N-benzhydryl-4-methoxybenzenesulfonamide | 346692-15-7

• 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-benzhydryl-4-methoxybenzenesulfonamide
• CAS: 346692-15-7
• 化学式: C₂₀H₁₉NO₃S
• 分子量: 353.442
• InChiKey: NSOXOHVAAHBFMV-UHFFFAOYSA-N

物化性质

• 沸点：
  526.6±60.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  二苯基甲烷 、 对甲氧基苯磺酰胺 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 硝基甲烷 为溶剂， 反应 4.0h， 以87%的产率得到N-benzhydryl-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  DDQ-mediated direct oxidative coupling of amides with benzylic and allylic sp3 C–H bonds under metal-free conditions

  摘要：

  A simple and efficient method for the direct oxidative coupling of amides with benzylic and allylic sp(3) C-H bonds using DDQ as an oxidant is described. A range of amides including benzamide, benzyl carbamate, and substituted sulfonamides reacted efficiently with various benzylic and allylic substrates under metal free conditions to afford amidation products in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.03.137

文献信息

• Selective catalytic Hofmann N-alkylation of poor nucleophilic amines and amides with catalytic amounts of alkyl halides
  作者：Qing Xu、Huamei Xie、Er-Lei Zhang、Xiantao Ma、Jianhui Chen、Xiao-Chun Yu、Huan Li

  DOI：10.1039/c6gc00938g

  日期：——

  A selective Hofmann N-alkylation reaction of amines/amides catalytic in alkyl halides is achieved by using alcohols as the alkylating reagents, affording mono- or di-alkylated amines/amides in high selectivities.

  通过使用醇作为烷基化试剂，实现烷基卤化物中催化的胺/酰胺的霍夫曼N-烷基的选择性霍夫曼N-烷基化反应，从而以高选择性提供单或二烷基化的胺/酰胺。
• Reaction Route and Mechanism of the Direct N-Alkylation of Sulfonamides on Acidic Mesoporous Zeolite β-Catalyst
  作者：Wenqian Fu、Runsheng Shen、Enhui Bai、Lei Zhang、Qun Chen、Zhongxue Fang、Guangchao Li、Xianfeng Yi、Anmin Zheng、Tiandi Tang

  DOI：10.1021/acscatal.8b02030

  日期：2018.10.5

  of sulfonamides with alcohols. The strongly acidic HBeta-M had a higher intrinsic activity with initial turnover frequency of 11 × 10–2 s–1 than those of H-form mordenite nanosheets (3.3 × 10–2 s–1) and montmorillonite (4.0 × 10–2 s–1) catalysts. The experiment and characterization results demonstrate that there are two parallel reaction routes on the acidic catalysts. One route is the reaction of

  具有强酸性和中孔结构的高活性多相催化剂的开发是有机合成的极具吸引力的策略。在这项研究中，合成了具有大粒径和强酸性的介孔沸石β（HBeta-M），并将其用于磺酰胺与醇的直接N-烷基化。强酸性HBeta-M具有比H型丝光沸石纳米片（3.3×10 –2 s –1）和蒙脱石（4.0×10 –2）更高的固有活性，其初始转换频率为11×10 –2 s –1。 s –1）催化剂。实验和表征结果表明，酸性催化剂上存在两条平行的反应路线。一种途径是苯甲醇与对甲苯磺酰胺的反应（途径I）。另一途径是路线I中产生的二苯甲醚与对甲苯磺酰胺（路线II）的反应，这在本工作中发现。路线I的反应速率（13×10 –3 mol kg –1 s –1）高于路线II的反应速率（9.8×10 –3 mol kg –1 s –1））在HBeta-M上），但路线II主要以高选择性促成了目标产物的形成。因此，在这项工作中提出了一个完整的反应机理。
• 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
• Cobalt-catalyzed benzylic C–H amination via dehydrogenative-coupling reaction
  作者：Yang-Hong Ye、Ji Zhang、Gao Wang、Shan-Yong Chen、Xiao-Qi Yu

  DOI：10.1016/j.tet.2011.04.054

  日期：2011.6

  An efficient direct benzylic C-H amination via dehydrogenative-coupling by using an inexpensive catalyst/oxidant (CoBr2/(BuOOBu)-Bu-t-Bu-t) system is described. Various unmodified amides including primary or secondary sulfonamides, carboxamides, and carbamates preformed well with benzylic hydrocarbons with moderate to good yields. (C) 2011 Elsevier Ltd. All rights reserved.
• DDQ-mediated direct oxidative coupling of amides with benzylic and allylic sp3 C–H bonds under metal-free conditions
  作者：D. Ramesh、U. Ramulu、K. Mukkanti、Y. Venkateswarlu

  DOI：10.1016/j.tetlet.2012.03.137

  日期：2012.6

  A simple and efficient method for the direct oxidative coupling of amides with benzylic and allylic sp(3) C-H bonds using DDQ as an oxidant is described. A range of amides including benzamide, benzyl carbamate, and substituted sulfonamides reacted efficiently with various benzylic and allylic substrates under metal free conditions to afford amidation products in good to excellent yields. (C) 2012 Elsevier Ltd. All rights reserved.