3-ethoxycarbonyl-4-methyl-5-phenyl-thien-2-ylazomalononitrile | 1240035-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 3-ethoxycarbonyl-4-methyl-5-phenyl-thien-2-ylazomalononitrile
• 英文别名: Ethyl 2-(dicyanomethyldiazenyl)-4-methyl-5-phenylthiophene-3-carboxylate
• CAS: 1240035-25-9
• 化学式: C₁₇H₁₄N₄O₂S
• 分子量: 338.39
• InChiKey: NMMSTTWJSXRHPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  127
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-ethoxycarbonyl-4-methyl-5-phenyl-thien-2-ylazomalononitrile 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以80%的产率得到3,3-dicyano-5-methyl-6-phenylthieno[2,3-c]pyridazine-4-one
  参考文献：
  名称：

  An Efficient Synthesis of New Substituted Spiro Pyrazolethieno, Pyrimidinethieno, and Benzodiazepinethieno Pyridazine Derivatives with Biological Activities

  摘要：

  3-Ethyl 2-amino-4-methyl-5-phenyl thiophene carboxylate 1 was used as a starting material to synthesize 2a,b via coupling with malononitrile or acetyl acetone, respectively. When heated, under reflux in sodium ethoxide solution, 2a,b give 3a,b. On the other hand, when compounds 3a,b were heated under reflux in ethanol with hydrazine hydrate, thiourea, or 1,1-phenylenediamine hydrochloride and a catalytic amount of piperidine 4a,b, 5a,b and 6a,b, were produced, respectively. The new compounds were tested for their antimicrobial activity. Compounds 2a-6b showed antibacterial activities, and 2a,2b and 4b showed antifungal activities. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903095531
• 作为产物：
  描述：

  2-氨基-4-甲基-5-苯基噻吩-3-羧酸乙酯 、 丙二腈 在 磷酸 、 溶剂黄146 、 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 以80%的产率得到3-ethoxycarbonyl-4-methyl-5-phenyl-thien-2-ylazomalononitrile
  参考文献：
  名称：

  An Efficient Synthesis of New Substituted Spiro Pyrazolethieno, Pyrimidinethieno, and Benzodiazepinethieno Pyridazine Derivatives with Biological Activities

  摘要：

  3-Ethyl 2-amino-4-methyl-5-phenyl thiophene carboxylate 1 was used as a starting material to synthesize 2a,b via coupling with malononitrile or acetyl acetone, respectively. When heated, under reflux in sodium ethoxide solution, 2a,b give 3a,b. On the other hand, when compounds 3a,b were heated under reflux in ethanol with hydrazine hydrate, thiourea, or 1,1-phenylenediamine hydrochloride and a catalytic amount of piperidine 4a,b, 5a,b and 6a,b, were produced, respectively. The new compounds were tested for their antimicrobial activity. Compounds 2a-6b showed antibacterial activities, and 2a,2b and 4b showed antifungal activities. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

  DOI：

  10.1080/10426500903095531

文献信息

• An Efficient Synthesis of New Substituted Spiro Pyrazolethieno, Pyrimidinethieno, and Benzodiazepinethieno Pyridazine Derivatives with Biological Activities
  作者：Rasha A. M. Faty、Hoda A. R. Hussein、Ayman M. S. Youssef

  DOI：10.1080/10426500903095531

  日期：2010.6.30

  3-Ethyl 2-amino-4-methyl-5-phenyl thiophene carboxylate 1 was used as a starting material to synthesize 2a,b via coupling with malononitrile or acetyl acetone, respectively. When heated, under reflux in sodium ethoxide solution, 2a,b give 3a,b. On the other hand, when compounds 3a,b were heated under reflux in ethanol with hydrazine hydrate, thiourea, or 1,1-phenylenediamine hydrochloride and a catalytic amount of piperidine 4a,b, 5a,b and 6a,b, were produced, respectively. The new compounds were tested for their antimicrobial activity. Compounds 2a-6b showed antibacterial activities, and 2a,2b and 4b showed antifungal activities. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.