N-(2-(4-fluorobenzoyl)phenyl)-4-methylbenzenesulfonamide | 934560-46-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-(4-fluorobenzoyl)phenyl)-4-methylbenzenesulfonamide
• 英文别名: N-[2-(4-fluorobenzoyl)phenyl]-4-methylbenzenesulfonamide
• CAS: 934560-46-0
• 化学式: C₂₀H₁₆FNO₃S
• 分子量: 369.416
• InChiKey: XDNIDDRHEOHFQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(4-fluorobenzoyl)phenyl)-4-methylbenzenesulfonamide 在 氢氧化钾 、 碘苯二乙酸 、 硫酸 、 碘 、 4-甲基苯磺酸吡啶 作用下， 以 1,4-二氧六环 、 四氯化碳 、 水 为溶剂， 生成 2-cyclopropyl-4-(4-fluorophenyl)-3-iodoquinoline
  参考文献：
  名称：

  A novel synthetic method of HMG-CoA reductase inhibitor NK-104 via a hydroboration-cross coupling sequence

  摘要：

  The regioselective hydroboration of ethyl (3R, 5S)-3,5-isopropylidenedioxy-6-heptynoate, followed by the cross-coupling reaction with an aryl halide, provides ethyl (3R, 5S, 6E)-7-aryl-3,5-isopropylidenedioxy-6-heptenoate, a precursor of a highly potent HMG-CoA reductase inhibitor NK-104.

  DOI：

  10.1016/s0040-4039(00)61407-7
• 作为产物：
  描述：

  对甲苯磺酰氯 在 氯 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 N-(2-(4-fluorobenzoyl)phenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  一种2-氨基-4＇-氟-二苯甲酮的合成方法

  摘要：

  本发明公开了一种2‑氨基‑4＇‑氟‑二苯甲酮的合成方法，包括如下步骤：邻甲基苯胺与对甲苯磺酰氯进行酰胺化反应得到4‑甲基‑N‑(2‑甲基苯基)苯磺酰胺；然后经氯气氯化，与氟苯发生傅克反应，再经水解得到N‑(2‑(4‑氟苯甲酰基)苯基)‑4‑甲基苯磺酰胺；最后经浓硫酸脱保护得到2‑氨基‑4'‑氟‑二苯甲酮。本发明起始原料廉价易得，成本低，操作方便，适合工业化生产，合成路线绿色环保，收率高，制备得到的2‑氨基‑4'‑氟‑二苯甲酮纯度好。

  公开号：

  CN109574863B

文献信息

• Electrochemical intramolecular N(sp²)–H/N(sp³)–H coupling for the synthesis of 1<i>H</i>-indazoles
  作者：Qiang Zhong、Pei-Long Wang、Hui Gao、Fang Ma、Youqing Yang、Hongji Li

  DOI：10.1039/d3gc00380a

  日期：——

  The electrochemical synthesis of 1H-indazoles via an intramolecular N(sp2)–H/N(sp3)–H coupling reaction at room temperature is first described. The transition metal-free electrochemical cyclization features the use of commercially available NH3 as the nitrogen source and a broad substrate scope, thus affording a wide range of substituted 1H-indazoles in moderate to good yields. Both the control experiments

  首先描述了在室温下通过分子内 N(sp 2 )–H/N(sp 3 )–H 偶联反应电化学合成 1 H-吲唑。无过渡金属电化学环化的特点是使用市售的 NH 3作为氮源和广泛的底物范围，从而以中等到良好的产率提供范围广泛的取代 1 H-吲唑。控制实验和机理研究都支持所提出的这种电化学环化反应机理。
• Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: a new series of selective COX-2 inhibitors
  作者：Wenhui Hu、Zongru Guo、Fengming Chu、Aiping Bai、Xiang Yi、Guifang Cheng、Jing Li

  DOI：10.1016/s0968-0896(03)00046-4

  日期：2003.4

  A new series of substituted 2-sulfonyphenyl-3-phenyl-indole derivatives were synthesized and evaluated for their ability to inhibit COX-2 and COX-lenzymes. Most of the compounds synthesized were found to be highly potent and selective inhibitors of COX-2. This work led to the discovery of 2-aminosulfonylphenyl-3-phenyl-indole 5a which possesses higher activity and selectivity for COX-2 than Celecoxib both in vitro and in vivo. (C) 2003 Elsevier Science Ltd. All rights reserved.
• From Five- to Six-Membered Rings:  3,4-Diarylquinolinone as Lead for Novel p38MAP Kinase Inhibitors
  作者：Christian Peifer、Katrin Kinkel、Mohammed Abadleh、Dieter Schollmeyer、Stefan Laufer

  DOI：10.1021/jm061097o

  日期：2007.3.1

  In this study we describe the design, synthesis, and biological evaluation of 3-(4-fluorophenyl)-4-pyridin-4-ylquinoline-2(1H)-one (5) as a new inhibitor of MAPK with a p38 alpha MAPK IC50 of 1.8 mu M. By keeping the common vicinal pyridine/4-F-phenyl pharmacophore, such as in prototypical imidazole 20 or isoxazole 13 but in 5 connected to the six-membered quinoline core, we were particularly interested in comparing biological activity, details of molecular geometry, and different binding modes of these compounds. Compounds 20 and 13 were active both in the p38 alpha- and JNK3-assay, whereas 5 was selective for p38 alpha, with no JNK3 inhibition. By comparing the X-ray structures of the compounds, we found a significantly larger distance between the pyridine and the 4-F-phenyl moiety in five-membered core structures relevant for ligand-protein interactions. Molecular modeling studies support the results based on differences in the ATP pockets of p38 alpha and JNK3. Because most five-membered core based p38 alpha inhibitors show also activity for JNK3, compound 5 is an interesting lead for selective p38 alpha inhibitors.
• 1-Acryloyl-2-cyanoindole: A Skeleton for Visible-Light-Induced Cascade Annulation
  作者：An-Xiang Huang、Hu-Lin Zhu、Fan-Lin Zeng、Xiao-Lan Chen、Xian-Qiang Huang、Ling-Bo Qu、Bing Yu

  DOI：10.1021/acs.orglett.2c00927

  日期：2022.4.29
• Visible-Light-Promoted Phosphorylation/Cyclization of 1-Acryloyl-2-cyanoindoles in Green Solvent
  作者：An-Xiang Huang、Yi-Rui Fu、Hu-Lin Zhu、Fan-Lin Zeng、Xiao-Lan Chen、Shi Tang、Ling-Bo Qu、Bing Yu

  DOI：10.1021/acs.joc.2c01890

  日期：2022.11.4