5-Amino-3-methylsulfanyl-1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid methyl ester | 187842-55-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-Amino-3-methylsulfanyl-1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid methyl ester
• 英文别名: Methyl 5-amino-1-(4-methylphenyl)sulfonyl-3-methylsulfanylpyrazole-4-carboxylate
• CAS: 187842-55-3
• 化学式: C₁₃H₁₅N₃O₄S₂
• 分子量: 341.412
• InChiKey: ZCFRAXMHCRFESF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  138
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-Amino-3-methylsulfanyl-1-(toluene-4-sulfonyl)-1H-pyrazole-4-carboxylic acid methyl ester 在 potassium carbonate 、 一水合肼 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 20.0h， 生成 4-hydroxy-3-methylthiopyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8-(6H,7H)-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：

  2-氰-3,3-二(甲硫基)丙烯酸甲酯 、 对甲苯磺酰肼 以 甲醇 为溶剂， 以73%的产率得到5-Amino-3-methylsulfanyl-1-(toluene-4-sulfonyl)-1H-pyrazole-4-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

文献信息

• Synthesis and Chemiluminescence of 1,3-Disubstituted 4-Hydroxypyrazolo[4',3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones
  作者：Yoshinori Tominaga、Noriko Yoshioka、Hiroki Minematsu、Seigo Kataoka

  DOI：10.3987/com-96-s17

  日期：——

  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.