5-{[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-amino}-[1,3,4]thiadiazole-2-thiol | 135983-87-8

• 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: 5-{[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-amino}-[1,3,4]thiadiazole-2-thiol
• CAS: 135983-87-8
• 化学式: C₉H₆N₄O₂S₂
• 分子量: 266.304
• InChiKey: XOWLNKXRVWRLFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.49
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.28
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5-{[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-amino}-[1,3,4]thiadiazole-2-thiol 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 7.0h， 生成 2-Ethylsulfanyl-7-(3-nitro-phenyl)-6-phenyl-6,7-dihydro-[1,3,4]thiadiazolo[3,2-a][1,3,5]triazine-5-thione
  参考文献：
  名称：

  Hetero Diels-Alder Synthesis and Fungitoxicity of New 1,3,4-Thiadiazolo[3,2-a]-s-triazine-5(H)-thiones

  摘要：

  Hetero Diels-Alder synthesis involving conjugated azomethines, 5-(arylideneamino)-2-mercapto-1,3,4-thiadiazoles IIa-c, as dienes (azadienes) and aryl isothiocyanates as dienophiles affords 2,6,7-trisubstituted 6,7-dihydro-1,3,4-thiadiazolo[3,2-a]-s-triazine-5(H)-thiones IIIa-f. The azomethines IIa-c on ethylation followed by hetero Diels-Alder reaction furnish 6,7-diaryl-2-(ethylthio)-6,7-dihydro-1,3 thiadiazolo[3,2-a]-s-triazine-5(H)-thiones IVa-f. Fungitoxicities of the compounds II-IV were evaluated in vitro aginst Aspergillus niger and Fusarium oxysporum. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.

  DOI：

  10.1021/jf00042a020
• 作为产物：
  描述：

  间硝基苯甲醛 、 2-氨基-5-巯基-1,3,4-噻二唑 以 乙醇 为溶剂， 反应 5.0h， 以78%的产率得到5-{[1-(3-Nitro-phenyl)-meth-(E)-ylidene]-amino}-[1,3,4]thiadiazole-2-thiol
  参考文献：
  名称：

  Hetero Diels-Alder Synthesis and Fungitoxicity of New 1,3,4-Thiadiazolo[3,2-a]-s-triazine-5(H)-thiones

  摘要：

  Hetero Diels-Alder synthesis involving conjugated azomethines, 5-(arylideneamino)-2-mercapto-1,3,4-thiadiazoles IIa-c, as dienes (azadienes) and aryl isothiocyanates as dienophiles affords 2,6,7-trisubstituted 6,7-dihydro-1,3,4-thiadiazolo[3,2-a]-s-triazine-5(H)-thiones IIIa-f. The azomethines IIa-c on ethylation followed by hetero Diels-Alder reaction furnish 6,7-diaryl-2-(ethylthio)-6,7-dihydro-1,3 thiadiazolo[3,2-a]-s-triazine-5(H)-thiones IVa-f. Fungitoxicities of the compounds II-IV were evaluated in vitro aginst Aspergillus niger and Fusarium oxysporum. Some of the compounds displayed activities comparable with that of the commercial fungicide Dithane M-45. Structure-activity relationships for the screened compounds are discussed.

  DOI：

  10.1021/jf00042a020