2-[(4-Methoxyphenyl)hydrazinylidene]-3-oxo-3-pyrrolidin-1-ylpropanethioamide | 896064-06-5

• 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: 2-[(4-Methoxyphenyl)hydrazinylidene]-3-oxo-3-pyrrolidin-1-ylpropanethioamide
• CAS: 896064-06-5
• 化学式: C₁₄H₁₈N₄O₂S
• 分子量: 306.389
• InChiKey: LRCWUDPNVBEKAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(4-Methoxyphenyl)hydrazinylidene]-3-oxo-3-pyrrolidin-1-ylpropanethioamide 在 溴 、 溶剂黄146 作用下， 反应 5.0h， 以63%的产率得到2-(4-methoxyphenyl)-4-(pyrrolidine-1-carbonyl)-1,2,3-thiadiazol-5(2H,5H)-iminium bromide
  参考文献：
  名称：

  Unexpected result for the acylation of arylhydrazonoethanethioamides

  摘要：

  The acylation of arylhydrazonoethanethioamides containing primary amino group did not yield acylthioamides as expected. Surprisingly, the cyclic 5-acylimino-2,5-dihydro-1,2,3-thiadiazoles were obtained. The formation of thiadiazoles in this reaction was explained by the higher ability of arylhydrazono-N-acylthioacetamide intermediates to be oxidized comparing to their precursors. The presence of pseudobicyclic aromatic structure in the reaction product was a main factor favoring the formation of 1,2,3-thiadiazole ring. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.071