N-(3,5-dichlorophenyl)-4-methylbenzenesulfonamide

• 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-dichlorophenyl)-4-methylbenzenesulfonamide
• 英文别名: toluene-4-sulfonic acid-(3,5-dichloro-anilide)；Toluol-4-sulfonsaeure-(3,5-dichlor-anilid)
• 化学式: C₁₃H₁₁Cl₂NO₂S
• 分子量: 316.208
• InChiKey: AARIBYDYSSRQAV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 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：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,5-dichlorophenyl)-4-methylbenzenesulfonamide 在 iron(III) chloride 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 30.0h， 生成 1,3-dichloro-7-phenyl-5-tosyl-6,7-dihydro-5H-indeno[2,1-c]quinoline
  参考文献：
  名称：

  Iron-Mediated Carboarylation/Cyclization of Propargylanilines with Acetals: A Concise Route to Indeno[2,1-c]quinolines

  摘要：

  FeCl3- and FeBr3-mediated tandem carboarylation/cyclization of propargylanilines with diethyl benzaldehyde acetals furnished the tetracyclic core of indeno[2,1-c]quinolines. 5-Tosyl-6,7-dihydro-5H-indeno[2,1-c]quinoline and 7H-indeno[2,1-c]quinoline derivatives were obtained in good to excellent yields, respectively, by tuning the FeX3 loadings and/or reaction temperatures.

  DOI：

  10.1021/ol503039j
• 作为产物：
  描述：

  2,4-dichloro-6-[(4-methylphenyl)sulfonamido]benzoic acid 在 palladium diacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.0h， 生成 N-(3,5-dichlorophenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  直接C ？苯甲酸的H酰胺化通过串联脱羧引入间氨基和对氨基

  摘要：

  开发了具有磺酰叠氮化物的苯甲酸的Ir催化轻度CH酰胺化反应，可实现高效且具有官能团相容性的反应。随后，将氨基酰胺化的邻氨基苯甲酸产物进行原羧化反应，可得到间位或对位取代的（N-磺酰基）苯胺衍生物，而其他CH官能化方法则无法获得后者。脱羧步骤与酰胺化条件兼容，可实现方便的一锅两步工艺。

  DOI：

  10.1002/chem.201500331

文献信息

• Copper-Mediated C–N Coupling of Arylsilanes with Nitrogen Nucleophiles
  作者：Johannes Morstein、Eric D. Kalkman、Chen Cheng、John F. Hartwig

  DOI：10.1021/acs.orglett.6b02543

  日期：2016.10.21

  A method for the oxidative coupling of arylsilanes with nitrogen nucleophiles is reported. This method occurs with a broad range of heptamethyltrisiloxylarenes and nitrogen nucleophiles, proceeds with the arylsilane as limiting reagent, and does not require a fluoride activator with electron-poor arylsilanes. The combination of this method with C–H silylation generates arylamines from unactivated arenes

  报道了芳基硅烷与氮亲核试剂的氧化偶联的方法。该方法可与多种七甲基三甲硅烷氧基芳烃和氮亲核试剂一起使用，并以芳基硅烷作为限制试剂进行，并且不需要具有电子贫乏的芳基硅烷的氟化物活化剂。该方法与C–H甲硅烷基化相结合，可从未活化的芳烃中生成芳胺，其位点选择性受空间效应控制。通过这些步骤的组合，可以直接访问许多无法通过替代的C–H功能化方法访问的化合物，包括直接的C–H胺化或C–H硼化和胺化的组合。
• Synthesis of N-Arylsulfonamides by a Copper-Catalyzed Reaction of Chloramine-T and Arylboronic Acids at Room Temperature
  作者：Banlai Ouyang、Guanyinsheng Qiu、Deming Liu、Kejian Xia、Yanxia Zheng、Hongxin Mei

  DOI：10.1055/s-0036-1590978

  日期：2018.1

  A copper-catalyzed Chan–Lam-coupling-like reaction of a (het)arylboronic acid and chloramine-T (or a related compound) has been developed for the synthesis of N -arylsulfonamides at room temperature in moderate to good yields, with good tolerance of functional groups. In this process, it is believed that chloramine-T serves as an electrophile.

