1-methylethyl 4-benzyl-4,5-dihydro-3-(1-methylethoxy)-5-oxo-1H-1,2,4-triazole-1-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methylethyl 4-benzyl-4,5-dihydro-3-(1-methylethoxy)-5-oxo-1H-1,2,4-triazole-1-carboxylate
• 英文别名: isopropyl 3-isopropoxy-5-oxo-4-benzyl-Δ³,1,2,4-triazoline-1-carboxylate；Propan-2-yl 4-benzyl-5-oxo-3-propan-2-yloxy-1,2,4-triazole-1-carboxylate
• 化学式: C₁₆H₂₁N₃O₄
• 分子量: 319.36
• InChiKey: IEXGYTNDCUMLKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  71.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  diisopropyl (E)-azodicarboxylate 、 异氰酸苄酯 在 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以80%的产率得到1-methylethyl 4-benzyl-4,5-dihydro-3-(1-methylethoxy)-5-oxo-1H-1,2,4-triazole-1-carboxylate
  参考文献：
  名称：

  用Mitsunobu化学合成一些新的1,2,4-三唑衍生物

  摘要：

  在三苯基膦和偶氮二羧酸二异丙酯之间的反应中产生的反应性1：1中间体已被异氰酸酯或异硫氰酸酯截留，得到1,2,4-三唑衍生物2（方案1）。高官能化化合物2的结构在光谱上得到证实（IR，1 H-和13 C-NMR，EI-MS）并通过元素分析得到证实。提出了用于这种类型的环化的机制（方案2）。

  DOI：

  10.1002/hlca.200590218

文献信息

• Preparation of Isocyanates from Primary Amines and Carbon Dioxide Using Mitsunobu Chemistry¹
  作者：Dilek Saylik、Michael J. Horvath、Patricia S. Elmes、W. Roy Jackson、Craig G. Lovel、Keith Moody

  DOI：10.1021/jo982362j

  日期：1999.5.1

  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.
• Synthesis of Some New 1,2,4-Triazole Derivatives byMitsunobu Chemistry
  作者：Abdolali Alizadeh

  DOI：10.1002/hlca.200590218

  日期：2005.10

  reactive 1 : 1 intermediate produced in the reaction between triphenylphosphine and diisopropyl azodicarboxylate has been trapped by isocyanates or isothiocyanates to yield 1,2,4-triazole derivatives 2 (Scheme 1). The structures of the highly functionalized compounds 2 were corroborated spectroscopically (IR, 1H- and 13C-NMR, EI-MS) and by elemental analyses. A mechanism for this type of cyclization

  在三苯基膦和偶氮二羧酸二异丙酯之间的反应中产生的反应性1：1中间体已被异氰酸酯或异硫氰酸酯截留，得到1,2,4-三唑衍生物2（方案1）。高官能化化合物2的结构在光谱上得到证实（IR，1 H-和13 C-NMR，EI-MS）并通过元素分析得到证实。提出了用于这种类型的环化的机制（方案2）。