1,3,8-trimethyl-8-azaxanthine | 1632-30-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 1,3,8-trimethyl-8-azaxanthine
• 英文别名: 2,4,6-trimethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione；2,4,6-trimethyltriazolo[4,5-d]pyrimidine-5,7-dione
• CAS: 1632-30-0
• 化学式: C₇H₉N₅O₂
• 分子量: 195.181
• InChiKey: QENRIORRNMNJEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  71.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3,7,9-tetramethyl-8-azaxanthinium benzenesulfonate 以77%的产率得到
  参考文献：
  名称：

  KOLESOVA M. B.; MURAVICH-ALEKSANDR X. L.; SMIRNOVA N. V.; GIRSHOVICH M. Z+, ZH. ORGAN. XIMII, 1981, 17, HO 5, 1080-1087

  摘要：

  DOI：

文献信息

• Synthesis and Regioselective N- and O-Alkylation of 1<i>H</i>- or 3<i>H</i>-[1,2,3]Triazolo[4,5-<i>d</i>]pyrimidine-5,7(4<i>H</i>,6<i>H</i>)-diones (8-Azaxanthines) and Transformation of Their 3-Alkyl Derivatives into 1-Alkyl Isomers
  作者：Tomohisa Nagamatsu、Rafiqul Islam

  DOI：10.1055/s-2006-950337

  日期：——

  alkylating agents, for example alkyl halides and dimethyl sulfate, were employed in aprotic Solvents Under a variety of conditions for the alkylation of mono- and disubstituted 1H- or 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones, which were prepared by cyclization of the appropriate 5,6-diaminouracils with nitrous acid. The alkylation on the triazole ring in the presence of anhydrous potassium carbonate

  在非质子溶剂中使用了几种烷基化剂，例如卤代烷和硫酸二甲酯 在各种条件下用于单取代和双取代的 1H-或 3H-[1,2,3]三唑并[4,5-d]的烷基化嘧啶-5,7(4H,6H)-二酮，通过适当的 5,6-二氨基尿嘧啶与亚硝酸的环化制备。在无水碳酸钾存在下，三唑环上的烷基化同时在 1 位和 2 位发生，优先在 2 位烷基化。用等价的烷基化试剂在嘧啶环上进行类似的烷基化仅在 4 位发生。3,6-二取代衍生物在室温下烷基化导致5-O-烷基化伴随4-N-烷基化，但在高温下仅发生4-N-烷基化。3,4的反应，
• Study of the prototropic tautomerism of 8-azatheophylline by13C and15N NMR spectroscopy
  作者：Gerrit L'abbé、Marie-Anne Persoons、Suzanne Toppet

  DOI：10.1002/mrc.1260250418

  日期：1987.4

  Comparison of the 13C and 15N NMR spectra of 8‐azatheophylline with those of its three methylated derivatives and other model compounds from the literature showed that 8‐azatheophylline exists to the extent of 80% in the N‐2 tautomeric form in DMSO solution.

  8-氮杂茶碱的 13C 和 15N NMR 光谱与其三种甲基化衍生物和文献中其他模型化合物的比较表明，8-氮杂茶碱在 DMSO 溶液中以 N-2 互变异构形式存在的程度高达 80%。
• Kolesova, M. B.; Muravich-Aleksandr, Kh. L.; Smirnova, N. V., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, p. 954 - 960
  作者：Kolesova, M. B.、Muravich-Aleksandr, Kh. L.、Smirnova, N. V.、Girshovich, M. Z.

  DOI：——

  日期：——
• Muravich-Aleksandr, Kh. L.; Kolesova, M. B.; Pernikova, V. G., Journal of Organic Chemistry USSR (English Translation), 1983, vol. 19, # 3, p. 562 - 567
  作者：Muravich-Aleksandr, Kh. L.、Kolesova, M. B.、Pernikova, V. G.、Smirnova, N. V.

  DOI：——

  日期：——
• Regioselective N- and O-Alkylation of 3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (8-Azaxanthines) and Transformation of 3-Alkyl Derivatives into 1-Alkyl Isomers
  作者：Tomohisa Nagamatsu、Rafiqul Islam

  DOI：10.3987/com-06-10807

  日期：——

  The alkylation on the pyrimidine ring of 3-methyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-diones (1) with an equimolecular amount of alkylating agent in the presence of anhydrous potassium carbonate in aprotic solvents under heating took place only at the 4-position. The similar alkylation on the triazole ring of 6-methyl-1H-[1,2,3]triazolo[4,5-d]-pyrimidine5,7(4H,6H)-diones (4) with an equivalent alkylating reagent happened simultaneously at the 1- and 2-positions with the priority at the 2-position. On the other hand, the alkylation of 3,6-disubstituted derivatives (12a-d) at room temperature led to the 5-O-alkylation (14a-e) accompanied with the 4-N-alkylation (3a, 13a-d), but at high temperature only the 4-N-alkylation occurred. The 3,4,6-tri-substituted derivatives (3a, 13d) underwent transformation with excess alkylating agents at high temperature leading to the formation of 1,4,6-tri-substituted derivatives (7, 15) with elimination of the 3-substituent in the same manner as xanthine.