4-tosyl-5-chloro-1,3-thiazol-2(3H)-one | 557084-20-5

• 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: 4-tosyl-5-chloro-1,3-thiazol-2(3H)-one
• 英文别名: 5-chloro-4-(4-methylphenyl)sulfonyl-3H-1,3-thiazol-2-one
• CAS: 557084-20-5
• 化学式: C₁₀H₈ClNO₃S₂
• 分子量: 289.763
• InChiKey: CULXIXMNGTVKAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  96.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tosyl-5-chloro-1,3-thiazol-2(3H)-one 在 双氧水 、 sodium methylate 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 80.0h， 生成 3-methyl-4,5-ditosyl-1,3-thiazol-2(3H)-one
  参考文献：
  名称：

  摘要：

  A series of 2-X-4-tosyl-5-chloro-1,3-thiazoles (X = OH, OAlk, SH, SAlk, NH2, NHAlk, NAlk(2), NHAr, etc.) were prepared from accessible 1-tosyl-2,2-dichloroethenyl isothiocyanate. only some of these compounds containing a moderately labile hydrogen atom peculiarly react with thiophenols in the presence of triethylamine to give 4,5-di(arylthio)-2-(hydroxy- or arylamino)-1,3-thiazoles, which are difficult to prepare by other routes. It is quite possible that, in the course of nucleophilic substitution of the chlorine atom and tosyl residue by the corresponding arylthio groups, a significant role is played by nonaromatic tautomeric forms of functionally 2-substituted 1,3-thiazoles formed by proton transfer to positions 3 and 5 of the hetero-ring.

  DOI：

  10.1023/a:1023380927159
• 作为产物：
  描述：

  5-Chloro-2-methoxy-4-(toluene-4-sulfonyl)-thiazole 在 氢溴酸 作用下， 反应 0.5h， 以90%的产率得到4-tosyl-5-chloro-1,3-thiazol-2(3H)-one
  参考文献：
  名称：

  摘要：

  Treatment of 1-tosyl-2,2-dichloroethenyl isothiocyanate with alcohols, thiols, primary and secondary amines, hydrazine and its derivatives, and phosphonium ylides results in addition of the O-, S-, N-, or C-nucleophilic center to the isothiocyanate, group, followed by cyclocondensation with elimination of hydrogen chloride and formation of the corresponding 2-functionally substituted 4-tosyl-5-chloro-1,3-thiazoles. Further transformations of these compounds were studied, and a series of previously unknown types of 3-functionally substituted 1,3-thiazole derivatives were prepared.

  DOI：

  10.1023/a:1023337112138