的光度 SRB 测定所示，该化合物在浓度小于 30 μM 时没有细胞毒性。
• Synthesis and antimicrobial activity of (E) stilbene derivatives
  作者：Sabrina Albert、Ralf Horbach、Holger B. Deising、Bianka Siewert、René Csuk

  DOI：10.1016/j.bmc.2011.07.015

  日期：2011.9

  Plants use multiple defence mechanisms comprising both constitutive and inducible barriers to prevent entering of phytopathogenic micro-organisms. In many plant species one of the most efficient responses to combat attacking microbes is the rapid synthesis of antimicrobial low molecular weight phytoalexins, for example, resveratrol, 3,5,4'-trihydroxystilbene (1). Resveratrol and its natural derivatives, however, display only moderate antimicrobial effects. Nevertheless, resveratrol may be a useful lead structure for the chemical synthesis of antimicrobials. In this study, several series of stilbenes have been synthesized, starting from the aldehydes using Wittig reactions to access the corresponding styrenes that were subjected to Mizoroki-Heck reactions to yield the stilbenes in good yields. The stilbenes were tested in an agar diffusion assay against several bacteria and fungi. For some of these compounds the inhibiting zones for bacteria and fungi were comparable with those of the antibiotics tetracycline, streptomycin, ampicillin, or kanamycin, directed against prokaryotes, and nourseothricin or hygromycin controlling fungi, respectively. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of novel (E) stilbene-based antitumor agents
  作者：René Csuk、Sabrina Albert、Bianka Siewert、Stefan Schwarz

  DOI：10.1016/j.ejmech.2012.06.015

  日期：2012.8

  Several new (E) stilbenes were synthesized by a combination of a Wittig olefination followed by Mizoroki-Heck coupling reactions. These compounds were screened for antitumor activity in a panel of 8 human cancer cell lines by a colorimetric SRB assay. Several of these compounds exhibit strong cytotoxicity. The most active compound of this series showed an average IC50 value of 0.03 mu mol; it acts by apoptosis as shown by a dye-exclusion test, an extra acridine orange/ethidium bromide staining and DNA-laddering experiments. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Resveratrol Derived Butyrylcholinesterase Inhibitors
  作者：René Csuk、Sabrina Albert、Ralph Kluge、Dieter Ströhl

  DOI：10.1002/ardp.201300051

  日期：2013.7

  (E)‐stilbenes were synthesized by Mizoroki–Heck reactions and tested for their ability to inhibit the enzymes acetyl‐ and butyrylcholinesterase. Several of them are good inhibitors of butyrylcholinesterase; one of them carrying an extra fluorine substituent is a 94‐fold stronger inhibitor of butyrylcholinesterase than of acetylcholinesterase.

  通过 Mizoroki-Heck 反应合成了新型多羟基化 (E)-二苯乙烯，并测试了它们抑制乙酰胆碱酯酶和丁酰胆碱酯酶的能力。其中一些是丁酰胆碱酯酶的良好抑制剂；其中一种带有额外氟取代基的丁酰胆碱酯酶抑制剂是乙酰胆碱酯酶抑制剂的 94 倍。