methyl 1-acetyl-5-amino-1H-1,2,4-triazole-3-carboxylate | 117688-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 1-acetyl-5-amino-1H-1,2,4-triazole-3-carboxylate
• 英文别名: 1-Acetyl-5-amino-1,2,4-triazol-3-carbonsaeure-methylester；Methyl 1-acetyl-5-amino-1,2,4-triazole-3-carboxylate
• CAS: 117688-34-3
• 化学式: C₆H₈N₄O₃
• 分子量: 184.155
• InChiKey: ZLUARKDUOPJRAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,3-Diazido-2-cyanacrylsaeure-methylester 、 乙酰肼 以 二氯甲烷 为溶剂， 反应 16.0h， 以38%的产率得到methyl 1-acetyl-5-amino-1H-1,2,4-triazole-3-carboxylate
  参考文献：
  名称：

  Saalfrank, Rolf W.; Wirth, Uwe, Chemische Berichte, 1989, vol. 122, p. 519 - 522

  摘要：

  DOI：

文献信息

• Synthesis, Structure and Properties of N-Acetylated Derivatives of Methyl 5-Amino-1H-[1,2,4]triazole-3-carboxylate
  作者：Anetta Dżygiel、Barbara Rzeszotarska、Elżbieta Masiukiewicz、Piotr Cmoch、Bohdan Kamieński

  DOI：10.1248/cpb.52.192

  日期：——

  Methyl 5-amino-1H-[1,2,4]triazole-3-carboxylate hydrochloride (1) and free ester (2) were obtained and 2 was reacted with Ac2O to give the acetylated products 3—6. Compounds 1—6 were studied using HPLC, GC-MS, FTIR and multinuclear NMR spectroscopy, including the cross-polarisation magic angle spinning (CPMAS) technique. The results of the acetylation of 2 were compared to those of the acetylation of 5-amino-1H-[1,2,4]triazole, and for 2 a significant decrease in the susceptibility to acetylation was found. The reaction of 2 with Ac2O at 20 °C, regardless of the amount and the concentration of the latter, including neat Ac2O, proceeds fully regioselectively and leads to one product: methyl 1-acetyl-5-amino-1H-[1,2,4]triazole-3-carboxylate (3). In sharp contrast to 5-amino-1H-[1,2,4]triazole, neither an additional monoacetylated isomer, whether annular or exocyclic, nor any diacetylated derivative could be detected. The diacetylation of 2 requires the process to be carried out in neat boiling Ac2O and, as in the case of 5-amino-1H-[1,2,4]triazole, gives two diacetylated isomers. These are methyl 1-acetyl-3-(acetylamino)-1H-[1,2,4]triazole-5-carboxylate (4) and 1-acetyl-5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (5). Hypothetical pathways of their formation have been suggested. A mixture of 4 and 5 upon hydrolysis of the ring acetyl group gives the monoacetylated derivative methyl 5-(acetylamino)-1H-[1,2,4]triazole-3-carboxylate (6). The spectroscopic, structural and conformational characteristics of compounds 1—6 have been given and methods for their preparation have been provided.

  ino)-1H-[1,2,4]triazole-3-carboxylate (6)。
• SAALFRANK, ROLF W.;WIRTH, UWE, CHEM. SER., 122,(1989) N, C. 519-522
  作者：SAALFRANK, ROLF W.、WIRTH, UWE

  DOI：——

  日期：——
• MULTISUBSTITUTED AROMATIC COMPOUNDS AS INHIBITORS OF THROMBIN
  申请人：Verseon International Corporation

  公开号：EP2560966B1

  公开（公告）日：2021-01-06