N-(3,5-dimethylphenyl)-4-nitrobenzenesulfonamide | 349397-08-6

• 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-(3,5-dimethylphenyl)-4-nitrobenzenesulfonamide
• 英文别名: 4-nitro-benzenesulfonic acid-(3,5-dimethyl-anilide)；4-Nitro-benzolsulfonsaeure-(3,5-dimethyl-anilid)；N-(3,5-Dimethylphenyl)-4-nitro-1-benzenesulfonamide
• CAS: 349397-08-6
• 化学式: C₁₄H₁₄N₂O₄S
• mdl: MFCD01212697
• 分子量: 306.342
• InChiKey: WFZYFMYIHKNZPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 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：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(3,5-dimethylphenyl)-4-nitrobenzenesulfonamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以69%的产率得到4-amino-N-(3,5-dimethylphenyl)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：

  1-氨基-3,5-二甲苯 、 对硝基苯磺酰氯 在 吡啶 作用下， 反应 4.0h， 生成 N-(3,5-dimethylphenyl)-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  使用仲铵盐有机催化剂对苯胺进行高度原位选择性氯化

  摘要：

  描述了苯胺的有机催化，高度简便，有效和区域选择性邻氯化反应。已经使用仲氯化铵盐作为催化剂，并且该反应可以在室温下进行而无需保护空气和湿气。另外，该反应易于扩展，并且催化剂可以再循环和再利用。该催化方案已用于高效合成高效c-Met激酶抑制剂。机理研究表明，仲氯化铵盐的独特结构特征对于亲电子邻氯化反应的催化和区域选择性均很重要。

  DOI：

  10.1002/anie.201607388

文献信息

• Amine organocatalysts for highly <i>ortho</i>-selective chlorination of anilines with sulfuryl chloride
  作者：Xinzhe Wang、Zhihuang Chen、Qingqing Liu、Wenqing Lin、Xiaodong Xiong

  DOI：10.1039/d2cc05320a

  日期：——

  A metal catalyst free approach for regioselective ortho-chlorination of anilines has been developed using a secondary amine as the organocatalyst and sulfuryl chloride as the halogen source under mild conditions. A wide range of substrates were compatible with this catalytic system. In addition, this catalytic protocol has been applied to the efficient synthesis of bioactive compounds and modification

  使用仲胺作为有机催化剂和硫酰氯作为卤素源，在温和条件下开发了一种用于苯胺区域选择性邻氯化的无金属催化剂方法。多种底物与该催化系统相容。此外，该催化方案已应用于生物活性化合物的高效合成和药物衍生物的修饰。进一步的研究表明阴离子三氯化物是邻位选择性的原因。
• Behnisch, Chemische Berichte, 1948, vol. 81, p. 297,302
  作者：Behnisch

  DOI：——

  日期：——
• Highly<i>ortho</i>-Selective Chlorination of Anilines Using a Secondary Ammonium Salt Organocatalyst
  作者：Xiaodong Xiong、Ying-Yeung Yeung

  DOI：10.1002/anie.201607388

  日期：2016.12.23

  An organocatalytic, highly facile, efficient, and regioselective ortho‐chlorination of anilines is described. A secondary ammonium chloride salt has been employed as the catalyst and the reaction can be conducted at room temperature without protection from air and moisture. In addition, the reaction is readily scalable and the catalyst can be recycled and reused. This catalytic protocol has been applied

  描述了苯胺的有机催化，高度简便，有效和区域选择性邻氯化反应。已经使用仲氯化铵盐作为催化剂，并且该反应可以在室温下进行而无需保护空气和湿气。另外，该反应易于扩展，并且催化剂可以再循环和再利用。该催化方案已用于高效合成高效c-Met激酶抑制剂。机理研究表明，仲氯化铵盐的独特结构特征对于亲电子邻氯化反应的催化和区域选择性均很重要。
• 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.