N-(2,3-dimethylphenyl)-4-methylbenzenesulfonamide | 54027-45-1

• 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: N-(2,3-dimethylphenyl)-4-methylbenzenesulfonamide
• 英文别名: 2,3-dimethyl-N-tosylbenzenamine；toluene-4-sulfonic acid-(2,3-dimethyl-anilide)；Toluol-4-sulfonsaeure-(2,3-dimethyl-anilid)
• CAS: 54027-45-1
• 化学式: C₁₅H₁₇NO₂S
• mdl: MFCD00684368
• 分子量: 275.371
• InChiKey: NPHSDBOKJYJHBH-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C(Solv: ethanol (64-17-5))
• 沸点：
  413.1±55.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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-(2,3-dimethylphenyl)-4-methylbenzenesulfonamide 在 磺酰氯 作用下， 生成 toluene-4-sulfonic acid-(4-anilino-2,3-dichloro-5,6-dimethyl-anilide)
  参考文献：
  名称：

  作为取代过程中可能的中间体的添加剂化合物。第二部分

  摘要：

  DOI：

  10.1039/jr9550002376
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 为溶剂， 生成 N-(2,3-dimethylphenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Abbasi, Muhammad Athar; Sheeza, Anam; Aziz-Ur-Rehman, Journal of the Chemical Society of Pakistan, 2015, vol. 37, # 3, p. 541 - 548

  摘要：

  DOI：

文献信息

• Utilization of transition metal fluoride-based solid support catalysts for the synthesis of sulfonamides: carbonic anhydrase inhibitory activity and <i>in silico</i> study
  作者：Deedar Ali、Sayyeda Tayyeba Amjad、Zainab Shafique、Muhammad Moazzam Naseer、Mariya al-Rashida、Tayyaba Allamgir Sindhu、Shafia Iftikhar、Muhammad Raza Shah、Abdul Hameed、Jamshed Iqbal

  DOI：10.1039/d1ra07844e

  日期：——

  The applications of solid support catalysts in catalyzing organic reactions are well-evident. In the present study, we explored a transition metal fluoride (FeF3) adsorbed on molecular sieves (4 Å) as a solid support catalyst for the preparation of sulfonamides 3a–3o. The solid support catalyst was characterized via X-ray diffraction and AFM analysis. The catalyst was further explored for the synthesis

  固体载体催化剂在催化有机反应中的应用是显而易见的。在本研究中，我们探索了一种吸附在分子筛（4 Å）上的过渡金属氟化物（FeF 3 ）作为制备磺胺类药物3a-3o的固体载体催化剂。通过X 射线衍射和 AFM 分析对固体载体催化剂进行了表征。进一步探索了该催化剂用于合成吲哚6a-h、1H-四唑和 1,4-二氢吡啶。研究了本文制备的磺胺类药物抑制碳酸酐酶（hCA II、hCA IX 和 hCA XII）的潜力。发现所有化合物都是具有 IC 50的活性抑制剂在低微摩尔范围内的值。有些化合物甚至被发现是高度选择性的抑制剂。化合物3i仅抑制 hCA II (IC 50 = 2.76 ± 1.1 μM) 并且对 hCA IX 和 hCA XII 具有 <27% 的抑制作用。类似地，3e (IC 50 = 0.63 ± 0.14 μM) 仅抑制 hCA XII，对 hCA II 和 hCA IX 的抑制
• Electrochemical C–H Mono-/Multi-Bromination Regulation of <i>N</i>-Sulfonylanilines on a Cost-Effective Carbon Fiber Electrode and Its Prospective Electroactive Molecule Screening
  作者：Shuchun Xie、Li Fu、Yechun Ding、Qi Wang、Chen He、Wenjun Xu、Qing Wang、Yingfang Zhong、Xiaona Fan、Min Yang

  DOI：10.1021/acs.joc.4c00080

  日期：——

  conditions with a broad substrate scope, affording diverse mono/multi-brominated anilines in moderate to good yields. Mechanism study reveals that this transformation involves anodic oxidation, aromatic electrophilic substitution, and deprotonation. Preliminary electroactive molecule screening results in its prospective application in electroactive MBs for electrochemical biosensors.

  描述了在经济有效的 CF 电极上N-磺酰基苯胺的电化学 C-H 单/多溴化调节。该反应在温和条件下顺利进行，底物范围广泛，以中等至良好的产率提供多种单/多溴苯胺。机理研究表明，这种转变涉及阳极氧化、芳香亲电取代和去质子化。初步的电活性分子筛选结果表明其在电化学生物传感器的电活性MB中的应用前景。
• Transition-metal-free direct amination of simple arenes with sulfonyl azides
  作者：Lianggui Wang、Arun Jyoti Borah、Guobing Yan

  DOI：10.1016/j.tetlet.2015.02.009

  日期：2015.3

  A metal-free green protocol has been developed for amination of simple arenes using arylsulfonyl azides via a nitrene transfer process under solvent free conditions at 130 degrees C releasing N-2 gas as the sole by-product. (C) 2015 Elsevier Ltd. All rights reserved.
• Identification of novel glycine sulfonamide antagonists for the EP1 receptor
  作者：Stephen C. McKeown、Adrian Hall、Richard Blunt、Susan H. Brown、Iain P. Chessell、Anita Chowdhury、Gerard M.P. Giblin、Mark P. Healy、Matthew R. Johnson、Olivier Lorthioir、Anton D. Michel、Alan Naylor、Xiao Lewell、Shilina Roman、Stephen P. Watson、Wendy J. Winchester、Richard J. Wilson

  DOI：10.1016/j.bmcl.2006.12.060

  日期：2007.3

  A high-throughput screen targeting the EP1 receptor identified non-acidic glycine sulfonarnide derivative 2a with a pKi of 6.2. Analogue synthesis allowed a thorough investigation of the structure-activity relationship (SAR) and led to a 100-fold increase in recombinant potency. (c) 2006 Elsevier Ltd. All rights reserved.
• Half-Sandwich Scorpionates as Nitrene Transfer Catalysts
  作者：Shengwen Liang、Michael P. Jensen

  DOI：10.1021/om3009102

  日期：2012.12.10

  Scorpionate complexes of the middle to late 3d transition metals [(L)M(NCMe)(3)](BF4)(n) (M = Mn, Fe, Co, Ni: 1(M), L = tris(3,5-dimethylpyrazol-1-yl)methane, Tpm(Me,Me), n = 2; 2(M), L = tris(3-phenylpyrazol-1-yl)methane, Tpm(Ph), n = 2; 3(M) except 3(Mn), L = hydrotris(3,5-dimethylpyrazol-1-yl)borate, [Tp(Me,Me)](-), n = 1; 4(M), L = hydrotris(3-phenyl-5-methylpyrazol-1-yl)borate, [Tp(Ph,Me)](-), n = 1) were examined as catalysts for styrene aziridination and THF amination using phenyl-N-tosyliodinane as a nitrene donor. [(Tpm(Me,Me))Fe(NCMe)(3)](BF4)(2) (1(Fe)) was identified as the most active catalyst, giving nearly quantitative nitrene transfer yields at 5 mol % loadings. The reactivity of 1(Fe) with a wider range of organic substrates was also explored, and a striking observation was strong selectivity for aromatic rather than benzylic amination for alkylaromatic substrates.