3-chloro-N-(p-tolyl)benzenesulfonamide | 16964-20-8

• 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: 3-chloro-N-(p-tolyl)benzenesulfonamide
• 英文别名: 3-chloro-N-(4-methylphenyl)benzenesulfonamide
• CAS: 16964-20-8
• 化学式: C₁₃H₁₂ClNO₂S
• 分子量: 281.763
• InChiKey: NZMWVYQPRZLTOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 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：

  3-chloro-N-(p-tolyl)benzenesulfonamide 、 N,N-二乙基-2-氯乙酰胺 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(3-chloro-benzenesulfonyl)-p-tolyl-amino]-N,N-diethyl-acetamide
  参考文献：
  名称：

  N-Glycine-sulfonamides as potent dual orexin 1/orexin 2 receptor antagonists

  摘要：

  A series of dual OX(1)R/OX(2)R orexin antagonists was prepared based on a N-glycine-sulfonamide core. SAR studies of a screening hit led to compounds with low nanomolar affinity for both receptors and good oral bioavailability. One of these compounds, 47, has demonstrated in vivo activity in rats following oral administration. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.079
• 作为产物：
  描述：

  4-硝基甲苯 、 3-氯苯硼酸 在 1,10-菲罗啉 、 tetrakis(actonitrile)copper(I) hexafluorophosphate 、 potassium pyrosulfite 、 异丙醇 作用下， 反应 48.0h， 以80%的产率得到3-chloro-N-(p-tolyl)benzenesulfonamide
  参考文献：
  名称：

  铜催化通过插入二氧化硫从硝基芳烃合成磺酰胺。

  摘要：

  硝基芳烃通过插入二氧化硫用作磺酰胺的偶联伙伴。在铜催化下，芳基硼酸，硝基芳烃和偏亚硫酸氢钾的三组分反应平稳进行，从而产生了一系列磺酰胺类化合物，具有良好的收率和优异的收率，具有广泛的底物范围。包括羟基，氰基，氨基和羰基在内的各种官能团都是可以耐受的。提出了一个合理的机理，表明芳基亚磺酸盐是中间体，硝基芳烃和芳基亚磺酸盐的铜辅助相互作用是关键步骤。该方法还扩展到当前市售药物（氟他胺）的后期修饰。

  DOI：

  10.1039/d0cc00721h

文献信息

• Development of <i>N</i>-(4-Phenoxyphenyl)benzenesulfonamide Derivatives as Novel Nonsteroidal Progesterone Receptor Antagonists
  作者：Ayumi Yamada、Yuko Kazui、Hiromasa Yoshioka、Aya Tanatani、Shuichi Mori、Hiroyuki Kagechika、Shinya Fujii

  DOI：10.1021/acsmedchemlett.6b00184

  日期：2016.12.8

  we adopted 3-chlorobenzenesulfonyl derivative 20a as a lead compound for structural development. Among the synthesized compounds, 3-trifluoromethyl derivative 32 exhibited the most potent PR-antagonistic activity, with high binding affinity for PR and selectivity over androgen receptor (AR). It is structurally distinct from other nonsteroidal PR antagonists, including cyanopyrrole derivatives, and

  我们在这里报告的N-（4-苯氧基苯基）苯磺酰胺衍生物作为一类新型的非甾体孕酮受体（PR）拮抗剂的发展。PR在包括女性生殖系统在内的各种生理系统中起着关键作用，PR拮抗剂是临床治疗多种疾病的候选药物，包括子宫平滑肌瘤，子宫内膜异位症，乳腺癌和某些精神疾病。我们发现苯磺酰苯胺骨架作为PR拮抗剂的新型支架，我们采用3-氯苯磺酰衍生物20a作为结构开发的先导化合物。在合成的化合物中，3-三氟甲基衍生物32表现出最有效的PR拮抗活性，对PR具有高结合亲和力，并且相对于雄激素受体（AR）具有选择性。
• Nitrosoarenes as Nitrogen Source for Generation of Sulfonamides with the Insertion of Sulfur Dioxide under <scp>Metal‐Free</scp> Conditions ^†
  作者：Xuefeng Wang、Yanmei Lin、Jin‐Biao Liu、Fu‐Sheng He、Yunyan Kuang、Jie Wu

  DOI：10.1002/cjoc.202000053

  日期：2020.10

  A metal‐free reaction of nitrosoarenes, aryldiazonium tetrafluoroborates, and sulfur dioxide under mild conditions is developed, giving rise to sulfonamides in moderate to good yields. This transformation proceeds efficiently at room temperature in the presence of cyclohexa‐1,4‐diene with a broad reaction scope. Good functional group compatibility is observed, including cyano, halo, and ester. A plausible

  在温和条件下开发了亚硝基芳烃，芳基重氮四氟硼酸盐和二氧化硫的无金属反应，从而以中等至良好的产率产生了磺酰胺。在具有宽反应范围的环己-1,4-二烯存在下，这种转化在室温下可有效进行。观察到良好的官能团相容性，包括氰基，卤素和酯。提出了一种可能的机制，其中涉及一个自由基过程，其中插入了二氧化硫，并且在转化过程中，环己-1,4-二烯用作还原剂。
• Polymorphism in Secondary Benzene Sulfonamides
  作者：Palash Sanphui、Bipul Sarma、Ashwini Nangia

  DOI：10.1021/cg100845f

  日期：2010.10.6

  The role of about 20 different solvents in the crystallization of polymorphs for 13 N-phenyl benzene sulfonamides was studied. Five compounds (1, 2, 3, 7, and 11) are dimorphic, and one is trimorphic (6). All the crystalline solids were characterized by powder and single crystal X-ray diffraction, thermal analysis, hot stage microscopy, and IR and Raman spectroscopy. The phase transition from a metastable form to the stable form was examined visually for two compounds (1, 11) on a HSM and confirmed by differential scanning calorimetry and X-ray diffraction. The N-H center dot center dot center dot O hydrogen bond catemer (chain) and dimer (cyclic) motifs of the sulfonamide group were analyzed as the main difference between polymorphs of 1, 3, and 6. Weaker C-H center dot center dot center dot O interactions differentiate the molecular packing of other polymorphic systems. Accordingly, these crystal structures are referred to as synthon polymorphs. The occurrence of N-H center dot center dot center dot O catemer and dimer synthon in secondary sulfonamides is compared with crystal structures in the Cambridge database. The nearly equal probability of the dimer and catemer motifs for secondary sulfonamides (similar to 19%) is attributed to the possibility of making the catemer synthon via both anti and syn oxygen atoms of the SO(2)NH group, with the former acceptor being preferred in two-thirds of the cases.