N-hydroxy-4-trifluoromethylbenzenesulfonamide

• 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-hydroxy-4-trifluoromethylbenzenesulfonamide
• 英文别名: N-hydroxy-4-(trifluoromethyl)benzenesulfonamide
• 化学式: C₇H₆F₃NO₃S
• 分子量: 241.191
• InChiKey: OSVZMWVLXCPDAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-hydroxy-4-trifluoromethylbenzenesulfonamide 以 水 为溶剂， 生成 一氧化二氮
  参考文献：
  名称：

  WO2007/109175

  摘要：

  公开号：
• 作为产物：
  描述：

  4-三氟甲基苯磺酰氯 在 4-二甲氨基吡啶 、 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 0.08h， 以57%的产率得到N-hydroxy-4-trifluoromethylbenzenesulfonamide
  参考文献：
  名称：

  Piloty’s acid derivative with improved nitroxyl-releasing characteristics

  摘要：

  Recent studies have shown that nitroxyl (HNO) ((HNO)-H-1/(NO)-N-3 ), which is the one-electron-reduced form of nitric oxide (NO), has unique biological activities, especially in the cardiovascular system, and HNO-releasing agents may have therapeutic potential. Since few HNO donors are available for use under physiological conditions, we synthesized and evaluated a series of Piloty's acid (PA) derivatives and evaluated their HNO-releasing activity under physiological conditions. N-Hydroxy-2-nitrobenzenesulfonamide (17) was the most efficient HNO donor among our synthesized PA derivatives, including the lead compound, 2-bromo-N-hydroxybenzenesulfonamide (2). The high HNO-releasing activity is suggested to be due to electronic and steric effects. Compound 17 may be a useful tool for biological experiments. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.062

文献信息

• Synthesis of Alkyl Aryl Sulfones via Reaction of N-Arylsulfonyl Hydroxyamines with Electron-Deficient Alkenes
  作者：Yunhui Bin、Ruimao Hua

  DOI：10.3390/molecules22010039

  日期：——

  Alkyl aryl sulfones were prepared in high yields via the reaction of N-arylsulfonyl hydroxylamines with electron-deficient alkenes. These reactions have the advantages of simplicity, easily available starting materials and mild reaction conditions.

  烷基芳基砜是通过N-芳基磺酰基羟胺与缺电子烯烃的反应高产率制备的。这些反应的优点是简单，容易获得的起始原料和温和的反应条件。
• 一种制备取代乙基芳基砜的方法
  申请人：清华大学

  公开号：CN105820096B

  公开（公告）日：2017-10-03

  本发明公开了一种制备取代乙基芳基砜的方法。该方法为：将式II所示化合物、式III所示化合物和碱混匀于溶剂中进行偶联反应，反应完毕得到R2′为‑CH2CH2R2的所述式I所示化合物；或者包括如下步骤：将式II所示化合物、丙炔酸乙酯和碱混匀于溶剂中进行偶联反应，反应完毕得到R2′为‑CH＝CHC＝OOCH2CH3的所述式I所示化合物。该方法、普适、便捷，反应体系简单，反应条件温和，并且非常容易放大到克级，反应原料的简单易得，所使用的碱和原料亦非常的廉价易得，原子利用率较高，溶剂毒性低。
• N-hydroxylsulfonamide derivatives as new physiologically useful nitroxyl donors
  申请人：Johns Hopkins University School of Medicine

  公开号：EP2489350A1

  公开（公告）日：2012-08-22

  The invention relates to N-hydroxysulfonamide derivatives that donate nitroxyl (HNO) under physiological conditions and are useful in treating and/or preventing the onset and/or development of diseases or conditions that are responsive to nitroxyl therapy, including heart failure and ischemia/reperfusion injury. Novel N-hydroxysulfonamide derivatives release NHO at a controlled rate under physiological conditions, and the rate of HNO release is modulated by varying the nature and location of functional groups on the N-hydroxysulfonamide derivatives.

  本发明涉及N-羟基磺酰胺衍生物，该衍生物可在生理条件下捐献硝酰（HNO），并可用于治疗和/或预防对硝酰治疗有反应的疾病或病症的发生和/或发展，包括心力衰竭和缺血/再灌注损伤。新型 N- 羟基磺酰胺衍生物可在生理条件下以可控速率释放 NHO，HNO 释放速率可通过改变 N- 羟基磺酰胺衍生物上官能团的性质和位置来调节。
• N-HYDROXYLSULFONAMIDE DERIVATIVES AS NEW PHYSIOLOGICALLY USEFUL NITROXYL DONORS
  申请人：The Johns Hopkins University

  公开号：EP3124471A1

  公开（公告）日：2017-02-01

  The invention relates to N-hydroxysulfonamide derivatives that donate nitroxyl (HNO) under physiological conditions and are useful in treating and/or preventing the onset and/or development of diseases or conditions that are responsive to nitroxyl therapy, including heart failure and ischemia/reperfusion injury. Novel N-hydroxysulfonamide derivatives release NHO at a controlled rate under physiological conditions, and the rate of HNO release is modulated by varying the nature and location of functional groups on the N-hydroxysulfonamide derivatives.

  本发明涉及N-羟基磺酰胺衍生物，该衍生物可在生理条件下捐献硝酰（HNO），并可用于治疗和/或预防对硝酰治疗有反应的疾病或病症的发生和/或发展，包括心力衰竭和缺血/再灌注损伤。新型 N- 羟基磺酰胺衍生物可在生理条件下以可控速率释放 NHO，HNO 释放速率可通过改变 N- 羟基磺酰胺衍生物上官能团的性质和位置来调节。
• Blue Light-Induced Coupling of N-Hydroxy Sulfonamides: An Efficient and Green Approach to Symmetrical Thiosulfonates
  作者：A. K. Pandey、A. Kumar、S. K. Srivastava

  DOI：10.1134/s1070428022060136

  日期：2022.6