N-(5-acetyl-2-hydroxyphenyl)-4-toluenesulfonamide | 136061-91-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(5-acetyl-2-hydroxyphenyl)-4-toluenesulfonamide
• 英文别名: N-(5-Acetyl-2-hydroxyphenyl)-4-methylbenzenesulfonamide
• CAS: 136061-91-1
• 化学式: C₁₅H₁₅NO₄S
• 分子量: 305.354
• InChiKey: LVZWOEVOPMZQCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  91.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(5-acetyl-2-hydroxyphenyl)-4-toluenesulfonamide 在 磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 3-(p-tolylsulfonyl)-5-acetyl-1,2,3-benzoxathiazole 2,2-dioxide
  参考文献：
  名称：

  1,2,3-Benzoxathiazole 2,2-dioxides: synthesis, mechanism of hydrolysis, and reactions with nucleophiles

  摘要：

  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.

  DOI：

  10.1021/jo00023a012

文献信息

• Palladium-catalyzed oxamidation of alkenes: A new approach to benzoxazolidines
  作者：Niranjan Panda、Sushree Arpitabala Yadav

  DOI：10.1016/j.tet.2018.02.012

  日期：2018.3

  A novel palladium catalyzed protocol for the synthesis of benzoxazolidine by the reaction sulfamidophenol and terminal alkene was developed. This oxamidation process is simple and does not require any ligand, base or inert atmosphere for the overall transformation. From control experiments, it is apparent that the cross-coupling reaction proceeds with initial formation of enesulfonamide which undergoes

  提出了一种新的钯催化方案，其通过磺酰胺基苯酚和末端烯烃的反应合成苯并恶唑烷。该乙酰胺化过程很简单，不需要任何配体，碱或惰性气氛即可进行整体转化。从对照实验中可以明显看出，交叉偶联反应是随着烯磺酰胺的初步形成而进行的，该烯磺酰胺通过分子内的环化反应而被核仁酸化，随后被TsOH进行原去palpalpalpal化，从而得到苯并恶唑烷。