isopropyl 3-isopropoxy-5-oxo-4-(3-nitrophenyl)-Δ³,1,2,4-triazoline-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: isopropyl 3-isopropoxy-5-oxo-4-(3-nitrophenyl)-Δ³,1,2,4-triazoline-1-carboxylate
• 英文别名: Propan-2-yl 4-(3-nitrophenyl)-5-oxo-3-propan-2-yloxy-1,2,4-triazole-1-carboxylate
• 化学式: C₁₅H₁₈N₄O₆
• 分子量: 350.331
• InChiKey: QULBRHWTLLMZKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  二氧化碳 、 偶氮二甲酸二异丙酯 、 间硝基苯胺 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、101.32 kPa 条件下， 以100%的产率得到isopropyl 3-isopropoxy-5-oxo-4-(3-nitrophenyl)-Δ³,1,2,4-triazoline-1-carboxylate
  参考文献：
  名称：

  Preparation of Isocyanates from Primary Amines and Carbon Dioxide Using Mitsunobu Chemistry¹

  摘要：

  Primary alkylamines 1 and hindered arylamines 1 give high yields of isocyanates 5 when reacted with carbon dioxide and the Mitsunobu zwitterions 4 generated from dialkyl azodicarboxylates and Bu3P in dichloromethane at -78 degrees C. Use of Ph3P still gave high yields of isocyanates from reactions of primary alkylamines, but only low yields were obtained from reactions of aromatic amines. Reactions which failed to give high yields of isocyanates gave either carbamoylhydrazines 6 and/or dicarbamoylhydrazines 10 and/or triazolinones 7. The triazolinones were shown to arise from reactions of reactive aryl isocyanates with the Mitsunobu zwitterion. The carbamoylhydrazines were shown not to arise from reaction, of isocyanate with reduced dialkyl azodicarboxylates, and a mechanism for their formation is proposed. Single-crystal X-ray analyses confirmed the structures of 6, 7, and 10.

  DOI：

  10.1021/jo982362j