1-(3-(2,2,2-三氟乙氧基)苯基)乙酮 | 1017025-91-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(3-(2,2,2-三氟乙氧基)苯基)乙酮
• 英文名称: 1-(3-(2,2,2-trifluoroethoxy)phenyl)ethanone
• 英文别名: 1-(3-(2,2,2-trifluoroethoxy)phenyl)ethan-1-one；1-[3-(2,2,2-Trifluoroethoxy)phenyl]ethan-1-one；1-[3-(2,2,2-trifluoroethoxy)phenyl]ethanone
• CAS: 1017025-91-0
• 化学式: C₁₀H₉F₃O₂
• 分子量: 218.175
• InChiKey: FHWHKULAMSCZGB-UHFFFAOYSA-N

物化性质

• 沸点：
  231.3±40.0 °C(Predicted)
• 密度：
  1.226±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(3-(2,2,2-三氟乙氧基)苯基)乙酮 在 甲醇 、 sodium tetrahydroborate 作用下， 以54.68 %的产率得到1-[3-(2,2,2-Trifluoroethoxy)phenyl]ethanol
  参考文献：
  名称：

  [EN] SUBSTITUTED 3,4-DIHYDROQUINOLINONE INHIBITORS OF TSHR
  [FR] INHIBITEURS DE TSHR SUBSTITUÉS DE 3,4-DIHYDROQUINOLINONE

  摘要：

  Disclosed are compounds that are thyroid stimulating hormone receptor antagonists, and methods useful for preventing or treating a thyroid disease.

  公开号：

  WO2024026076A2
• 作为产物：
  描述：

  2,2,2-三氟乙醇 、 3-乙酰基苯硼酸 在 4-二甲氨基吡啶 、 氧气 、 copper(II) acetate monohydrate 作用下， 反应 1.0h， 以53%的产率得到1-(3-(2,2,2-三氟乙氧基)苯基)乙酮
  参考文献：
  名称：

  通过CF 3 CH 2 OH与芳基和杂芳基硼酸的铜催化偶联轻松合成三氟乙基芳基醚

  摘要：

  已经开发出一种有效的铜催化三氟乙醇与各种芳基和杂芳基硼酸的Chan-Lam反应。该研究提供了一种在温和条件下以中等至良好收率合成三氟乙基芳基醚的实用方法。

  DOI：

  10.1016/j.tetlet.2015.06.066

文献信息

• Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture
  作者：Kavita Devi、Vinoth Rajendran、Ayushee、T. Rangarajan、Rishi Singh、Prahlad Ghosh、Manjula Singh

  DOI：10.3390/molecules23051174

  日期：——

  A new class of compounds comprising two series of chalcones with 2,2,2-trifluoroethoxy group and 2-fluoroethoxy groups were synthesized and screened for in vitro antiplasmodial activity against Plasmodium falciparum (3D7) using the [3H] hypoxanthine incorporation inhibition assay. Chalcones with 2,2,2-trifluoroethoxy groups substituted on the p- and m-positions of the 1-phenyl ring showed weak antiplasmodial activity, while compounds substituted on the o-position of the 1-phenyl ring displayed enhanced antiplasmodial activity, thus indicating that 2,2,2-trifluoroethoxy groups on the 1-phenyl ring of chalcones show position-dependent antiplasmodial activity. Of the 34 compounds synthesized, chalcones 3a and 3f exhibited significant inhibitory effects, with IC50 values of 3.0 μg/mL and 2.2 μg/mL, respectively. Moreover, these compounds 3a and 3f showed profound antiplasmodial activity in combination with artemisinin in vitro. The most active molecules, 3a, and 3f, were further assessed for their cytotoxicity towards mammalian Vero cells and the selectivity index (SI) values are 8.6, and 8.2 respectively, being considered non-toxic. We also studied the antiplasmodial activity of 2-fluoroethoxychalcones to discern the effect of the number of fluorine atoms in the fluoroethoxy group. Our results showed that chalcones with 2-fluoroethoxy group on the 1-phenyl ring exhibited more enhanced inhibitory effects on the growth of parasites than their trifluoro analogues, which reveals that monofluoroethoxy group is generally more effective than trifluoroethoxy group in the inhibition of parasite growth. Thus o-2,2,2-trifluoroethoxychalcones (Series 3) and 2-fluoroethoxychalcones may serve as good antiplasmodial candidates for future further development.

