methyl 7-nitro-1-phenyl-1H-thiopyrano[4,3,2-cd]indazole-4-carboxylate | 545357-63-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 7-nitro-1-phenyl-1H-thiopyrano[4,3,2-cd]indazole-4-carboxylate
• 英文别名: Methyl 10-nitro-2-phenyl-7-thia-2,3-diazatricyclo[6.3.1.04,12]dodeca-1(12),3,5,8,10-pentaene-6-carboxylate
• CAS: 545357-63-9
• 化学式: C₁₇H₁₁N₃O₄S
• 分子量: 353.358
• InChiKey: CHYMVLGUUVFNDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7-nitro-1-phenyl-1H-thiopyrano[4,3,2-cd]indazole-4-carboxylate 在 双氧水 、 三氟乙酸 作用下， 反应 0.5h， 以81%的产率得到methyl 7-nitro-5,5-dioxo-1-phenyl-1,5-dihydro-5λ⁶-thiopyrano[4,3,2-cd]indazole-4-carboxylate
  参考文献：
  名称：

  Synthesis of 14π-electron peri-annelated tricyclic heteroaromatic systems based on 2,4,6-trinitrotoluene

  摘要：

  Methyl 1-aryl-7-nitro-1H-thiopyrano[4,3,2-cd]indazol-4-carboxylates 2 and 1,5-diaryl-7-nitro-1,5-dihydropyrazolo[3,4,5-de]-cinnolines 4 were prepared based on 1-aryl-3-formyl-4,6-dinitro-1H-indazoles 1, which were synthesised previously starting from 2,4,6-trinitrotoluene.

  DOI：

  10.1070/mc2002v012n05abeh001642
• 作为产物：
  描述：

  巯基乙酸甲酯 、 3-formyl-4,6-dinitro-1-phenyl-1H-indazole 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 8.0h， 以60%的产率得到methyl 7-nitro-1-phenyl-1H-thiopyrano[4,3,2-cd]indazole-4-carboxylate
  参考文献：
  名称：

  摘要：

  A method for the synthesis of peri-annelated trinuclear heterocycles, including 14pi-electron heteroaromatic systems, namely, 1H-thiopyrano[4,3,2-cd]indazoles and 1,5-dihydropyrazolo[3,4,5-de]cinnolines, from 3-R-1-aryl-4,6-dinitro-1H-indazoles was developed. The method is based on the high mobility of the NO2 group in position 4 and consists of either selective nucleophilic substitution of the 4-NO2 group on treatment with the HSCH2CO2Me-K2CO3 system followed by intramolecular cyclization of the resulting sulfide (R = CHO) or the corresponding sulfone (R = CN) formed upon its oxidation or direct intramolecular substitution of the 4-NO2 group (R = CH=NNH Ph).

  DOI：

  10.1023/a:1026056704860