5-溴-2-氟苯-1,3-二醇 | 570391-16-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 5-溴-2-氟苯-1,3-二醇
• 中文别名: 5-溴-2-氟间苯二酚
• 英文名称: 3,5-dihydroxy-4-fluoro-bromobenzene
• 英文别名: 4-fluoro-3,5-dihydroxybromobenzene；2-fluoro-5-bromobenzene-1,3-diol；5-bromo-2-fluorobenzene-1,3-diol；5-bromo-2-fluororesorcinol
• CAS: 570391-16-1
• 化学式: C₆H₄BrFO₂
• 分子量: 206.999
• InChiKey: CQXAFELRNPEOTP-UHFFFAOYSA-N

物化性质

• 熔点：
  83-86 °C(Solv: dichloromethane (75-09-2))
• 沸点：
  267.5±35.0 °C(Predicted)
• 密度：
  1.940±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,4-二甲氧基苯乙烯 、 5-溴-2-氟苯-1,3-二醇 在 三乙醇胺 、 palladium diacetate 作用下， 反应 24.0h， 以63.7%的产率得到(E)-3',5'-dihydroxy-3,4-dimethoxy-4'-fluorostilbene
  参考文献：
  名称：

  白藜芦醇类似物的合成和自由基清除活性

  摘要：

  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。

  DOI：

  10.1002/ardp.201300081
• 作为产物：
  描述：

  5-溴-2-氟-1,3-亚苯基二硼酸频那醇酯 在 Oxone 作用下， 以 水 、 丙酮 为溶剂， 反应 0.6h， 以66%的产率得到5-溴-2-氟苯-1,3-二醇
  参考文献：
  名称：

  [EN] COMPOSITIONS FOR THE TREATMENT OF HYPERTENSION AND/OR FIBROSIS
  [FR] COMPOSITIONS POUR LE TRAITEMENT DE L'HYPERTENSION ET/OU DE LA FIBROSE

  摘要：

  本发明涉及新化合物及其在预防性和/或治疗高血压和/或纤维化的用途。

  公开号：

  WO2015039172A1

文献信息

• 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。
• Process for the synthesis of phenols from arenes
  申请人：Board of Trustees of Michigan State University

  公开号：US20040030197A1

  公开（公告）日：2004-02-12

  A process to synthesize substituted phenols such as those of the general formula RR′R″Ar(OH) wherein R, R′, and R″ are each independently hydrogen or any group which does not interfere in the process for synthesizing the substituted phenol including, but not limited to, halo, alkyl, alkoxy, carboxylic ester, amine, amide; and Ar is any variety of aryl or hetroaryl by means of oxidation of substituted arylboronic esters is described. In particular, a metal-catalyzed C—H activation/borylation reaction is described, which when followed by direct oxidation in a single or separate reaction vessel affords phenols without the need for any intermediate manipulations. More particularly, a process wherein Ir-catalyzed borylation of arenes using pinacolborane (HBPin) followed by oxidation of the intermediate arylboronic ester by OXONE is described.

  描述了一种合成取代酚的过程，如通式RR′R″Ar(OH)中的那些，其中R、R′和R″分别独立地是氢或不干扰合成取代酚过程的任何基团，包括但不限于卤素、烷基、烷氧基、羧酸酯、胺、酰胺；Ar是芳基或杂芳基的任何种类，通过氧化取代芳基硼酸酯来实现。具体地，描述了一种金属催化的C—H活化/硼化反应，随后在单个或分离的反应容器中直接氧化，从而获得酚，无需任何中间操作。更具体地，描述了一种通过Ir催化的芳烃硼化反应，使用二醇硼烷（HBPin）后，通过OXONE氧化中间芳基硼酸酯的过程。
• 空穴传输材料及其制备方法、有机发光器件
  申请人：武汉华星光电半导体显示技术有限公司

  公开号：CN110669059A

  公开（公告）日：2020-01-10

  本发明公开了一种空穴传输材料及其制备方法、有机发光器件，所述空穴传输材料包括具有如式Ⅰ所示的化学结构的化合物：其中，R为给电子基团。本发明通过以氧环吖啶为核心，再配上其他给电子基团，以作为空穴传输材料，使得空穴传输材料具有较高的空穴迁移率以及合适的能级，提高了有机发光器件的发光效率，提高了显示效果。
• 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.
• C−H Activation/Borylation/Oxidation:  A One-Pot Unified Route To Meta-Substituted Phenols Bearing Ortho-/Para-Directing Groups
  作者：Robert E. Maleczka,、Feng Shi、Daniel Holmes、Milton R. Smith

  DOI：10.1021/ja0349857

  日期：2003.7.1

  An efficient one-pot C-H activation/borylation/oxidation protocol for the preparation of phenols is described. This method is particularly attractive for the generation of meta-substituted phenols bearing ortho-/para-directing groups, as such substrates are difficult to access by other phenol syntheses.