N-methyl-N-(2'-hydroxyphenyl)-4-toluenesulfonamide | 81256-17-9

• 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-methyl-N-(2'-hydroxyphenyl)-4-toluenesulfonamide
• 英文别名: N-methyl-N-(2-hydroxyphenyl)-4-toluenesulfonamide；toluene-4-sulfonic acid-(2-hydroxy-N-methyl-anilide)；Toluol-4-sulfonsaeure-(2-hydroxy-N-methyl-anilid)；2-p-Toluolsulfonylmethylamino-phenol；N-(2-hydroxyphenyl)-N,4-dimethylbenzenesulfonamide
• CAS: 81256-17-9
• 化学式: C₁₄H₁₅NO₃S
• 分子量: 277.344
• InChiKey: LEDGRNGTNZYMCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-甲氨基苯酚 在 正丁基锂 、 三乙胺 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-methyl-N-(2'-hydroxyphenyl)-4-toluenesulfonamide
  参考文献：
  名称：

  Substitution at tetracoordinate sulfur(VI). Rearrangement of 2-aminoaryl arenesulfonates to N-(2-hydroxyaryl)arenesulfonamides

  摘要：

  DOI：

  10.1021/jo00349a013

文献信息

• Hexafluoroisopropanol (HFIP)-prompted rearrangement of N-phenoxysulfonamides for the direct assembly of ortho-sulfonamide phenols: A combined experimental and computational study
  作者：Yi Wang、Xiaoli Chen、Shuang Lin、Hui Gao、Fu-Xiaomin Liu、Zhi Zhou、Wei Yi

  DOI：10.1016/j.tetlet.2021.153601

  日期：2022.1

  chemistry. Herein an efficient metal-free rearrangement reaction has been developed for the construction of ortho-sulfonamide phenols via HFIP-prompted intramolecular sulfonamide group 1,3-migration. This protocol features mild reaction conditions, broad functional group compatibility and good regioselectivity. Combined experimental mechanistic study and detailed DFT calculations clarified the crucial

  邻磺酰胺酚代表了药物和合成化学中一类有吸引力的结构基序。本文开发了一种有效的无金属重排反应，用于通过 HFIP 促进的分子内磺酰胺基团 1,3-迁移构建邻磺酰胺酚。该方案具有反应条件温和、官能团兼容性广、区域选择性好等特点。结合实验机理研究和详细的 DFT 计算，阐明了 HFIP 分子在促进该反应中的关键作用，并且推导出了独特的氢键网络来解释观察到的反应性。
• INK FOR SCRATCH COLORING AND SHEET WITH INVISIBLE INFORMATION PRINTED
  申请人：Mitsubishi Paper Mills Limited

  公开号：EP2096149A1

  公开（公告）日：2009-09-02

  Disclosed are a scratch color-developable ink comprising an electron-donating colorless or light-color dye precursor, an electron-accepting color developer and a varnish, wherein a solid particle component contained therein has an average particle diameter of 0.3 to 25 µm, a scratch color-developable ink comprising an electron-donating colorless or light-color dye precursor, an electron-accepting color developer and a varnish, wherein an azaphthalide compound is contained as the electron-donating colorless or light-color dye precursor, and an invisible information printed sheet obtained by printing invisible information on a support with the above scratch color-developable ink. The above scratch color-developable ink makes invisible information visible easily by scratching with a finger nail although the color of an invisible information printed portion is hard to develop by frictional contact during usual handling, gives a high developed color intensity and is free from the occurrence of dust during the visualization of invisible information.

  公开了一种由电子捐献型无色或浅色染料前体、电子接受型显色剂和光油组成的划痕显色墨水，其中包含的固体颗粒成分的平均颗粒直径为 0.3至25微米；一种可刮擦显色油墨，由电子捐赠的无色或浅色染料前体、电子接受的显色剂和光油组成，其中含有作为电子捐赠的无色或浅色染料前体的萘化合物；以及一种通过在支撑物上用上述可刮擦显色油墨印刷隐形信息而获得的隐形信息印刷品。 上述划痕显色油墨虽然在通常的操作过程中通过摩擦接触很难使隐形信息印刷部分显色，但用指甲划痕即可轻松显现隐形信息，显色强度高，而且在显现隐形信息时不会产生灰尘。
• Endocyclic nucleophilic substitution at tetracoordinate sulfur(VI)
  作者：Kenneth K. Andersen、Sumalee Chumpradit、Debra J. McIntyre

  DOI：10.1021/jo00255a005

  日期：1988.9
• Hewitt; King; Murch, Journal of the Chemical Society, 1926, p. 1358,1369
  作者：Hewitt、King、Murch

  DOI：——

  日期：——
• 1,2,3-Benzoxathiazole 2,2-dioxides: synthesis, mechanism of hydrolysis, and reactions with nucleophiles
  作者：Kenneth K. Andersen、Diana D. Bray、Sumalee Chumpradit、Michael E. Clark、Gregory J. Habgood、Colin D. Hubbard、Kathleen M. Young

  DOI：10.1021/jo00023a012

  日期：1991.11

  The rates of base-induced hydrolysis of some five-membered cyclic sulfamates, X-3-(p-tolylsulfonyl)-1,2,3-benzoxathiazole 2,2-dioxides (1a, X = H; 1b, X = 5-Me; 1c, X = 5-t-Bu; 1d, X = 5-Br; 1e, X = 5-Cl; 1f, X = 5-Ac; 1g, X = 5-NO2; 8a, X = 6-NO2) were measured in aqueous acetonitrile. The hydrolyses occurred with cleavage of the endocyclic N-SO2 bond. A Hammett plot using sigma-m values for 1a-g and sigma-p for 8a had rho = +2.20. Activation enthalpies and entropies were measured for 1a and for 3-methyl-1,2,3-benzoxathiazole 2,2-dioxide (10). Volumes of activation were determined for 1g and for 8a. The mechanistic profile for hydrolysis resembled that for the saponification of the analogous sultones and cyclic sulfates. These first examples of 1,2,3-benzoxathiazole 2,2-dioxides (1a-g, 8a) were prepared by treating N-(2-hydroxyphenyl)-p-toluenesulfonamides with sulfuryl chloride and triethylamine or by oxidizing the monoxide precursors using m-chloroperbenzoic acid. Treatment of 1a with potassium fluoride gave 1,2,3-benzoxathiazole 2,2-dioxide (9), which was methylated to give 10. Sulfamate 1a was treated with various nucleophilic reagents: phenyllithium, methyllithium, potassium fluoride, methylamine, tert-butylamine, and sodium methoxide. The first three attacked the tosyl sulfur atom and cleaved the exocyclic N-SO2 bond. The amines attacked the endocyclic sulfonyl sulfur atom and cleaved the endocyclic N-SO2 bond. Sodium methoxide attacked both sulfonyl groups.