N-ethyl-4-nitro-N-phenylbenzenesulfonamide | 211675-98-8

• 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-ethyl-4-nitro-N-phenylbenzenesulfonamide
• 英文别名: 4-nitro-benzenesulfonic acid-(N-ethyl-anilide)；4-Nitro-benzolsulfonsaeure-(N-aethyl-anilid)
• CAS: 211675-98-8
• 化学式: C₁₄H₁₄N₂O₄S
• mdl: MFCD01211974
• 分子量: 306.342
• InChiKey: UNCKFYGLTOYWNU-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：
  4
• 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：

  N-ethyl-4-nitro-N-phenylbenzenesulfonamide 在 tin(ll) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以75%的产率得到4-氨基-N-乙基-N-苯基苯磺酰胺
  参考文献：
  名称：

  Sulfamoyl-4-oxoquinoline-3-carboxamides: Novel potentiators of defective ΔF508-cystic fibrosis transmembrane conductance regulator chloride channel gating

  摘要：

  The synthesis of a small collection of sulfamoyl-4-oxoquinoline-3-carboxamides is described for use as correctors of defective gating of the Delta F508-cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. Several compounds with submicromolar potency were obtained. N-Ethyl 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (7b) was found to be the most effective sulfonamide corrector of defective Delta F508-CFTR gating. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.050
• 作为产物：
  描述：

  N-乙基苯胺 、 对硝基苯磺酰氯 在 TEA 作用下， 反应 1.0h， 以90%的产率得到N-ethyl-4-nitro-N-phenylbenzenesulfonamide
  参考文献：
  名称：

  Sulfamoyl-4-oxoquinoline-3-carboxamides: Novel potentiators of defective ΔF508-cystic fibrosis transmembrane conductance regulator chloride channel gating

  摘要：

  The synthesis of a small collection of sulfamoyl-4-oxoquinoline-3-carboxamides is described for use as correctors of defective gating of the Delta F508-cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel. Several compounds with submicromolar potency were obtained. N-Ethyl 6-(ethylphenylsulfamoyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide (7b) was found to be the most effective sulfonamide corrector of defective Delta F508-CFTR gating. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.10.050

文献信息

• 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。
• Selective Methylation of Arenes: A Radical C−H Functionalization/Cross‐Coupling Sequence
  作者：Fabien Serpier、Fei Pan、Won Seok Ham、Jérôme Jacq、Christophe Genicot、Tobias Ritter

  DOI：10.1002/anie.201804628

  日期：2018.8.13

  A selective, nonchelation‐assisted methylation of arenes has been developed. The overall transformation, which combines a C−H functionalization reaction with a nickel‐catalyzed cross‐coupling, offers rapid access to methylated arenes with high para selectivity. The reaction is amenable to late‐stage methylation of small‐molecule pharmaceuticals.

  已经开发出一种选择性的，非螯合辅助的芳烃甲基化方法。整体转化结合了CH官能化反应和镍催化的交叉偶联，可快速获得具有高对位选择性的甲基化芳烃。该反应适合小分子药物的后期甲基化。
• Palladium-catalysed electrophilic aromatic C–H fluorination
  作者：Kumiko Yamamoto、Jiakun Li、Jeffrey A. O. Garber、Julian D. Rolfes、Gregory B. Boursalian、Jannik C. Borghs、Christophe Genicot、Jérôme Jacq、Maurice van Gastel、Frank Neese、Tobias Ritter

  DOI：10.1038/nature25749

  日期：2018.2

  such as increased metabolic stability or better blood–brain-barrier penetration, may become available. Here we describe an approach to catalysis and the resulting development of an undirected, palladium-catalysed method for aromatic C–H fluorination using mild electrophilic fluorinating reagents. The reaction involves a mode of catalysis that is unusual in aromatic C–H functionalization because no organometallic

  芳基氟广泛用于制药和农业化学工业，最近的进展使它们能够通过各种官能团的转化来合成。然而，缺乏用于直接芳族碳氢（C-H）氟化的通用方法。传统方法需要使用强氟化试剂，这通常是非选择性且难以处理的，例如元素氟，或者仅攻击活性最强的芳烃的反应性较低的试剂，这会缩小底物范围。一种直接氟化芳族 C-H 键的方法可以促进获得功能分子的氟化衍生物，否则这些衍生物将难以生产。例如，具有改进特性的候选药物，例如增加代谢稳定性或更好的血脑屏障渗透，可能会变得可用。在这里，我们描述了一种催化方法以及使用温和的亲电子氟化试剂进行芳族 C-H 氟化的非定向钯催化方法的开发。该反应涉及一种在芳香族 C-H 官能化中不常见的催化模式，因为没有形成有机金属中间体；相反，通过催化生成反应性过渡金属氟化物亲电试剂，用于芳烃的氟化，否则这些芳烃不会与温和的氟化试剂反应。该反应的范围和官能团耐受性可以提供在药物和农用化学品开发中获
• Irani, Current Science, 1945, vol. 14, p. 327
  作者：Irani

  DOI：——

  日期：——
• 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.