4'-(二甲基氨基)-p-甲苯磺酰苯胺 | 19766-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4'-(二甲基氨基)-p-甲苯磺酰苯胺
• 中文别名: 4'-（二甲氨基）-对甲苯磺酰苯胺
• 英文名称: N-(4-(dimethylamino)phenyl)-4-methylbenzenesulfonamide
• 英文别名: 4-dimethylamino-N-p-tosylanilide；toluene-4-sulfonic acid-(4-dimethylamino-anilide)；N'-(Toluol-sulfonyl-(4))-N.N-dimethyl-p-phenylendiamin；Toluol-4-sulfonsaeure-(4-dimethylamino-anilid)；N-[4-(dimethylamino)phenyl]-4-methylbenzenesulfonamide
• CAS: 19766-55-3
• 化学式: C₁₅H₁₈N₂O₂S
• 分子量: 290.386
• InChiKey: ZBAWXYZNUKKOKU-UHFFFAOYSA-N

物化性质

• 熔点：
  147-149 °C (decomp)
• 沸点：
  447.6±55.0 °C(Predicted)
• 密度：
  1.247±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4'-(二甲基氨基)-p-甲苯磺酰苯胺 在 硫酸 、 sodium ethanolate 、 溶剂黄146 作用下， 生成 N,N,N'-三甲基苯-1,4-二胺
  参考文献：
  名称：

  Oxidation Processes. XXI.¹ The Autoxidation of the p-Phenylenediamines

  摘要：

  DOI：

  10.1021/ja01186a070
• 作为产物：
  描述：

  对甲苯亚磺酸 、 N,N-二甲基-4-亚硝基苯胺 以 aq. phosphate buffer 为溶剂， 以77%的产率得到4'-(二甲基氨基)-p-甲苯磺酰苯胺
  参考文献：
  名称：

  Electroreductive nucleophile acceptor generation. Electrochemical synthesis of N-(4-(dimethylamino)phenyl)benzenesulfonamide

  摘要：

  To the best of our knowledge, this is first report describing generation of Michael acceptor via electrochemical reduction. In this work, electrochemical reduction of 4-nitroso-N,N-dimethylaniline has been studied in the presence of arylsulfinic acids in aqueous solutions. The cathodically generated p-quinonediimine participates in Michael type addition reaction with arylsulfinic acids and converts to the corresponding sulfonamide derivatives. This work has led to the development of a facile and environmentally friendly reagent-less electrochemical method for the synthesis of some sulfonamide derivatives with safe waste under green conditions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.electacta.2015.09.031

文献信息

• A Catalytic Construction of Indoles via Formation of Ruthenium Vinylidene Species from <i>N</i> ‐Arylynamides
  作者：Masanori Tayu、Ryuta Watanabe、Satoshi Isogi、Nozomi Saito

  DOI：10.1002/adsc.202001342

  日期：2021.2.16

  with a catalytic amount of TpRuCl(PPh3)2 resulted in the construction of indole scaffolds known as privileged structure motifs. This reaction involved a cascade of 1,2‐rearrangement and cyclization carrying out C−C bond formation via a ruthenium vinylidene intermediate, as revealed by a deuterium‐labeling experiments. Furthermore, the transformation of multi‐functionalized ynamide, derived from a practical

  用催化量的TpRuCl（PPh 3）2处理酰胺，导致吲哚支架的构建被称为特权结构基序。如氘标记实验所示，该反应涉及1,2-重排和环化的级联，通过钌-亚乙烯基中间体进行CC键形成。此外，源自实用药物分子的多官能化乙酰胺的转化显示出该反应对官能团的高度耐受性。
• A simple and efficient method for sulfonylation of amines, alcohols and phenols with cupric oxide under mild conditions
  作者：G.A. Meshram、Vishvanath D. Patil

  DOI：10.1016/j.tetlet.2008.12.085

  日期：2009.3

  Cupric Oxide efficiently catalyzed the synthesis of sulfonamides and sulfonic esters. This method has been applied to a variety of substrates including nucleophilic and sterically-hindered amines, alcohols and phenols with excellent yields of sulfonamides and sulfonic esters. The remarkable selectivity under mild and neutral conditions of this commercially available inexpensive catalyst is an attractive

  氧化铜有效地催化了磺酰胺和磺酸酯的合成。该方法已应用于多种底物，包括亲核和空间受阻的胺，醇和酚，磺酰胺和磺酸酯的收率极高。这种市售廉价催化剂在温和和中性条件下的显着选择性是该方法的吸引人的特征。
• Mild and Efficient Indium Metal Catalyzed Synthesis of Sulfonamides and Sulfonic Esters
  作者：Doo Jang、Joong-Gon Kim

  DOI：10.1055/s-2007-986632

  日期：2007.10

  A facile and efficient method for synthesizing sulfon­amides was developed using a catalytic amount of indium metal. A wide range of sulfonamides were synthesized in excellent yields using the new process. The method showed a generality for substrates including less nucleophilic and sterically hindered anilines, and it is also applicable for preparing sulfonic esters from sulfonyl chlorides and alcohols.

  开发了一种简单高效的合成磺酰胺的方法，使用了催化量的铟金属。通过这一新工艺，合成了多种磺酰胺，产率优良。该方法对底物表现出广泛适应性，包括较少亲核和空间位阻的胺类，并且也适用于从磺酰氯和醇制备磺酸酯。
• Copper-catalyzed direct N-arylation of N-arylsulfonamides using diaryliodonium salts in water
  作者：Xu Geng、Song Mao、Liangshun Chen、Jianjun Yu、Jianwei Han、Jianli Hua、Limin Wang

  DOI：10.1016/j.tetlet.2014.05.082

  日期：2014.7

  An efficient copper-catalyzed N-arylation of N-arylsulfonamides with diaryliodonium salts is reported. The reaction employs diaryliodonium salts and N-arylsulfonamides in water at room temperature, giving the products in moderate to excellent yields.

  报道了一种有效的铜催化的N-芳基磺酰胺与二芳基碘鎓盐的N-芳基化反应。该反应在室温下在水中使用二芳基碘鎓盐和N-芳基磺酰胺，使产物的产率中等至优异。
• The key intermediates that interact with the fluorophores in the peroxyoxalate chemiluminescence reaction of 2,4,6-trichlorophenyl N-aryl-N-tosyloxamates
  作者：Ryu Koike、Jiro Motoyoshiya、Yutaka Takaguchi、Hiromu Aoyama

  DOI：10.1039/b300079f

  日期：2003.3.6

  A kinetic study of peroxyoxalate chemiluminescence reactions employing 2,4,6-trichlorophenyl N-aryl-N-tosyloxamates supports the 1,2-dioxetanones still bearing the eliminating group as the key intermediates that interact with the fluorophores rather than 1,2-dioxetanedione.

  使用2,4,6-三氯苯基N-芳基-N-甲苯磺酰草酸酯的过氧草酸酯化学发光反应的动力学研究支持仍带有消除基团的1,2-二氧杂环丁烷作为与荧光团而不是1,2-二氧杂环丁酮相互作用的关键中间体。

表征谱图