5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole-4-carbaldehyde | 370590-46-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole-4-carbaldehyde
• 英文别名: 5-(2,6-Dimethylmorpholin-4-yl)-1,2,3-thiadiazole-4-carbaldehyde；5-(2,6-dimethylmorpholin-4-yl)thiadiazole-4-carbaldehyde
• CAS: 370590-46-8
• 化学式: C₉H₁₃N₃O₂S
• mdl: MFCD06242442
• 分子量: 227.287
• InChiKey: FMTQWUPNRIMQPF-UHFFFAOYSA-N

物化性质

• 沸点：
  377.9±52.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  83.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole-4-carbaldehyde 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以77%的产率得到5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole
  参考文献：
  名称：

  Reactions of 5-dialkylamino-1,2,3-thiadiazole-4-carbaldehydes with amines as a method for the synthesis of 1,2,3-triazole-4-carbothioamides

  摘要：

  A method for the synthesis of previously inaccessible 5-dialkylamino-substituted 1,2,3-thiadiazole-4-carbaldehydes was developed. Ring transformation in these compounds induced by primary aliphatic and aromatic amines, hydroxylamines, and N-substituted hydrazines resulted in the synthesis of a broad range of 1,2,3-triazole-4-carbothioamide.

  DOI：

  10.1023/b:rucb.0000042292.19119.3d
• 作为产物：
  描述：

  4-hydroxymethyl-5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以53%的产率得到5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole-4-carbaldehyde
  参考文献：
  名称：

  摘要：

  The method for the synthesis of 5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole-4-carbaldehyde was proposed. Its reaction with sodium 1-amino-4-(N-methyl)carbamoyl- 1,2,3-triazol-5-olate proceeds through a tandem of the Cornforth rearrangements. The initially formed azomethine isomerizes into sodium 4'-(2,6-dimethylmorpholino)thiocarbonyl-4-(N-methyl)carbamoyl- 1,1'-bis[1,2,3]triazolyl-5-olate, which then rearranges to give sodium 4-{N-{4-(2,6-dimethylmorpholinothiocarbonyl)-1,2,3-triazol-1-yl]carbamoyl}-1-methyl-1,2,3-triazol-5-olate.

  DOI：

  10.1023/a:1009582402351

文献信息

• 3-(4-Thiocarbamoyl-1,2,3-triazol-1-yl)benzo-15-crown-5: synthesis and properties
  作者：P. E. Prokhorova、T. V. Glukhareva、L. V. Dyudya、E. A. Alekseeva、Yu. Yu. Morzherin

  DOI：10.1007/s11172-010-0177-1

  日期：2010.4

  A reaction of 1,2,3-thiadiazole-4-carbaldehyde with 3-aminobenzo-15-crown-5 involves the Cornforth rearrangement of the 1,2,3-thiadiazole ring, which leads to 1,2,3-triazole-4-carbothioamide containing the benzocrown ether substituent in position 1 of the triazole ring. Reversible formation of the isomeric thiadiazole occurs in aprotic nonpolar solvents such as deuterated chloroform. These compounds

  1,2,3-噻二唑-4-甲醛与 3-氨基苯并-15-冠-5 的反应涉及 1,2,3-噻二唑环的 Cornforth 重排，这导致 1,2,3-三唑-在三唑环的 1 位含有苯并冠醚取代基的 4-硫代碳酰胺。异构噻二唑的可逆形成发生在非质子非极性溶剂如氘代氯仿中。这些化合物适用于从水相中提取 α-氨基酸。
• ——
  作者：T. V. Glukhareva、Yu. Yu. Morzherin、E. A. Savel"eva、Yu. A. Rozin、A. V. Tkachev、V. A. Bakulev

  DOI：10.1023/a:1009582402351

  日期：——

  The method for the synthesis of 5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole-4-carbaldehyde was proposed. Its reaction with sodium 1-amino-4-(N-methyl)carbamoyl- 1,2,3-triazol-5-olate proceeds through a tandem of the Cornforth rearrangements. The initially formed azomethine isomerizes into sodium 4'-(2,6-dimethylmorpholino)thiocarbonyl-4-(N-methyl)carbamoyl- 1,1'-bis[1,2,3]triazolyl-5-olate, which then rearranges to give sodium 4-N-4-(2,6-dimethylmorpholinothiocarbonyl)-1,2,3-triazol-1-yl]carbamoyl}-1-methyl-1,2,3-triazol-5-olate.
• Reactions of 5-dialkylamino-1,2,3-thiadiazole-4-carbaldehydes with amines as a method for the synthesis of 1,2,3-triazole-4-carbothioamides
  作者：T. V. Glukhareva、Yu. Yu. Morzherin、L. V. Dyudya、K. V. Malysheva、A. V. Tkachev、A. Padva、V. A. Bakulev

  DOI：10.1023/b:rucb.0000042292.19119.3d

  日期：2004.6

  A method for the synthesis of previously inaccessible 5-dialkylamino-substituted 1,2,3-thiadiazole-4-carbaldehydes was developed. Ring transformation in these compounds induced by primary aliphatic and aromatic amines, hydroxylamines, and N-substituted hydrazines resulted in the synthesis of a broad range of 1,2,3-triazole-4-carbothioamide.