4',N-dimethyl-4-nitrobenzenesulfonanilide | 211676-02-7

• 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: 4',N-dimethyl-4-nitrobenzenesulfonanilide
• 英文别名: N-methyl-4-nitro-N-(p-tolyl)benzenesulfonamide；N-methyl-N-(4-methylphenyl)-4-nitrobenzenesulfonamide
• CAS: 211676-02-7
• 化学式: C₁₄H₁₄N₂O₄S
• 分子量: 306.342
• InChiKey: LERDDYBGAMSYLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4',N-dimethyl-4-nitrobenzenesulfonanilide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以74%的产率得到4-amino-N-methyl-N-(4-methylphenyl)benzenesulfonamide
  参考文献：
  名称：

  Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors

  摘要：

  In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2006.10.029
• 作为产物：
  描述：

  对硝基苯磺酰氯 、 N,N-二甲基对甲苯胺 在 cadmium sulphide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 以95%的产率得到4',N-dimethyl-4-nitrobenzenesulfonanilide
  参考文献：
  名称：

  纳米级CdS作为可重复使用的光催化剂：通过可见光诱导的N-脱烷基化和C–H活化过程，叔胺与芳基磺酰氯之间不同反应途径的研究

  摘要：

  已经发现，在可见光辐射下，在硫化镉纳米颗粒存在下，磺酰氯和叔胺反应的最终产物高度依赖于所应用的反应条件。有趣的是，随着反应条件的改变，进行了不同的途径（可见光诱导的N-脱烷基或sp 3和sp 2C–H活化）导致产生不同的产物，例如仲胺和各种磺酰基化合物。值得注意的是，所有这些反应都是在可见光辐射下和在没有良性溶剂的情况下在无溶剂或无溶剂条件下的空气气氛下进行的。在这项研究过程中，CdS纳米颗粒作为可负担的，多相的和可回收的光催化剂被设计，成功合成并充分表征并应用于这些方案。在这些研究中，由叔胺氧化产生的中间体在光致电子转移（PET）过程中被捕获。使用可见光辐照作为可再生能源的同时，反应可在各种底物上有效地进行，从而在相对短的时间内以良好至极好的收率得到相应的产物。这些过程中的大多数都是新颖​​的，或者在成本效益，安全性和简化性方面优于已发布的报告。

  DOI：

  10.1021/acs.joc.0c02263

文献信息

• Study on Radical Amidation onto Aromatic Rings with (Diacyloxyiodo)arenes
  作者：Hideo Togo、Yoichiro Hoshina、Takahito Muraki、Hiromasa Nakayama、Masataka Yokoyama

  DOI：10.1021/jo980450y

  日期：1998.7.1

  Sulfonamides of primary amines bearing an aromatic ring at the gamma-position were treated with (diacyloxyiodo)arenes and:iodine under irradiation conditions with;a tungsten-lamp to give the corresponding 1,2,3,4-tetrahydroquinoline derivatives in moderate to good yields. Here, the reactivity depends on the Z-group (protecting group) of the starting amides. Under the same reaction conditions, some sulfonamides were treated with (diacetoxyiodo)benzene and iodine in the presence of aromatics to give the corresponding N-arylated amides. These reactions proceed through the intramolecular and intermolecular amidations onto aromatic rings via the sulfonamidyl radicals formed.
• Nanosized CdS as a Reusable Photocatalyst: The Study of Different Reaction Pathways between Tertiary Amines and Aryl Sulfonyl Chlorides through Visible-Light-Induced N-Dealkylation and C–H Activation Processes
  作者：Somayeh Firoozi、Mona Hosseini-Sarvari

  DOI：10.1021/acs.joc.0c02263

  日期：2021.2.5

  It has been found that the final products of the reaction of sulfonyl chlorides and tertiary amines in the presence of cadmium sulfide nanoparticles under visible light irradiation are highly dependent on the applied reaction conditions. Interestingly, with the change of a reaction condition, different pathways were conducted (visible-light-induced N-dealkylation or sp3 and sp2 C–H activation) that

  已经发现，在可见光辐射下，在硫化镉纳米颗粒存在下，磺酰氯和叔胺反应的最终产物高度依赖于所应用的反应条件。有趣的是，随着反应条件的改变，进行了不同的途径（可见光诱导的N-脱烷基或sp 3和sp 2C–H活化）导致产生不同的产物，例如仲胺和各种磺酰基化合物。值得注意的是，所有这些反应都是在可见光辐射下和在没有良性溶剂的情况下在无溶剂或无溶剂条件下的空气气氛下进行的。在这项研究过程中，CdS纳米颗粒作为可负担的，多相的和可回收的光催化剂被设计，成功合成并充分表征并应用于这些方案。在这些研究中，由叔胺氧化产生的中间体在光致电子转移（PET）过程中被捕获。使用可见光辐照作为可再生能源的同时，反应可在各种底物上有效地进行，从而在相对短的时间内以良好至极好的收率得到相应的产物。这些过程中的大多数都是新颖​​的，或者在成本效益，安全性和简化性方面优于已发布的报告。
• Analgesic agents without gastric damage: Design and synthesis of structurally simple benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors
  作者：Xiaoxia Zheng、Hiroyuki Oda、Kayo Takamatsu、Yukio Sugimoto、Akihiro Tai、Eiichi Akaho、Hamed Ismail Ali、Toshiyuki Oshiki、Hiroki Kakuta、Kenji Sasaki

  DOI：10.1016/j.bmc.2006.10.029

  日期：2007.1

  In order to create novel analgesic agents without gastric disturbance, structurally simple cyclooxygenase-1 (COX-1) inhibitors with a benzenesulfonanilide skeleton were designed and synthesized. As a result, compounds 11f and 15a, which possess a p-amino group on the benzenesulfonyl moiety and p-chloro group on the anilino moiety, showed COX-1-selective inhibition. Moreover compound 11f, which is the most potent compound in this study showed more potent analgesic activity than that of aspirin at 30 mg/kg by po. The anti-inflammatory activity and gastric damage, however, were very weak or not detectably different from aspirin. Since the structure of our COX-1 inhibitors are very simple, they may be useful as lead compounds for superior COX-1 inhibitors as analgesic agents without gastric disturbance. (c) 2006 Published by Elsevier Ltd.