2-((2-(3-nitrophenyl)-2-oxoethyl)thio)-N-(4H-1,2,4-triazol-3-yl)acetamide | 1359939-75-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-((2-(3-nitrophenyl)-2-oxoethyl)thio)-N-(4H-1,2,4-triazol-3-yl)acetamide
• 英文别名: 2-[2-(3-nitrophenyl)-2-oxoethyl]sulfanyl-N-(1H-1,2,4-triazol-5-yl)acetamide
• CAS: 1359939-75-5
• 化学式: C₁₂H₁₁N₅O₄S
• 分子量: 321.316
• InChiKey: UOEIDGYUQNMRIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  159
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 2-((2-(3-nitrophenyl)-2-oxoethyl)thio)-N-(4H-1,2,4-triazol-3-yl)acetamide 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以40%的产率得到6-(3-nitrobenzoyl)-4-(4H-1,2,4-triazol-3-yl)thiomorpholin-3-one
  参考文献：
  名称：

  A chemoselective hydroxymethylation: new route for the synthesis of 6-aroyl-4-(4H-triazol-3-yl)thiomorpholin-3-ones

  摘要：

  Treatment of 2-(2-oxo-2-arylethylthio)-N-(4H-1,2,4-triazol-3-yl)acetamides with paraformaldehyde in the presence of a base has led to a tandem chemoselective hydroxymethylation followed by cyclization yielding a set of novel 6-aroyl-4-(4H-triazol-3-yl)thiomorpholin-3-ones. The thiomorpholine ring has been found to have a boat like conformation in these compounds as evidenced by NOESY NMR spectrum. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.100
• 作为产物：
  描述：

  2-mercapto-N-(4H-1,2,4-triazol-3-yl)acetamide 、 2-溴-3'-硝基苯乙酮 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 2-((2-(3-nitrophenyl)-2-oxoethyl)thio)-N-(4H-1,2,4-triazol-3-yl)acetamide
  参考文献：
  名称：

  具有生物重要性的N-杂芳基-2-（杂芳硫基）乙酰胺的合成

  摘要：

  已经描述了具有通过连接中具有硫和氮的链连接的三唑和selena /噻二唑环的化合物的合成。所得的N-杂芳基-2-（杂芳硫基）乙酰胺可能具有重要的生物学意义，因为相关化合物可用于抑制HIV 1复制。

  DOI：

  10.1002/jhet.1804

文献信息

• Synthesis of Quinolines Linked to Triazoles Through Sulfur
  作者：Thulasiraman Krishnaraj、Shanmugam Muthusubramanian

  DOI：10.1002/jhet.2149

  日期：2015.3

  The article summarizes the synthesis of two heterocycles linked by sulfur atom. The Friedlander reactions of 2‐aminoarylketones with ketones 1, 4, and 7 have been explored, and three series of quinolines (3, 5, and 8) have been synthesized.

  该文章总结了由硫原子连接的两个杂环的合成。的2-氨基芳香与酮的反应弗里德兰德1，4，和7已探索，以及三个系列喹啉（的3，5，和8）已经被合成。
• A chemoselective hydroxymethylation: new route for the synthesis of 6-aroyl-4-(4H-triazol-3-yl)thiomorpholin-3-ones
  作者：Thulasiraman Krishnaraj、Shanmugam Muthusubramanian

  DOI：10.1016/j.tetlet.2011.12.100

  日期：2012.2

  Treatment of 2-(2-oxo-2-arylethylthio)-N-(4H-1,2,4-triazol-3-yl)acetamides with paraformaldehyde in the presence of a base has led to a tandem chemoselective hydroxymethylation followed by cyclization yielding a set of novel 6-aroyl-4-(4H-triazol-3-yl)thiomorpholin-3-ones. The thiomorpholine ring has been found to have a boat like conformation in these compounds as evidenced by NOESY NMR spectrum. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of Biologically Important<i>N</i>-Heteroaryl-2-(heteroarylthio)acetamides
  作者：Thulasiraman Krishnaraj、Shanmugam Muthusubramanian

  DOI：10.1002/jhet.1804

  日期：2014.7

  The synthesis of compounds having triazole and selena/thiadiazole rings connected by a chain having sulfur and nitrogen in the link has been described. The resultant N‐heteroaryl‐2‐(heteroarylthio)acetamide may be biologically important as related compounds found application in the inhibition of HIV 1 replications.

  已经描述了具有通过连接中具有硫和氮的链连接的三唑和selena /噻二唑环的化合物的合成。所得的N-杂芳基-2-（杂芳硫基）乙酰胺可能具有重要的生物学意义，因为相关化合物可用于抑制HIV 1复制。