4'-iodo-4-nitrobenzenesulfonanilide | 332025-19-1

• 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'-iodo-4-nitrobenzenesulfonanilide
• 英文别名: N-(4'-nitrophenylsulfonyl)-4-iodoaniline；N-(4-iodophenyl)-4-nitrobenzenesulfonamide
• CAS: 332025-19-1
• 化学式: C₁₂H₉IN₂O₄S
• mdl: MFCD00422242
• 分子量: 404.185
• InChiKey: PBZMAUSOHKHKAD-UHFFFAOYSA-N

物化性质

• 熔点：
  234.5-236 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  512.5±60.0 °C(Predicted)
• 密度：
  1.902±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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'-iodo-4-nitrobenzenesulfonanilide 在 盐酸 、 tin 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 4-amino-N-(4-iodophenyl)-N-methylbenzenesulfonamide
  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 、 对碘苯胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 4'-iodo-4-nitrobenzenesulfonanilide
  参考文献：
  名称：

  烯烃的电化学邻二氟氟化：可扩展且适合于富含电子的底物。

  摘要：

  氟化烷基是生物活性化合物中的重要基序，对药代动力学，效能和构象有积极影响。烯烃的氧化二氟化代表了其制备的重要策略，但是目前的方法在其烯烃类型和对富电子，易氧化的官能团的耐受性以及其安全性和可扩展性方面受到限制。在此，我们报告了一种可耐受多种富电子功能的未活化烯烃类型二氟化的方法，可得到原本无法获得的产物。成功的关键是使用“细胞外”方法电化学生成高价碘介体，该方法可避免氧化性底物分解。可持续性更高的条件可在高达十亿磅的范围内带来出色的产量。

  DOI：

  10.1002/anie.201912119

文献信息

• 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。
• Palladium-Catalyzed Enantioselective 1,1-Fluoroarylation of Aminoalkenes
  作者：Ying He、Zhenyu Yang、Richard T. Thornbury、F. Dean Toste

  DOI：10.1021/jacs.5b07795

  日期：2015.9.30

  The development of an enantioselective palladium-catalyzed 1,1-fluoroarylation of unactivated aminoalkenes is described. The reaction uses arylboronic acids as the arene source and Selectfluor as the fluorine source to generate benzylic fluorides in good yields with excellent enantioselectivities. This transformation, likely proceeding through an oxidative Heck mechanism, affords 1,1-difunctionalized

  描述了未活化氨基烯烃的对映选择性钯催化 1,1-氟芳基化的开发。该反应使用芳基硼酸作为芳烃源，Selectfluor 作为氟源，以良好的收率和优异的对映选择性生成苄基氟化物。这种转化可能通过氧化 Heck 机制进行，提供 1,1-双官能化烯烃产物。
• Metal-Free β-Amino Alcohol Synthesis: A Two-step Smiles Rearrangement
  作者：Di Yang、Cai-Xia Xie、Xiao-Tian Wu、Luo-Ran Fei、Lei Feng、Chen Ma

  DOI：10.1021/acs.joc.0c01543

  日期：2020.12.4

  A novel method for the synthesis of β-amino alcohols has been demonstrated under mild reaction conditions with a broad scope via a two-step Smiles rearrangement. What is more, theoretical calculations have been performed to confirm the rationality of the mechanism. The method has been proved to be notably effective for N-arylated amino alcohols, which are difficult to synthesize by traditional methods

  通过两步Smiles重排，在温和的反应条件下，已证明了在宽泛范围内合成β-氨基醇的新方法。此外，已经进行了理论计算以确认该机制的合理性。已经证明该方法对于N-芳基化的氨基醇特别有效，N-芳基化的氨基醇难以通过传统方法合成。
• Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions
  作者：Craig J. Kelly、Janet M. S. Skakle、James L. Wardell、Solange M. S. V. Wardell、John N. Low、Christopher Glidewell

  DOI：10.1107/s0108768101016858

  日期：2002.2.1

  together generate a chain of fused rings: the combination of a C-H...O hydrogen bond and aromatic pi...pi stacking interactions links the chains into sheets. Molecules of N-(4'-iodophenylsulfonyl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO2C6H4I-4' (5), are linked by N-H...O=S and C-H...O(nitro) hydrogen bonds into a chain containing alternating R2(2)(8) and R2(2)(10) rings, but there are no I..

  N-（4'-碘苯基磺酰基）-4-硝基苯胺的分子4-O2NC6H4NHSO2C6H4I-4'（1）通过三中心I ... O2N相互作用连接成链，这些链被连接成三维框架通过CH ... O氢键 在同分异构的N-（4'-硝基苯磺酰基）-4-碘苯胺4-IC6H4NHSO2C6H4NO2-4'（2）中，由I ... O2N相互作用产生的链又通过CH连接成三维构架。 .O氢键。N，N-双（3'-硝基苯基磺酰基）-4-碘苯胺，4-IC6H4N（SO2C6H4NO（2）-3'）2（3）的分子位于空间组C2 / c的两倍旋转轴上并且彼此相连通过成对的IO = S相互作用形成链：这些链通过CH ... O氢键连接成片，而片通过芳族PI ...堆积相互作用连接成三维骨架。在N-（4' -碘苯基磺酰基）-3-硝基苯胺，3-O2NC6H4NHSO2C6H4I-4'（4），有由硬NH ... O = S氢键形成的R2
• Traceless N‐Polyfluoroalkylation of Weakly Nucleophilic Nitrogen Containing Compounds
  作者：Laura Santos、Florian Audet、Morgan Donnard、Armen Panossian、Jean-Pierre Vors、David Bernier、Sergii Pazenok、Frederic R. Leroux

  DOI：10.1002/chem.202300792

  日期：——

  the high cost, toxicity or environmental impact of commonly used polyfluoroalkylation reagents. We report the sulfuryl fluoride (SO2F2)-mediated N-polyfluoroalkylation of weakly nucleophilic nitrogen compounds from readily available fluorinated alcohols. This method opens access to a variety of N-polyfluoroalkylated building blocks that are highly valuable for life science applications.

  由于常用多氟烷基化试剂的高成本、毒性或环境影响， N-多氟烷基化反应具有挑战性。我们报告了硫酰氟 (SO 2 F 2 ) 介导的弱亲核氮化合物的N -多氟烷基化，这些化合物来自现成的氟化醇。该方法开启了对各种N-多氟烷基化构建块的访问，这些构建块对生命科学应用具有很高的价值。