4-nitro-N-(p-tolyl)benzenesulfonamide | 109845-76-3

• 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-nitro-N-(p-tolyl)benzenesulfonamide
• 英文别名: Benzenesulfonamide, N-(4-methylphenyl)-4-nitro-；N-(4-methylphenyl)-4-nitrobenzenesulfonamide
• CAS: 109845-76-3
• 化学式: C₁₃H₁₂N₂O₄S
• 分子量: 292.315
• InChiKey: AFKDMQMBJADFHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  4-nitro-N-(p-tolyl)benzenesulfonamide 在 palladium 10% on activated carbon 氢气 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以88%的产率得到4-氨基-N-(4-甲基苯基)苯磺酰胺
  参考文献：
  名称：

  WO2008/55233

  摘要：

  公开号：
• 作为产物：
  描述：

  对甲酚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 caesium carbonate 、 2-二-叔丁膦基-2',4',6'-三异丙基联苯 作用下， 以 2-甲基-2-丁醇 、 乙腈 为溶剂， 反应 22.0h， 生成 4-nitro-N-(p-tolyl)benzenesulfonamide
  参考文献：
  名称：

  A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

  摘要：

  A general method for Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates (aryl nonaflates) is described. A biaryl phosphine ligand, t-BuXPhos, formed the most active catalyst, and K3PO4 in tert-amyl alcohol was found to be the optimal base solvent combination for the reaction. The reaction conditions were tolerant of various functional groups such as cyano, nitro, ester, aldehyde, ketone, chloride, carbamate, and phenol. Heterocyclic aryl nonaflates were found to be suitable coupling partners. High yields of the coupled products were obtained from the reactions between inherently disfavored substrates such as electron-rich nonaflates and electron-poor sulfonamides. Kinetic data suggest reductive elimination to be the rate-limiting step for the reaction. The only limitation of this methodology that we have identified is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

  DOI：

  10.1021/jo200443u

文献信息

• A highly efficient heterogeneous copper-catalyzed Chan–Lam coupling reaction of sulfonyl azides with arylboronic acids leading to N-arylsulfonamides
  作者：Chongren You、Fang Yao、Tao Yan、Mingzhong Cai

  DOI：10.1039/c6ra04298h

  日期：——

  A heterogeneous Chan–Lam coupling reaction between sulfonyl azides and arylboronic acids was achieved in MeOH at room temperature in the presence of 10 mol% of an L-proline-functionalized MCM-41-immobilized copper(I) complex [MCM-41–L-proline–CuCl] under air, yielding a variety of N-arylsulfonamides in excellent yields. The new heterogeneous copper complex can be prepared from commercially readily

  在室温下，在存在10 mol％的L-脯氨酸官能化的MCM-41固定化铜（I）络合物[MCM-41– L]的情况下，在MeOH中实现了磺酰叠氮化物与芳基硼酸之间的异质Chan-Lam偶联反应-脯氨酸–CuCl ]在空气中产生多种N-芳基磺酰胺，收率极高。新的多相铜络合物可以由市售的廉价试剂制备，并通过简单过滤反应溶液进行回收，并循环至少8次而不会降低活性。
• Ligand-Enabled Gold-Catalyzed C(sp²)–N Cross-Coupling Reactions of Aryl Iodides with Amines
  作者：Manjur O. Akram、Avishek Das、Indradweep Chakrabarty、Nitin T. Patil

  DOI：10.1021/acs.orglett.9b03082

  日期：2019.10.4

  example of ancillary (P,N)-ligand-enabled gold-catalyzed C-N cross-coupling reactions of aryl iodides with amines is reported. The high generality of the reaction in de novo synthesis, late-stage modifications, and cascade processes to access functionalized indolinones and carbazoles underscores the synthetic potential of the presented strategy. Monitoring the reaction with ESI-HRMS and NMR provided strong

  报道了芳基碘化物与胺的辅助（P，N）-配体使能的金催化的CN交叉偶联反应的第一个例子。在从头合成，后期修饰和级联过程中获得官能化的吲哚酮和咔唑的反应具有很高的通用性，这突出了所提出策略的合成潜力。用ESI-HRMS和NMR监测反应为原位形成假定的高价Au（III）中间体提供了有力的证据。
• Arylation and alkenylation of activated alkyl halides using sulfonamides
  作者：Stuart Johnson、Ervin Kovács、Michael F. Greaney

  DOI：10.1039/d0cc00220h

  日期：——

  of quaternary aryl amino acid derivatives can be synthesised using tandem SN2/Smiles rearrangement chemistry involving aryl sulfonamides and α-chloro carbonyl compounds. The reaction harnesses a sulfur dioxide extrusion pathway to construct a C-N and C-Caryl bond under simple conditions with no requirement for organometallics or transition metal catalysts. The reaction is also successful for alkenyl

  可以使用涉及芳基磺酰胺和α-氯羰基化合物的串联SN2 / Smiles重排化学方法合成各种季芳基氨基酸衍生物。该反应利用二氧化硫挤出途径在简单条件下构建CN和C-C芳基键，而无需有机金属或过渡金属催化剂。对于烯基磺酰胺，该反应也是成功的，产生空间上拥挤的季烯氨基酸衍生物。
• A Cascade Reaction of Michael Addition and Truce-Smiles Rearrangement to Synthesize Trisubstituted 4-Quinolone Derivatives
  作者：Caixia Xie、Di Yang、Xinfeng Wang、Chen Ma

  DOI：10.1021/acs.joc.0c01662

  日期：2020.12.4

  A novel transition-metal-free cascade reaction to synthesize 4-quinolone derivatives has been demonstrated. Michael addition and Truce-Smiles rearrangement are included in this protocol, providing a broad scope of 4-quinolones in moderate-to-excellent yields. This work serves as an example of the use of sulfonamides through Truce–Smiles rearrangement to build heterocyclic compounds under mild conditions

  一种新型的无过渡金属的级联反应已被证明可以合成4-喹诺酮衍生物。该方案包括迈克尔加成和Truce-Smiles重排，以中等至优异的产率提供了广泛的4-喹诺酮类药物。这项工作作为通过Truce-Smiles重排使用磺酰胺在温和条件下构建杂环化合物的一个例子。
• 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。