methyl 2-[((3-cyano-6-nitro-1-phenyl)-1H-indazol-4-yl)sulfonyl]acetate | 663622-99-9

• 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 2-[((3-cyano-6-nitro-1-phenyl)-1H-indazol-4-yl)sulfonyl]acetate
• 英文别名: methyl 2-(3-cyano-6-nitro-1-phenylindazol-4-yl)sulfonylacetate
• CAS: 663622-99-9
• 化学式: C₁₇H₁₂N₄O₆S
• 分子量: 400.371
• InChiKey: RAPLAIOKIONJQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 2-[((3-cyano-6-nitro-1-phenyl)-1H-indazol-4-yl)sulfonyl]acetate 在 potassium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 8.0h， 以55%的产率得到methyl 3-amino-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：

  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
• 作为产物：
  描述：

  methyl 2-[(3-cyano-6-nitro-1-phenyl-1H-indazol-4-yl)thio]acetic acid 在 双氧水 、 三氟乙酸 作用下， 反应 1.0h， 以92%的产率得到methyl 2-[((3-cyano-6-nitro-1-phenyl)-1H-indazol-4-yl)sulfonyl]acetate
  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

文献信息

• ——
  作者：A. M. Starosotnikov、S. A. Shevelev

  DOI：10.1023/a:1026012922607

  日期：——

  Oxidation of 3-substituted 4-R-6-nitro-1-phenyl-1H-indazoles and benzo[d]isoxazoles (R = Ph, CH2CO2Me) gave the corresponding sulfones treatment of which with PhSH-K2CO3 in N-methylpyrrolidone results in replacement of only the RSO2 group in position 4 with the 6-NO2 group remaining intact, contrary to the known sequence of nucleophilic substitution for meta-arranged nucleofuges.