2-ethoxycarbonylmethylthio-6-ethylthieno[2,3-d]pyrimidine-4-one | 1240065-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 2-ethoxycarbonylmethylthio-6-ethylthieno[2,3-d]pyrimidine-4-one
• 英文别名: ethyl 2-[(6-ethyl-4-oxo-3H-thieno[2,3-d]pyrimidin-2-yl)sulfanyl]acetate
• CAS: 1240065-15-9
• 化学式: C₁₂H₁₄N₂O₃S₂
• 分子量: 298.387
• InChiKey: SBACTKUEXYNSOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-ethyl-2-thioxo-2,3-dihydrothieno[2,3-d]pyrimidin-4(1H)-one 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以70%的产率得到2-ethoxycarbonylmethylthio-6-ethylthieno[2,3-d]pyrimidine-4-one
  参考文献：
  名称：

  Synthesis and Biological Activity of a Series of New Thieno[2,3-d]Pyrimidines

  摘要：

  Ethyl 2-amino-5-ethylthiophene-3- carboxylate 1, obtained from the reaction of butyraldehyde, ethyl cyanoacetate, sulfur, and triethylamine, reacted with benzoylisothiocyanate to give the corresponding ureido derivatives 2 in a high yield. Further reactions of the compound 2 with an aqueous-alcohol solution of potassium hydroxide and then with hydrochloric acid gave the 2-thio-thieno[2,3-d]pyrimidine-4-ones 3, which were reacted with RX to give novel compounds 4a-4i. Treating the compound 3 with dibromoalkane led to the formation of triacylic compounds 5j-5m. Their structures were clearly verified by IR, 1H NMR, EI-MS spectroscopy, and elemental analysis. The results of a preliminary bioassay indicated that some compounds possess excellent inhibitory activities against the root and the stalk of Brassica napus (rape) and Echinochloa crusgalli (barnyard grass) at a dosage of 100 mg/L. 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：

  10.1080/10426500903127565

文献信息

• Synthesis and Biological Activity of a Series of New Thieno[2,3-d]Pyrimidines
  作者：Tao Wang、Cai Hua Zheng、Sue Liu、Hui Zong Chen

  DOI：10.1080/10426500903127565

  日期：2010.6.30

  Ethyl 2-amino-5-ethylthiophene-3- carboxylate 1, obtained from the reaction of butyraldehyde, ethyl cyanoacetate, sulfur, and triethylamine, reacted with benzoylisothiocyanate to give the corresponding ureido derivatives 2 in a high yield. Further reactions of the compound 2 with an aqueous-alcohol solution of potassium hydroxide and then with hydrochloric acid gave the 2-thio-thieno[2,3-d]pyrimidine-4-ones 3, which were reacted with RX to give novel compounds 4a-4i. Treating the compound 3 with dibromoalkane led to the formation of triacylic compounds 5j-5m. Their structures were clearly verified by IR, 1H NMR, EI-MS spectroscopy, and elemental analysis. The results of a preliminary bioassay indicated that some compounds possess excellent inhibitory activities against the root and the stalk of Brassica napus (rape) and Echinochloa crusgalli (barnyard grass) at a dosage of 100 mg/L. 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.