6-p-Toluidino-4,7(2H)-indazolchinon | 145161-72-4

• 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: 6-p-Toluidino-4,7(2H)-indazolchinon
• 英文别名: 6-(4-methylanilino)-1H-indazole-4,7-dione
• CAS: 145161-72-4
• 化学式: C₁₄H₁₁N₃O₂
• 分子量: 253.26
• InChiKey: UOTANJOUXULPIM-UHFFFAOYSA-N

物化性质

• 沸点：
  504.1±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)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-p-Toluidino-4,7(2H)-indazolchinon 、 乙酸酐 反应 0.5h， 以93%的产率得到2-Acetyl-6-p-toluidino-4,7(2H)-indazolchinon
  参考文献：
  名称：

  Untersuchungen �ber Chinone, 9. Mitt. �ber Acetylderivate vonp-Indazolchinonen

  摘要：

  Acetylation of the indazolquinones 1a (6-anilino-), b (6-p-toluidino-), c (6-N-methylanilino-), g (6- or 5-methylthio-), and k (benz[f]-) by heating with acetic anhydride yields the 2-acetylindazolquinones 4a, b, c, g, and k. Reductive acetylation of the quinones 1c, g, h/h(1) (6/5-methyl), k and - for structure elucidation - their 1-N- (2c) and 2-N- (3c, 3e)-methyl derivatives with acetic anhydride, zink powder, and sodium acetate gives the 1-acetyl- (7c, g, h/h(1), k), resp. 1-methyl- (8c), and 2-methyl- (9c, e) diacetoxyindazoles. In case of 1k, two diacetyl derivatives were isolated in addition to the already known triacetyl derivative 7k, regardless of the conditions chosen. Acetylation of the intermediate product of the reaction from phenylthio-benzoquinone with diazomethane also yields a triacetylhydroquinone (7f). UV/Vis, IR, and (1)HNMR spectroscopy were used for structure determination. Comparison of the UV/Vis spectra of the acetyl derivatives 4 with those of 1, 2, 3, and of compounds 7 with those of analog substituted indazols shows that the acetyl group is located in position 2 with compounds 4 and in position 1 with compounds 7. By means of (1)HNMR spectra the position of the acetyl group can be determined by the effect of the carbonyl group on the proton in position 3.

  DOI：

  10.1007/bf00812709

文献信息

• Zur Synthese und Struktur derp-Indazolchinone und ihrer Methylierungsprodukte Untersuchungen �ber Chinone, 8. Mitt.
  作者：Robert Ott、Erfried Pinter

  DOI：10.1007/bf00812321

  日期：——

  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.
• Ott R., Pinter E., Monatsh. Chem, 125 (1994) N 8-9, S 945-954
  作者：Ott R., Pinter E.

  DOI：——

  日期：——