N-(p-tolylsulfonyl)-1-naphthylamine-8-sulfonic acid | 130955-98-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(p-tolylsulfonyl)-1-naphthylamine-8-sulfonic acid
• 英文别名: 8-(toluene-4-sulfonylamino)-naphthalene-1-sulfonic acid；8-(Toluol-4-sulfonylamino)-naphthalin-1-sulfonsaeure；8-p-Toluolsulfamino-naphthalin-sulfonsaeure-(1)；8-[(4-Methylphenyl)sulfonylamino]naphthalene-1-sulfonic acid
• CAS: 130955-98-5
• 化学式: C₁₇H₁₅NO₅S₂
• 分子量: 377.442
• InChiKey: WMZMQMHWTAWORD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  100.54
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-(p-tolylsulfonyl)-1-naphthylamine-8-sulfonic acid 、 氯化重氮苯 、 alkaline earth salt of/the/ methylsulfuric acid 生成 5-phenylazo-8-(toluene-4-sulfonylamino)-naphthalene-1-sulfonic acid
  参考文献：
  名称：

  Morgan; Grist, Journal of the Chemical Society, 1921, vol. 119, p. 608

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(p-tolylsulfonyl)-1,8-naphthosultam 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以8%的产率得到1,8-萘磺内酰胺
  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

• Finzi, Annali di Chimica Applicata, vol. 15, p. 53
  作者：Finzi

  DOI：——

  日期：——