2-(3-氟苯基)-1-[4-(甲硫基)苯基]乙酮 | 301699-27-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 2-(3-氟苯基)-1-[4-(甲硫基)苯基]乙酮
• 英文名称: 2-(3-fluorophenyl)-1-(4-methylsulfanylphenyl)ethanone
• 英文别名: 2-(3-fluorophenyl)-1-(4-(methylthio)phenyl)ethanone；2-(3-fluorophenyl)-1-[4-(methylthio)phenyl]ethanone；2-(3-fluorophenyl)-1-{4-(methylthio)phenyl}-ethanone
• CAS: 301699-27-4
• 化学式: C₁₅H₁₃FOS
• mdl: MFCD22255894
• 分子量: 260.332
• InChiKey: JLKKDKSESPEKBB-UHFFFAOYSA-N

物化性质

• 沸点：
  399.0±27.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-氟苯基)-1-[4-(甲硫基)苯基]乙酮 在 magnesium monoperoxyphthalate hexahydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以71%的产率得到2-(3-fluorophenyl)-1-(4-methanesulfonylphenyl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2-Phenylpyran-4-ones:  A New Class of Orally Active Cyclooxygenase-2 Inhibitors

  摘要：

  A series of 2-phenylpyran-4-ones were prepared and evaluated for their ability to inhibit cyclooxygenase-2 (COX-2). Extensive structure-activity relationship work was carried out within this series, and a number of potent and selective COX-2 inhibitors were identified. Compounds having a p-methylsulfone group at the 2-phenyl ring showed the best COX-2 inhibitory activity. The introduction of a substituted phenoxy ring at position 3 enhanced both the in vitro and in vivo activity within the series. A selected group of 3-phenoxypyran-4-ones exhibited excellent activity in an experimental model of pyresis. The in vivo antiinflammatory activity of these compounds was confirmed with the evaluation of their antiarthritic and analgesic effectiveness. Moreover, their pharmacokinetic profile in rats is compatible with a once a day administration by oral route in humans. Within this novel series, compounds 21, 31, 34, and 35 have been selected for further preclinical. and clinical evaluation.

  DOI：

  10.1021/jm049882t
• 作为产物：
  描述：

  茴香硫醚 、 间氟苯乙酰氯间氟苯乙酰氯 在 茴香硫醚 作用下， 以88.3的产率得到2-(3-氟苯基)-1-[4-(甲硫基)苯基]乙酮
  参考文献：
  名称：

  [EN] METHOD FOR PREPARING 4-(3-(3-FLUOROPHENYL)-5,5-DIMETHYL-4-OXO-4,5-DIHYDROFURAN-2-YL)BENZENESULFONAMIDE
  [FR] PROCÉDÉ DE PRÉPARATION DE 4-(3-(3-FLUOROPHÉNYL)-5,5-DIMÉTHYL-4-OXO-4,5-DIHYDROFURAN-2-YL)BENZÈNESULFONAMIDE
  [KO] 4-(3-(3-플루오로페닐)-5,5-디메틸-4-옥소-4,5-디하이드로푸란-2-일)벤젠설폰아마이드의 제조 방법

  摘要：

  这项发明涉及制造4-(3-(3-氟苯基)-5,5-二甲基-4-氧代-4,5-二氢呋喃-2-基)苯磺酰胺的方法。使用本发明的方法，可以以非常简单和经济的方式高产量地大规模生产该化合物。

  公开号：

  WO2015080435A1

文献信息

• 4,5-diaryl-3(2H)-furanone derivatives as cyclooxygenase-2 inhibitors
  申请人：Pacific Corporation

  公开号：US06492416B1

  公开（公告）日：2002-12-10

  The present invention provides a novel class of 4,5-diaryl-3(2H)-furanone derivatives, which inhibit strongly and selectively COX-2 over COX-1. They are useful to treat inflammation, inflammation-associated disorders, and COX-2 mediated diseases.

