4-acetylphenyl 4-fluorobenzenesulfonate | 123412-35-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetylphenyl 4-fluorobenzenesulfonate
• 英文别名: p-Acetylphenyl p-fluorobenzenesulfonate；4-<<(4-fluorophenyl)sulfonyl>oxy>-1-acetophenone；4-Acetylphenyl p-fluorobenzenesulfonate；Benzenesulfonic acid, 4-fluoro-, 4-acetylphenyl ester；(4-acetylphenyl) 4-fluorobenzenesulfonate
• CAS: 123412-35-1
• 化学式: C₁₄H₁₁FO₄S
• 分子量: 294.303
• InChiKey: DVFIXEJLKMPOBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetylphenyl 4-fluorobenzenesulfonate 以98%的产率得到
  参考文献：
  名称：

  Percec Virgil, Bae Jin-Young, Zhao Mingyang, Hill Dale H., J. Org. Chem, 60 (1995) N 1, S 176-185

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氟苯磺酰氯 、 对羟基苯乙酮 以90%的产率得到4-acetylphenyl 4-fluorobenzenesulfonate
  参考文献：
  名称：

  磺酸查尔酮是新型的电压依赖性K +通道阻滞剂。

  摘要：

  合成了查尔酮衍生物1-17，并研究了它们的电压依赖性K +通道抑制活性。有效的K +通道阻滞剂显示为磺酸盐查耳酮9-17，其中磺酰氧基位于A环上。3'-（对氨基苯磺酰基羟基）-4-羟基查尔酮17（IC50 = 0.51 +/- 0.05 microM）是最有效的K +通道阻滞剂。

  DOI：

  10.1016/j.bmcl.2007.10.114

文献信息

• An Efficient Catalyst for Pd-Catalyzed Carbonylation of Aryl Arenesulfonates
  作者：Chaoxian Cai、Nelo R. Rivera、Jaume Balsells、Rick R. Sidler、J. Christopher McWilliams、C. Scott Shultz、Yongkui Sun

  DOI：10.1021/ol062208g

  日期：2006.10.1

  Aryl carboxylic esters were synthesized by Pd-catalyzed carbonylation of aryl p-fluorobenzenesulfonates or -tosylates. A unique Josiphos ligand was discovered through high-throughput catalyst screening, which was the key for the successful carbonylation of various substrates. This catalyst is effective and works well for both electron-rich and electron-poor aryl arenesulfonates. Isolated yields of up to 90% were obtained for aryl p-fluorobenzenesulfonates and -tosylates.
• Aryl Mesylates in Metal-Catalyzed Homocoupling and Cross-Coupling Reactions. 1. Functional Symmetrical Biaryls from Phenols via Nickel-Catalyzed Homocoupling of Their Mesylates
  作者：Virgil Percec、Jin-Young Bae、Mingyang Zhao、Dale H. Hill

  DOI：10.1021/jo00106a031

  日期：1995.1

  Aryl sulfonates including mesylate derived from phenols are converted in high yields to biaryls by homocoupling in the presence of catalytic amounts of zero-valent nickel catalysts generated in situ. This reaction provides the most convenient method for the synthesis of many functional symmetrical biaryls and was applied to the preparation of 2,2'-, 3,3'-, and 4,4'-disubstituted biphenyls and other biaryls. The influence of the electronic and steric effects of substituents attached in the ortho, meta, and para positions of aryl sulfonates and the nature of the sulfonate leaving group on the yield of homocoupled product as well as their influence on the extent of various side reactions were investigated. In addition, the influence of the effects of the polarity and dryness of solvent, halide ion source and concentration, and ratio of catalyst and ligand to aryl sulfonate are discussed.
• Palladium-catalyzed coupling of aryl arenesulfonates with organostannanes
  作者：Domenico Badone、Roberto Cecchi、Umberto Guzzi

  DOI：10.1021/jo00049a047

  日期：1992.11
• Chemoselective regulation of TREK2 channel: Activation by sulfonate chalcones and inhibition by sulfonamide chalcones
  作者：Eun-Jin Kim、Hyung Won Ryu、Marcus J. Curtis-Long、Jaehee Han、Jun Young Kim、Jung Keun Cho、Dawon Kang、Ki Hun Park

  DOI：10.1016/j.bmcl.2010.05.033

  日期：2010.7

  Although it has not been extensively studied, a significant volume of literature suggests that TREK2 will probably turn out to be an important channel in charge of tuning neuronal transmitter and hormone levels. Thus, pharmacological tools which can manipulate this channel, such as selective agonists are essential both in drug design and to further our understanding of this system. Our investigations have shown that sulfonate ('O') chalcone and sulfonamide ('N') chalcones regulate the TREK2 channel in remarkably different ways: sulfonamide chalcone 5 behaved as an inhibitor with an IC(50) of 62 mu M, whereas the sulfonate analogue 11 activated TREK2 with EC(50) value of 167 mu M. (C) 2010 Elsevier Ltd. All rights reserved.
• Palladium-catalyzed reduction of aryl sulfonates. Reduction versus hydrolysis selectivity control
  作者：Walter Cabri、Silvia De Bernardinis、Franco Francalanci、Sergio Penco、Roberto Santi

  DOI：10.1021/jo00288a062

  日期：1990.1