2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl)acetic acid | 98335-43-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl)acetic acid
• 英文别名: (5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl)-acetic acid；(5-Amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl)-essigsaeure；5-Amino-4-(aminocarbonyl)-1-methyl-1H-pyrazole-3-acetic acid；2-(5-amino-4-carbamoyl-1-methylpyrazol-3-yl)acetic acid
• CAS: 98335-43-4
• 化学式: C₇H₁₀N₄O₃
• 分子量: 198.181
• InChiKey: RIJVUDAZNJKMEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl)acetic acid 在 盐酸 作用下， 生成 3-amino-2-methyl-2H-pyrazolo[4,3-c]pyridine-4,6(5H,7H)-dione
  参考文献：
  名称：

  The Reaction of Malononitrile with Hydrazine^1,2

  摘要：

  DOI：

  10.1021/ja01519a044
• 作为产物：
  描述：

  2-氨基-1-丙烯基-1,1,3-三甲腈 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 5.75h， 生成 2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl)acetic acid
  参考文献：
  名称：

  Divergent cyclisations of 2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl)acetic acids with formyl and acetyl electrophiles

  摘要：

  The reaction of 2-(5-amino-4-carbamoyl-1-methyl-1H-pyrazol-3-yl) acetic acid and triethylorthoformate did not give the expected dihydropyrazolo[4,3-c]pyridin-4-one product as described in literature, but formed an alternative cyclic imide product, fully characterised by NMR and X-ray crystallography. This mode of reaction was shown to be general to other 1-substituted-2-(5-amino-4-carbamoyl-1H- pyrazol-3-yl) acetic acids. The outcome of the cyclisation was highly sensitive both to the nature of the reagents used and also to the acidity of the reaction medium, such that a number of interesting bicyclic heterocycles could be produced in a controlled fashion from the single starting material. The major tautomeric forms of the bicyclic products in solution were found to vary according to their substitution pattern. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.034