  一类新化合物，包含两系列查耳酮，分别带有2,2,2-三氟乙氧基和2-氟乙氧基，被合成并在体外针对恶性疟原虫（3D7株）进行了抗疟活性筛选，采用[3H]次黄嘌呤掺入抑制试验。在1-苯环的p-和m-位上带有2,2,2-三氟乙氧基的查耳酮显示出较弱的抗疟活性，而在1-苯环的o-位上带有该基团的化合物则展现出增强的抗疟活性，表明在查耳酮的1-苯环上的2,2,2-三氟乙氧基具有位点依赖性的抗疟活性。在合成的34个化合物中，查耳酮3a和3f表现出显著的抑制效果，IC50值分别为3.0 μg/mL和2.2 μg/mL。此外，化合物3a和3f与青蒿素在体外联合应用时显示出深刻的抗疟活性。活性最强的分子3a和3f，对其在哺乳动物Vero细胞上的细胞毒性进行了评估，选择性指数（SI）值分别为8.6和8.2，被认为无毒。我们还研究了2-氟乙氧基查耳酮的抗疟活性，以了解氟乙氧基中氟原子数量的影响。结果显示，1-苯环上带有2-氟乙氧基的查耳酮对寄生虫生长的抑制效果比其三氟类似物更为增强，表明单氟乙氧基在抑制寄生虫生长方面通常比三氟乙氧基更有效。因此，o-2,2,2-三氟乙氧基查耳酮（系列3）和2-氟乙氧基查耳酮可能是未来进一步开发的优秀抗疟候选药物。
• Synthesis of Fluorinated Alkyl Aryl Ethers by Palladium-Catalyzed C–O Cross-Coupling
  作者：Robert Szpera、Patrick G. Isenegger、Maxime Ghosez、Natan J. W. Straathof、Rosa Cookson、David C. Blakemore、Paul Richardson、Véronique Gouverneur

  DOI：10.1021/acs.orglett.0c02347

  日期：2020.8.21

  cross-coupling of (hetero)aryl bromides with fluorinated alcohols using the commercially available precatalyst tBuBrettPhos Pd G3 and Cs2CO3 in toluene. This Pd-catalyzed coupling features a short reaction time, excellent functional group tolerance, and compatibility with electron-rich and -poor (hetero)arenes. The method provides access to 18F-labeled trifluoroethyl ethers by cross-coupling with [

  在本文中，我们报告了一种高效的方案，可使用市售的预催化剂t BuBrettPhos Pd G3和Cs 2 CO 3在甲苯中将（杂）芳基溴化物与氟化醇交叉偶联。这种钯催化的偶联反应具有反应时间短，对官能团的耐受性强以及与富电子和贫电子（杂）芳烃相容的特点。该方法通过与[ 18 F]三氟乙醇交叉偶联而获得18 F-标记的三氟乙基醚。
• [EN] ARYLAMIDE DERIVATIVES AS TTX-S BLOCKERS<br/>[FR] DÉRIVÉS D'ARYLAMIDE EN TANT QU'AGENTS BLOQUANTS DE TTX-S
  申请人：RAQUALIA PHARMA INC

  公开号：WO2012053186A1

  公开（公告）日：2012-04-26

  The present invention relates to arylamide derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及具有对电压门控钠通道（如TTX-S通道）具有阻塞活性的芳基酰胺衍生物，用于治疗或预防涉及电压门控钠通道的疾病和疾病。该发明还涉及包含这些化合物的药物组合物以及在预防或治疗涉及电压门控钠通道的这类疾病中使用这些化合物和组合物。
• ARYLAMIDE DERIVATIVES AS TTX-S BLOCKERS
  申请人：Yamagishi Tatsuya

  公开号：US20140336377A1

  公开（公告）日：2014-11-13

  The present invention relates to arylamide derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及一种芳基酰胺衍生物，其具有阻断电压门控钠通道（如TTX-S通道）的活性，并且在涉及电压门控钠通道的疾病和疾病的治疗或预防中有用。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在涉及电压门控钠通道的这种疾病的预防或治疗中的使用。
• Arylamide derivatives as TTX-S blockers
  申请人：Yamagishi Tatsuya

  公开号：US09302991B2

  公开（公告）日：2016-04-05

  The present invention relates to arylamide derivatives which have blocking activities of voltage gated sodium channels as the TTX-S channels, and which are useful in the treatment or prevention of disorders and diseases in which voltage gated sodium channels are involved. The invention also relates to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which voltage gated sodium channels are involved.

  本发明涉及芳基酰胺衍生物，其具有阻断电压门控钠通道（TTX-S通道）的活性，并且在治疗或预防涉及电压门控钠通道的疾病和疾病方面有用。本发明还涉及包含这些化合物的制药组合物以及在预防或治疗涉及电压门控钠通道的疾病方面使用这些化合物和组合物。