  本发明提供了一类新型的4,5-二芳基-3(2H)-呋喃酮衍生物，其强烈且选择性地抑制COX-2而不抑制COX-1。它们可用于治疗炎症、与炎症相关的疾病和COX-2介导的疾病。
• Benzylic Aroylation of Toluenes Mediated by a LiN(SiMe₃)₂/Cs⁺ System
  作者：Yuanyun Gu、Zhen Zhang、Yan-En Wang、Ziteng Dai、Yaqi Yuan、Dan Xiong、Jie Li、Patrick J. Walsh、Jianyou Mao

  DOI：10.1021/acs.joc.1c02446

  日期：2022.1.7

  Chemoselective deprotonative functionalization of benzylic C–H bonds is challenging, because the arene ring contains multiple aromatic C(sp2)–H bonds, which can be competitively deprotonated and lead to selectivity issues. Recently it was found that bimetallic [MN(SiMe3)2 M = Li, Na]/Cs+ combinations exhibit excellent benzylic selectivity. Herein, is reported the first deprotonative addition of toluenes

  苄基 C-H 键的化学选择性去质子官能化具有挑战性，因为芳烃环含有多个芳香族 C(sp 2 )-H 键，它们可以竞争性去质子化并导致选择性问题。最近发现双金属[MN(SiMe 3 ) 2 M = Li, Na]/Cs +组合表现出优异的苄基选择性。本文报道了由 LiN(SiMe 3 ) 2介导的甲苯对 Weinreb 酰胺的第一次去质子化加成/CsF 用于合成多种 2-芳基苯乙酮。令人惊讶的是，简单的苯甲酸甲酯也可以在类似条件下与甲苯反应生成 2-芳基苯乙酮，而无需双重加成得到叔醇产物。这一发现极大地增加了这种化学的实用性和影响力。一些在苄基去质子化方面具有挑战性的底物，例如氟和甲氧基取代的甲苯，可以选择性地转化为 2-芳基苯乙酮。3-氟甲苯的苄基去质子化的价值通过在 Polmacoxib 制备中的关键中间体的合成得到证明。
• 一种非甾体抗炎药泊马昔布关键中间体的合 成方法
  申请人：康化（上海）新药研发有限公司

  公开号：CN106977475B

  公开（公告）日：2019-04-19

  本发明提供一种非甾体抗炎药泊马昔布关键中间体的合成方法，包括如下步骤：步骤S1，将硝基苯酚溶解在有机溶剂A中，0‑10℃下，滴加有机碱A，然后滴加溴异丁酰溴，滴加完毕后，室温反应0.2‑2小时，然后加水淬灭反应，分出有机相，经后处理步骤，打浆后得到化合物1；步骤S2，将化合物1和化合物2溶解在四氢呋喃中，降温到‑20℃，滴加有机碱B后反应，加水淬灭反应，加有机溶剂B萃取，合并有机相，用0.5M氢氧化钠溶液洗，然后干燥，浓缩，打浆得所述泊马昔布关键中间体。本发明所使用的溴异丁酸硝基苯酚酯具有合成简单，收率高，成本低，设备要求低，不产生剧毒物氰化物，污染少，储存方便等优点。
• 酰基三氮唑类化合物及其制备方法和应用
  申请人：宁波百思佳医药科技有限公司

  公开号：CN106866558B

  公开（公告）日：2019-07-30

  本发明公开了一种酰基三氮唑类化合物及其制备方法和应用，该酰基三氮唑类化合物的结构如式(I)所示，式(Ⅰ)中，X为Cl、Br、I或OSO2R3；R3为C1～C4烷基、苯基或取代的苯基；R1和R2分别独立地为H、卤素、CN、NO2、C1～C6烷基、C1～C6烷氧基、C1～C6烷硫基或NR4R5，其中，R4和R5分别独立地为C1～C6烷基。应用该化合物合成泊马昔布中间体，收率高，成本低，不副产氰化合物安全环保，适合产业化生产。
• Synthesis and biological evaluation of 2,3-diarylpyrazines and quinoxalines as selective COX-2 inhibitors
  作者：Sunil K. Singh、V. Saibaba、V. Ravikumar、Santosh V. Rudrawar、Pankaj Daga、C.Seshagiri Rao、V. Akhila、P. Hegde、Y.Koteswar Rao

  DOI：10.1016/j.bmc.2004.01.033

  日期：2004.4

  Several 2,3-diaryl pyrazines and quinoxalines with 4-sulfamoyl (SO2NH2)/methylsulfonyl (SO2Me)-phenyl pharmaco-phores have been synthesized and evaluated for the cyclooxygenase (COX-1/COX-2) inhibitory activity. Smaller groups such as methoxy, methyl and fluoro when substituted at/around position-4 of the adjacent phenyl ring, have great impact on the selective COX-2 inhibitory activity of the series. Many potential compounds were obtained from a brief structure-activity relationship (SAR) study. Two of these, compounds 11 and 25 exhibited excellent in vivo activity in the established animal model of inflammation. Since compound 25 possessed an amenable sulfonamide group, two of its prodrugs 48 and 49 were also synthesized. Both of them have excellent in vivo potential, and represent a new class of COX-2 inhibitor. (C) 2004 Elsevier Ltd. All rights reserved.