1-(2-(2,2,2-trifluoroethoxy)phenyl)ethanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2-(2,2,2-trifluoroethoxy)phenyl)ethanone
• 英文别名: 2'-(2,2,2-trifluoroethoxy)acetophenone；1-[2-(2,2,2-trifluoroethoxy)phenyl]ethanone
• 化学式: C₁₀H₉F₃O₂
• 分子量: 218.175
• InChiKey: HUIGQXCXQQNEGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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-(2-(2,2,2-trifluoroethoxy)phenyl)ethanone 、 对二甲氨基苯甲醛 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 以72%的产率得到(E)-3-(4-(dimethylamino)phenyl)-1-(2-(2,2,2-trifluoroethoxy)phenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture

  摘要：

  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。

  DOI：

  10.3390/molecules23051174
• 作为产物：
  描述：

  2,2,2-三氟乙基 对甲苯磺酸酯 、 2'-羟基苯乙酮 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.17h， 以68%的产率得到1-(2-(2,2,2-trifluoroethoxy)phenyl)ethanone
  参考文献：
  名称：

  Synthesis and Evaluation of Antiplasmodial Activity of 2,2,2-Trifluoroethoxychalcones and 2-Fluoroethoxy Chalcones against Plasmodium falciparum in Culture

  摘要：

  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。

  DOI：

  10.3390/molecules23051174

文献信息

• Expedient and efficient one pot synthesis of trifluoroethyl ethers from metal free 2,4,6-tris-(2,2,2-trifluoro-ethoxy)-[1,3,5] triazene
  作者：Shrawan Kumar Mangawa、Chiranjeev Sharma、Ashawani kumar Singh、Satish K. Awasthi

  DOI：10.1039/c5ra00618j

  日期：——

  An efficient synthesis of fluorinated alkyl and aryl ethers was achieved by the use of s-triazene derived fluorinated reagent 2,4,6-tris-(2,2,2-trifluoro-ethoxy)-[1,3,5] triazene (TriTFET).

  通过使用由s-三氮烯衍生的氟化试剂2,4,6-三(2,2,2-三氟乙氧基)-[1,3,5] 三氮烯(TriTFET)，实现了氟代烷基和芳基醚的高效合成。
• 6,5-BICYCLIC OCTAHYDROPYRROLOPYRIDINE OREXIN RECEPTOR ANTAGONISTS
  申请人：Kim Ronald M.

  公开号：US20170320874A1

  公开（公告）日：2017-11-09

  The present invention is directed to 6,5-bicyclic octahydropyrrolopyridine compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
• US9938276B2
  申请人：——

  公开号：US9938276B2

  公开（公告）日：2018-04-10
• [EN] 6,5-BICYCLIC OCTAHYDROPYRROLOPYRIDINE OREXIN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES OCTAHYDROPYRROLOPYRIDINES 6,5-BICYCLIQUES DU RÉCEPTEUR D'OREXINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2016100157A2

  公开（公告）日：2016-06-23

  The present invention is directed to 6,5-bicyclic octahydropyrrolopyridine compounds which are antagonists of orexin receptors. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which orexin receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which orexin receptors are involved.
• 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。