  已经开发了一种铜催化的（杂）芳基硼酸和氯胺-T（或相关化合物）的 Chan-Lam 偶联反应，用于在室温下以中等至良好的收率合成 N-芳基磺酰胺，并具有良好的官能团的耐受性。在此过程中，据信氯胺-T 用作亲电子试剂。
• Copper-catalyzed cross-coupling of chloramine salts and arylboronic acids in water: A green and practical route to N-arylsulfonamides
  作者：Banlai Ouyang、Yanxia Zheng、Yi Liu、Fei Liu、Juying Yao、Yiyuan Peng

  DOI：10.1016/j.tetlet.2018.09.001

  日期：2018.10

  A green and practical method for the synthesis of N-arylsulfonamides from chloramine salts and arylboronic acids is herein developed. The reaction proceeds readily in the presence of 5 mol% of CuI and 2.5 equiv. K2CO3 in water at room temperature, generating a variety of N-arylsulfonamides in moderate to good yields with good functional group tolerance.

  本文开发了一种从氯胺盐和芳基硼酸合成N-芳基磺酰胺的绿色实用方法。在5mol％的CuI和2.5当量的存在下，反应容易进行。室温下水中的K 2 CO 3，以中等至良好的产率生成各种N-芳基磺酰胺，并具有良好的官能团耐受性。
• Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)2–H Coupling
  作者：Zhipeng Liang、Ya-Nan Wu、Yang Wang

  DOI：10.3390/molecules27175539

  日期：——

  phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the nitrogen nucleophilic substitution reactions. Significantly, this transformation intends to utilize the property of visible light-induced azides to generate triplet

  我们通过双铜和可见光催化开发了苯基亚磺酸衍生物和芳基叠氮化物之间的S(O) 2 –N偶联。在这种高效且温和的途径中，反应在氧化还原中性条件下产生磺酰胺化合物，这在机制上不同于氮亲核取代反应。值得注意的是，这种转化旨在利用可见光诱导叠氮化物的性质生成三线态氮宾，然后与磺酰基自由基原位偶联，以良好的产率获得结构多样的苯亚磺酰胺。
• Design and synthesis of benzenesulfonanilides active against methicillin-resistant Staphylococcus aureus and vancomycin-resistant Enterococcus
  作者：Kensuke Namba、Xiaoxia Zheng、Kazunori Motoshima、Hidetomo Kobayashi、Akihiro Tai、Eizo Takahashi、Kenji Sasaki、Keinosuke Okamoto、Hiroki Kakuta

  DOI：10.1016/j.bmc.2008.04.040

  日期：2008.6

  Vancomycin is mainly used as an antibacterial agent of last resort, but recently vancomycin-resistant bacterial strains have been emerging. Although new antimicrobials have been developed in order to overcome drug-resistant bacteria, many are structurally complex beta-lactams or quinolones. In this study, we aimed to create new anti-drug-resistance antibacterials which can be synthesized in a few steps from inexpensive starting materials. Since sulfa drugs function as p-aminobenzoic acid mimics and inhibit dihydropteroate synthase (DHPS) in the folate pathway, we hypothesized that sulfa derivatives would act as folate metabolite-mimics and inhibit bacterial folate metabolism. Screening of our sulfonanilide libraries, including benzenesulfonanilide-type cyclooxygenase-1-selective inhibitors, led us to discover benzenesulfonanilides with potent anti-methicillin-resistant Staphylococcus aureus (MRSA)/vancomycin-resistant Enterococcus (VRE) activity, that is, N-3,5-bis(trifluoromethyl) phenyl-3,5-dichlorobenzenesulfonanilide (16b) [MIC = 0.5 mu g/mL (MRSA), 1.0 mu g/mL (VRE)], and 3,5-bis(trifluoromethyl)-N-(3,5-dichlorophenyl) benzenesulfonanilide (16c) [MIC = 0.5 mu g/mL (MRSA), 1.0 mu g/mL (VRE)]. These compounds are more active than vancomycin [MIC = 2.0 mu g/mL (MRSA), 125 mu g/mL (VRE)], but do not possess an amino group, which is essential for DHPS inhibition by sulfa drugs. These results suggested that the mechanism of antibacterial action of compounds 16b and 16c is different from that of sulfa drugs. We also confirmed the activity of these compounds against clinical isolates of Gram-positive bacteria. (C) 2008 Elsevier Ltd. All rights reserved.