2-(5-氨基-4-氨基甲酰基-1-苯基-1H-吡唑-3-基)乙酸 | 100517-95-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-(5-氨基-4-氨基甲酰基-1-苯基-1H-吡唑-3-基)乙酸
• 英文名称: 2-(5-amino-4-carbamoyl-1-phenyl-1H-pyrazol-3-yl)acetic acid
• 英文别名: (5-amino-4-carbamoyl-1-phenyl-1H-pyrazol-3-yl)-acetic acid；(5-Amino-4-carbamoyl-1-phenyl-1H-pyrazol-3-yl)-essigsaeure；5-Amino-4-(aminocarbonyl)-1-phenyl-1H-pyrazole-3-acetic acid；2-(5-amino-4-carbamoyl-1-phenylpyrazol-3-yl)acetic acid
• CAS: 100517-95-1
• 化学式: C₁₂H₁₂N₄O₃
• 分子量: 260.252
• InChiKey: VNLLCIKBLNZQBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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-氨基-4-氨基甲酰基-1-苯基-1H-吡唑-3-基)乙酸 在 乙酸酐 作用下， 反应 3.0h， 以54%的产率得到3-amino-2-phenyl-2H-pyrazolo[4,3-c]pyridine-4,6(5H,7H)-dione
  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
• 作为产物：
  描述：

  5-氨基-4-腈基-1-苯基-3-乙腈吡唑 在 sodium hydroxide 、 水 作用下， 反应 0.83h， 以77%的产率得到2-(5-氨基-4-氨基甲酰基-1-苯基-1H-吡唑-3-基)乙酸
  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

文献信息

• The Reaction of Malononitrile with Hydrazine^1,2
  作者：Edward C. Taylor、Klaus S. Hartke

  DOI：10.1021/ja01519a044

  日期：1959.5
• Reaction of Hydrazine Hydrate and Phenylhydrazine with Malononitrile
  作者：TADASHI SATO

  DOI：10.1021/jo01089a019

  日期：1959.7
• Divergent cyclisations of 2-(5-amino-4-carbamoyl-1H-pyrazol-3-yl)acetic acids with formyl and acetyl electrophiles
  作者：Lynette A. Smyth、Thomas P. Matthews、Peter N. Horton、Michael. B. Hursthouse、Ian Collins

  DOI：10.1016/j.tet.2007.07.034

  日期：2007.9

  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.