1-Methyl-2,5-dioxo-4-(2-phenyl-2H-pyrazol-3-ylamino)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester | 187842-61-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-Methyl-2,5-dioxo-4-(2-phenyl-2H-pyrazol-3-ylamino)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester
• 英文别名: methyl 1-methyl-2,5-dioxo-4-[(2-phenylpyrazol-3-yl)amino]pyrrole-3-carboxylate
• CAS: 187842-61-1
• 化学式: C₁₆H₁₄N₄O₄
• 分子量: 326.312
• InChiKey: LZPSIEARKFBRPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  93.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-Methyl-2,5-dioxo-4-(2-phenyl-2H-pyrazol-3-ylamino)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester 在 一水合肼 作用下， 以 甲醇 、 二苯醚 为溶剂， 反应 0.5h， 生成 4-Hydroxy-1-phenyl-6,7-dihydro-1H-1,2,6,7,9-pentaaza-cyclopenta[b]naphthalene-5,8-dione
  参考文献：
  名称：

  Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones

  摘要：

  Reactions of 1,3-disubstituted 5-aminopyrazole-4-carboxylate derivatives (la-c) with dimethyl acetylenedicarboxylate gave the corresponding dimethyl 1,3-disubstituted 4-hydroxypyrazolo[3,4-b]pyridine-5,6-dicarboxylates (2a-c) which reacted with hydrazine hydrate to give 1,3-disubstituted 4-hydroxy-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones (3a-d). These tricyclic pyridazine derivatives were alternatively synthesized from 4-hydroxypyrrolo[3,4-e] pyrazolo[3,4-b]pyridine-5,7-diones (7a-c) prepared by reactions of 5-aminopyrazoles (1e-g) with 1-methyl-3-methylthio-4-methoxycarbonylmaleimide (5) followed by Gould-Jacacobs reaction. These tricyclic pyridazine derivatives were evaluated for chemiluminescence. 4-Hydroxy-3-methylthio-1-phenyl-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-dione (3d) showed the greatest chemiluminescence intensity in the presence of H2O2 and peroxidase in a solution of phosphate buffer at pH 10.

  DOI：

  10.3987/com-96-s17
• 作为产物：
  描述：

  5-氨基-1-苯基吡唑 、 methyl 1-methyl-4-methylthio-2,5-dioxo-3-pyrroline-3-carboxylate 以 甲醇 为溶剂， 反应 1.0h， 以82%的产率得到1-Methyl-2,5-dioxo-4-(2-phenyl-2H-pyrazol-3-ylamino)-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones

  摘要：

  Reactions of 1,3-disubstituted 5-aminopyrazole-4-carboxylate derivatives (la-c) with dimethyl acetylenedicarboxylate gave the corresponding dimethyl 1,3-disubstituted 4-hydroxypyrazolo[3,4-b]pyridine-5,6-dicarboxylates (2a-c) which reacted with hydrazine hydrate to give 1,3-disubstituted 4-hydroxy-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones (3a-d). These tricyclic pyridazine derivatives were alternatively synthesized from 4-hydroxypyrrolo[3,4-e] pyrazolo[3,4-b]pyridine-5,7-diones (7a-c) prepared by reactions of 5-aminopyrazoles (1e-g) with 1-methyl-3-methylthio-4-methoxycarbonylmaleimide (5) followed by Gould-Jacacobs reaction. These tricyclic pyridazine derivatives were evaluated for chemiluminescence. 4-Hydroxy-3-methylthio-1-phenyl-1H-pyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-dione (3d) showed the greatest chemiluminescence intensity in the presence of H2O2 and peroxidase in a solution of phosphate buffer at pH 10.

  DOI：

  10.3987/com-96-s17