4-甲基-1,3,5-噻嗪并[1,2-a]苯并咪唑-2-胺 | 78650-16-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: 4-甲基-1,3,5-噻嗪并[1,2-a]苯并咪唑-2-胺
• 中文别名: 4-甲基-1,3,5-三嗪并[1,2-a]苯并咪唑-2-胺
• 英文名称: 2-amino-4-methyl-s-triazino[1,2-a]benzimidazole
• 英文别名: 4-methyl[1,3,5]triazino[1,2-a]benzimidazol-2-amine；4-methyl-[1,3,5]triazino[1,2-a]benzimidazol-2-amine
• CAS: 78650-16-5
• 化学式: C₁₀H₉N₅
• mdl: MFCD04155098
• 分子量: 199.215
• InChiKey: JYUMVHXSEQXABG-UHFFFAOYSA-N

物化性质

• 熔点：
  324-325 °C
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为产物：
  描述：

  2-胍基苯并咪唑 、 2-甲基-1,3-苯并恶嗪-4-酮,高氯酸 在 sodium 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以30%的产率得到4-甲基-1,3,5-噻嗪并[1,2-a]苯并咪唑-2-胺
  参考文献：
  名称：

  Reactions of 4-oxo-1,3-benzoxazinium perchlorates with guanidines

  摘要：

  Condensation of 2-methyl-4-oxo-1,3-benzoxazinium perchlorate with various aromatic and heterocyclic aldehydes provided previously unknown arylvinyl- and hetarylvinyl-substituted salts whose recyclization under treatment with guanidine resulted in formerly undescribed 1,3,5-triazines. The reaction of perchlorates obtained with guanidinebenzoxazole led to the formation of bishetarylamines, with guanidinebenzimidazole formed triazinebenzimidazoles, the cyanoguanidine reacted with 4-oxo-1,3-benzoxazinium perchlorates to give cyanamides.

  DOI：

  10.1134/s1070428007100259

文献信息

• Synthesis of 2-amino-<i>s</i>-triazino[1,2-<i>a</i>]benzimidazoles as potential antifolates from 2-guanidino- and 2-guanidino-5-methylbenzimidazoles
  作者：Anton V. Dolzhenko、Wai-Keung Chui

  DOI：10.1002/jhet.5570430115

  日期：2006.1

  regioselectivity was not observed in any of these reactions. However, the synthesis of s-triazino[1,2-a]benzimidazole system was found to be more regioselective than its 3,4-dihydro analogue. NOESY experiment indicated that the compound, 2-amino-4,4-dimethyl-3,4-dihydro-s-triazino[1,2-a]benzimidazole existed predominantly as the 3,4-dihydro tautomer in dimethyl sulfoxide. It was found to inhibit bovine dihydrofolate

  2-氨基的合成小号-triazino [1,2一]苯并咪唑由2- guanidinobenzimidazoles通过一个环成环反应顺利进行。研究了5-甲基-2-胍基苯并咪唑与偶氮二羧酸二乙酯，醛，丙酮，乙氧基亚甲基丙二酸二乙酯和原酸酯的闭环区域化学，导致形成s-三嗪环。在任何这些反应中均未观察到高区域选择性。然而，发现s-三嗪并[1,2- a ]苯并咪唑系统的合成比其3,4-二氢类似物具有更高的区域选择性。NOESY实验表明，化合物，2-氨基-4,4-二甲基-3,4-二氢小号-triazino [1,2一]苯并咪唑主要以3,4-二氢互变异构体的形式存在于二甲基亚砜中。发现抑制IC 50 10.9μM的牛二氢叶酸还原酶。
• Martin, Dieter; Graubaum, Heinz; Kempter, Gerhard, Journal fur praktische Chemie (Leipzig 1954), 1981, vol. 323, # 2, p. 303 - 310
  作者：Martin, Dieter、Graubaum, Heinz、Kempter, Gerhard、Ehrlichmann, Werner

  DOI：——

  日期：——
• MARTIN D.; GRAUBAUM H.; KEMPTER G.; EHRLICHMANN W., J. PRAKT. CHEM., 1981, 323, NO 2, 303-310
  作者：MARTIN D.、 GRAUBAUM H.、 KEMPTER G.、 EHRLICHMANN W.

  DOI：——

  日期：——
• Reactions of 4-oxo-1,3-benzoxazinium perchlorates with guanidines
  作者：E. Yu. Suvorova、N. I. Vikrishchuk、L. D. Popov、Z. A. Starikova、A. D. Vikrishchuk、Yu. A. Zhdanov

  DOI：10.1134/s1070428007100259

  日期：2007.10

  Condensation of 2-methyl-4-oxo-1,3-benzoxazinium perchlorate with various aromatic and heterocyclic aldehydes provided previously unknown arylvinyl- and hetarylvinyl-substituted salts whose recyclization under treatment with guanidine resulted in formerly undescribed 1,3,5-triazines. The reaction of perchlorates obtained with guanidinebenzoxazole led to the formation of bishetarylamines, with guanidinebenzimidazole formed triazinebenzimidazoles, the cyanoguanidine reacted with 4-oxo-1,3-benzoxazinium perchlorates to give cyanamides.