6-Anilino-3-methyl-4,7(2H)-indazolchinon | 145161-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-Anilino-3-methyl-4,7(2H)-indazolchinon
• 英文别名: 6-anilino-3-methyl-2H-indazole-4,7-dione
• CAS: 145161-54-2
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: XWMDPMIFTCZDLI-UHFFFAOYSA-N

物化性质

• 沸点：
  530.2±50.0 °C(Predicted)
• 密度：
  1.461±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.85
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  重氮乙烷 、 2,5-环己二烯-1,4-二酮,2-(苯基氨基)- 以 乙醚 为溶剂， 反应 0.17h， 以1.9 g的产率得到6-Anilino-3-methyl-4,7(2H)-indazolchinon
  参考文献：
  名称：

  Zur Synthese und Struktur derp-Indazolchinone und ihrer Methylierungsprodukte Untersuchungen �ber Chinone, 8. Mitt.

  摘要：

  The p-benzoquinones 5 e-j react with diazomethane (after dehydrogenation) to 6-anilino- 2e, dimethylamino- 2h, phenylthio- 2i, and methylthioindazolquinone 2 j. Methylation with dimethylsulfate of these as well as of the already known indazolquinones 6-toluidino- 2 f, 6-methylanilino- 2 g, 5-tert.butyl- 2 m, 5,6-methyl- (isomer mixture) 2 l, n, and benz-indazolquinone 2 o yield the 1- and 2-N-methyl derivatives 3 and 4. The structure of the 2-methyl derivatives is established by reaction of the corresponding benzoquinones with 3-methylsydnon in the case of 4 e, 4 g. UV/VIS-, IR- and H-1-NMR-spectroscopy (in CDCl3 and DMSO) were used for structure determination. Comparison of the UV/VIS-spectra of 2 - 4 shows that the indazolquinones are existing as 2 H-4,7-diones. For the structure elucidation of the 1- rs. 2-methylderivatives (which can be attributed to the methylation products) NMR-spectroscopy is well suited even without knowing the second isomer (solvent-effect). The course of the reaction of quinones with diazomethane and of the methylation reactions of the indazolquinones is discussed.

  DOI：

  10.1007/bf00812321