3H-吡唑并[3,4-d]嘧啶,3-重氮基-4-甲基-6-苯基- | 139438-65-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 3H-吡唑并[3,4-d]嘧啶,3-重氮基-4-甲基-6-苯基-
• 英文名称: 3-diazo-4-methyl-6-phenyl-1H-pyrazolo<3,4-d>pyrimidine
• 英文别名: 3-diazo-4-methyl-6-phenylpyrazolo[3,4-d]pyrimidine
• CAS: 139438-65-6
• 化学式: C₁₂H₈N₆
• 分子量: 236.236
• InChiKey: CUPDBGQXBDNBKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  52.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3H-吡唑并[3,4-d]嘧啶,3-重氮基-4-甲基-6-苯基- 在 盐酸羟胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以56%的产率得到3-azido-4-methyl-6-phenyl-1H-pyrazolo<3,4-d>pyrimidine
  参考文献：
  名称：

  Tricyclic heteroaromatic systems containing a bridgehead nitrogen atom. Part 3. [1,2,4]Triazolo[3′,4′ : 3,2]pyrazolo[3,4-d]pyrimidines, tetrazolo[1′,5′ : 1,5]pyrazolo[3,4-d]pyrimidines and pyrimido-[5′,4′ : 4,5]pyrazolo[3,2-c][1,2,4]triazines

  摘要：

  6-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one 16 has been prepared and converted into its 3-chloro 6, 3-thioxo 17 and 3-methylthio derivatives 9. Each of these could be converted into the 3-hydrazino derivative 3, cyclisation of which with carbon disulfide or triethyl orthoformate generated the fused 1,2,4-triazoles 23 and 20, respectively. Alternatively, the hydrazino derivative 3 gave a substituted hydrazide 26 or thiosemicarbazide 25, from which the 1,2,4-triazoles 21 and 22 respectively were obtained. The equilibrium between 3-azido-6-phenyl-1H-pyrazolo[3,4-d]-pyrimidine 5 and 2-phenyl-9H-tetrazolo[1'5': 1,5]pyrazolo[3,4-d]pyrimidine 27 was studied.3-Diazo-4-methyl-6-phenyl-1H-pyrazolo[3,4-d]pyrimidine 29 was prepared by diazotisation of the corresponding amine 1 and converted into the 3-azido compound 4, which could not be cyclised to form a tetrazole. Finally, the diazo compound 29 readily formed the pyrimido[5'4':4,5]pyrazolo[3,2-c][1,2,4]triazine derivatives 32 and 33, when treated with pentane-2,4-dione and ethyl acetoacetate respectively.

  DOI：

  10.1039/p19920000239
• 作为产物：
  描述：

  3-amino-4-methyl-6-phenyl-pyrazolo[3,4-d]pyrimidine 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 0.5h， 以83%的产率得到3H-吡唑并[3,4-d]嘧啶,3-重氮基-4-甲基-6-苯基-
  参考文献：
  名称：

  Tricyclic heteroaromatic systems containing a bridgehead nitrogen atom. Part 3. [1,2,4]Triazolo[3′,4′ : 3,2]pyrazolo[3,4-d]pyrimidines, tetrazolo[1′,5′ : 1,5]pyrazolo[3,4-d]pyrimidines and pyrimido-[5′,4′ : 4,5]pyrazolo[3,2-c][1,2,4]triazines

  摘要：

  6-Phenyl-1H-pyrazolo[3,4-d]pyrimidin-3(2H)-one 16 has been prepared and converted into its 3-chloro 6, 3-thioxo 17 and 3-methylthio derivatives 9. Each of these could be converted into the 3-hydrazino derivative 3, cyclisation of which with carbon disulfide or triethyl orthoformate generated the fused 1,2,4-triazoles 23 and 20, respectively. Alternatively, the hydrazino derivative 3 gave a substituted hydrazide 26 or thiosemicarbazide 25, from which the 1,2,4-triazoles 21 and 22 respectively were obtained. The equilibrium between 3-azido-6-phenyl-1H-pyrazolo[3,4-d]-pyrimidine 5 and 2-phenyl-9H-tetrazolo[1'5': 1,5]pyrazolo[3,4-d]pyrimidine 27 was studied.3-Diazo-4-methyl-6-phenyl-1H-pyrazolo[3,4-d]pyrimidine 29 was prepared by diazotisation of the corresponding amine 1 and converted into the 3-azido compound 4, which could not be cyclised to form a tetrazole. Finally, the diazo compound 29 readily formed the pyrimido[5'4':4,5]pyrazolo[3,2-c][1,2,4]triazine derivatives 32 and 33, when treated with pentane-2,4-dione and ethyl acetoacetate respectively.

  DOI：

  10.1039/p19920000239