3-(4-hydroxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophene-2-carboxylic acid | 171628-02-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(4-hydroxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophene-2-carboxylic acid
• 英文别名: O-Desmethyl thifensulfuron acid (IN-JZ789)；3-[(2-methyl-6-oxo-1H-1,3,5-triazin-4-yl)carbamoylsulfamoyl]thiophene-2-carboxylic acid
• CAS: 171628-02-7
• 化学式: C₁₀H₉N₅O₆S₂
• 分子量: 359.343
• InChiKey: UMLCJPSDEOEISZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  203
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophene-2-carboxylic acid 在 pH 4 buffer 、 水 作用下， 生成 3-(氨基磺酰基)噻吩-2-羧酸
  参考文献：
  名称：

  Hydrolysis Kinetics of Thifensulfuron Methyl in Aqueous Buffer Solutions

  摘要：

  The hydrolysis of thifensulfuron methyl and thifensulfuron were investigated in buffered aqueous solutions with pH values of 4, 5, 9, and 10. Hydrolysis of thifensulfuron methyl was pH dependent and relatively fast both in acidic and alkaline buffer solutions. In the case of thifensulfuron, hydrolysis rates were of the same order of magnitude as thifensulfuron methyl at acidic pH, but very low at alkaline pH. In acidic solutions, cleavage of the sulfonylurea bridge and O-demethylation of the methoxy group of the triazine ring occurred concurrently The resulting intermediates gave two parallel reactions: cleavage of the sulfonylurea bridge and opening of the triazine ring. The relative rates of the different hydrolysis pathways were influenced by the pK(a) of compounds. At alkaline pH, thifensulfuron methyl hydrolyzed to thifensulfuron, which was slowly transformed by cleavage of the sulfonylurea bridge and O-demethylation.

  DOI：

  10.1021/jf950194f
• 作为产物：
  描述：

  噻吩磺隆 在 pH 4 buffer 、 水 作用下， 生成 3-(4-hydroxy-6-methyl-1,3,5-triazin-2-ylcarbamoylsulfamoyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Hydrolysis Kinetics of Thifensulfuron Methyl in Aqueous Buffer Solutions

  摘要：

  The hydrolysis of thifensulfuron methyl and thifensulfuron were investigated in buffered aqueous solutions with pH values of 4, 5, 9, and 10. Hydrolysis of thifensulfuron methyl was pH dependent and relatively fast both in acidic and alkaline buffer solutions. In the case of thifensulfuron, hydrolysis rates were of the same order of magnitude as thifensulfuron methyl at acidic pH, but very low at alkaline pH. In acidic solutions, cleavage of the sulfonylurea bridge and O-demethylation of the methoxy group of the triazine ring occurred concurrently The resulting intermediates gave two parallel reactions: cleavage of the sulfonylurea bridge and opening of the triazine ring. The relative rates of the different hydrolysis pathways were influenced by the pK(a) of compounds. At alkaline pH, thifensulfuron methyl hydrolyzed to thifensulfuron, which was slowly transformed by cleavage of the sulfonylurea bridge and O-demethylation.

  DOI：

  10.1021/jf950194f

文献信息

• Hydrolysis Kinetics of Thifensulfuron Methyl in Aqueous Buffer Solutions
  作者：Jean-Pierre Cambon、Jean Bastide

  DOI：10.1021/jf950194f

  日期：1996.1.1

  The hydrolysis of thifensulfuron methyl and thifensulfuron were investigated in buffered aqueous solutions with pH values of 4, 5, 9, and 10. Hydrolysis of thifensulfuron methyl was pH dependent and relatively fast both in acidic and alkaline buffer solutions. In the case of thifensulfuron, hydrolysis rates were of the same order of magnitude as thifensulfuron methyl at acidic pH, but very low at alkaline pH. In acidic solutions, cleavage of the sulfonylurea bridge and O-demethylation of the methoxy group of the triazine ring occurred concurrently The resulting intermediates gave two parallel reactions: cleavage of the sulfonylurea bridge and opening of the triazine ring. The relative rates of the different hydrolysis pathways were influenced by the pK(a) of compounds. At alkaline pH, thifensulfuron methyl hydrolyzed to thifensulfuron, which was slowly transformed by cleavage of the sulfonylurea bridge and O-demethylation.