3-H-1,2,3-benzoxathiazole 2,2-dioxide | 136061-92-2

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 3-H-1,2,3-benzoxathiazole 2,2-dioxide
• 英文别名: 3H-1,2,3-Benzoxathiazole, 2,2-dioxide；3H-1,2λ6,3-benzoxathiazole 2,2-dioxide
• CAS: 136061-92-2
• 化学式: C₆H₅NO₃S
• 分子量: 171.177
• InChiKey: DRLUWQXJGGKULE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-H-1,2,3-benzoxathiazole 2,2-dioxide 、 碘甲烷 在 sodium hydride 作用下， 生成 3-methyl-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
• 作为产物：
  描述：

  3-(p-tolylsulfonyl)-1,2,3-benzoxathiazole 2,2-dioxide 在 potassium fluoride 作用下， 以 水 、 乙腈 为溶剂， 以93%的产率得到3-H-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

• N-Alkoxymethylation of Secondary Amides, Sulfonamides and Phosphamides Using Dialkoxymethanes in the Presence of Lewis Acids
  作者：Witold Danikiewicz、Rafa Szmigielski

  DOI：10.1055/s-2003-37116

  日期：——

  A convenient and efficient one-pot synthesis of N-alkoxymethyl derivatives of secondary amides, sulfonamides and phosphamides in reaction with the appropriate dialkoxymethanes in the presence of a Lewis acid is described. In this method the use of toxic and carcinogenic chloromethyl alkyl ethers was eliminated.

  描述了仲酰胺、磺酰胺和磷酰胺的 N-烷氧基甲基衍生物在路易斯酸存在下与适当的二烷氧基甲烷反应的方便和有效的一锅合成。在该方法中，不再使用有毒和致癌的氯甲基烷基醚。
• Substituted and unsubstituted benzooxathiazoles and compounds derived therefrom
  申请人：——

  公开号：US20020055523A1

  公开（公告）日：2002-05-09

  The invention relates to substituted and unsubstituted 3H-benzo[1,2,3]oxathiazole 2,2-dioxides, 1,3-dihydrobenzo[1,2,5]thiadiazole 2,2-dioxides and 1,3-dihydro-benzo [c]isothiazole 2,2-dioxides, to their preparation and to their use in medicaments.

  本发明涉及取代和未取代的3H-苯并[1,2,3]噁唑-2,2-二氧化物、1,3-二氢苯并[1,2,5]噻二唑-2,2-二氧化物和1,3-二氢苯[c]异噻唑-2,2-二氧化物的制备，以及它们在药物中的应用。
• Substituted an unsubstituted benzooxathiazoles and compounds derived therefrom
  申请人：Petry Stefan

  公开号：US20050043373A1

  公开（公告）日：2005-02-24

  The invention relates to substituted and unsubstituted 3H-benzo[1,2,3]oxathiazole 2,2-dioxides, 1,3-dihydrobenzo[1,2,5]thiadiazole 2,2-dioxides and 1,3-dihydrobenzo[c]isothiazole 2,2-dioxides, to their preparation and to their use in medicaments.

  本发明涉及取代和未取代的3H-苯并[1,2,3]噁唑2,2-二氧化物、1,3-二氢苯并[1,2,5]噻二唑2,2-二氧化物和1,3-二氢苯并[c]异噻唑2,2-二氧化物，以及它们的制备和在药物中的应用。
• 1-N-phenyl-amino-1h-imidazole derivatives and pharmaceutical compositions containing them
  申请人：Lafay Jean

  公开号：US20070112009A1

  公开（公告）日：2007-05-17

  The invention relates to the compounds of formula (I): in which R 1 , R 2 , R 3 , R 4 , Q and Z are as defined in the specification. The invention also relates to the pharmaceutical compositions containing these compounds.

  本发明涉及公式（I）的化合物：其中R1，R2，R3，R4，Q和Z如规范中所定义。本发明还涉及含有这些化合物的制药组合物。
• APPARATUS AND METHOD FOR IN VIVO DELIVERY OF THERAPEUTIC AGENTS
  申请人：——

  公开号：US20010039393A1

  公开（公告）日：2001-11-08

  Electroporation electrodes are laminated to a permeable membrane to form an electrode membrane. Such an electrode membrane is useful for a continuous controlled delivery of a therapeutic agent through the skin or mucosa, when placed in direct contact with the skin or mucosa and by application of electric field pulses at specified intervals. An electrode membrane can be assembled such that it incorporates an iontophoretic electrode in the same device. This device can be jointly utilized for electroporation and iontophoretic drug delivery through the skin and mucosal membrane.

  电穿孔电极与可渗透膜层压形成电极膜。当电极膜直接与皮肤或粘膜接触，并以特定的间隔施加电场脉冲时，这种电极膜可用于通过皮肤或粘膜持续控制递送治疗剂。电极膜可以组装成在同一装置中包含离子渗透电极的形式。这种装置可共同用于通过皮肤和粘膜进行电穿孔和离子渗透给药。