2-(4-chlorophenyl)-8a-hydroxy-7,7-dimethyl-6,8-dihydro-4aH-[1,2,4]triazolo[5,1-b][1,3]benzothiazol-5-one | 170882-51-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-chlorophenyl)-8a-hydroxy-7,7-dimethyl-6,8-dihydro-4aH-[1,2,4]triazolo[5,1-b][1,3]benzothiazol-5-one
• CAS: 170882-51-6
• 化学式: C₁₆H₁₆ClN₃O₂S
• 分子量: 349.841
• InChiKey: MZCKPWXPGMOLNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-8a-hydroxy-7,7-dimethyl-6,8-dihydro-4aH-[1,2,4]triazolo[5,1-b][1,3]benzothiazol-5-one 在 PPA 作用下， 反应 6.0h， 以78%的产率得到2-(4-Chloro-phenyl)-7,7-dimethyl-7,8-dihydro-6H-benzo[4,5]thiazolo[3,2-b][1,2,4]triazol-5-one
  参考文献：
  名称：

  Synthesis of 2-aryl-6,6-dimethyl-8-oxo-5,6,7,8-tetrahydro-1,2,4-4H-triazolo[3,2-b]benzothiazoles and their 3-aryl-[3,4-b] isomers

  摘要：

  Condensation of 3-aryl-5-thio-1,2,4-4H-trizoles (2a-i) and 2-bromodimedone (3) in THF/benzene gave 2-aryl-6,6-dimethyl-8-oxo-5a-hydroxy-5,5a,6,7,8,8a-hexahydro-1,2,4-4H-triazolo [3,2-b]benzothiazoles (5a-i). These were also obtained by a one step synthesis on heating a mixture of dimedone, NBS, and 2a-i in benzene containing a trace of benzoyl peroxide. Thermal dehydration of 5a-i in PPA/anhydrous ethanol yielded the corresponding 2-aryl-6,6-dimethyl-8-oxo-5,6,7,8-tetrahydro-1,2,4-4H-triazolo[3,2-b]benzothiazoles (6a-i). The formation of [3,4-b] fused isomers (4a-i) during the reaction of 2 with 3 was ruled out by an unambiguous synthesis of 8a-i. Antibacterial screening of selected compounds against Escherichia coli and Staphylococcus aureus was not encouraging.

  DOI：

  10.1007/bf00807167
• 作为产物：
  描述：

  2-溴-5,5-二甲基-1,3-环己二酮 、 5-(4-氯苯基)-2,4-二氢-[1,2,4]-三唑-3-硫酮 以 四氢呋喃 为溶剂， 反应 56.0h， 以54%的产率得到2-(4-chlorophenyl)-8a-hydroxy-7,7-dimethyl-6,8-dihydro-4aH-[1,2,4]triazolo[5,1-b][1,3]benzothiazol-5-one
  参考文献：
  名称：

  Synthesis of 2-aryl-6,6-dimethyl-8-oxo-5,6,7,8-tetrahydro-1,2,4-4H-triazolo[3,2-b]benzothiazoles and their 3-aryl-[3,4-b] isomers

  摘要：

  Condensation of 3-aryl-5-thio-1,2,4-4H-trizoles (2a-i) and 2-bromodimedone (3) in THF/benzene gave 2-aryl-6,6-dimethyl-8-oxo-5a-hydroxy-5,5a,6,7,8,8a-hexahydro-1,2,4-4H-triazolo [3,2-b]benzothiazoles (5a-i). These were also obtained by a one step synthesis on heating a mixture of dimedone, NBS, and 2a-i in benzene containing a trace of benzoyl peroxide. Thermal dehydration of 5a-i in PPA/anhydrous ethanol yielded the corresponding 2-aryl-6,6-dimethyl-8-oxo-5,6,7,8-tetrahydro-1,2,4-4H-triazolo[3,2-b]benzothiazoles (6a-i). The formation of [3,4-b] fused isomers (4a-i) during the reaction of 2 with 3 was ruled out by an unambiguous synthesis of 8a-i. Antibacterial screening of selected compounds against Escherichia coli and Staphylococcus aureus was not encouraging.

  DOI：

  10.1007/bf00807167