(+/-)-N-cyclohexyl-2-(3-hydroxy-6-oxo-5-{p-methoxyphenyl}-6H-[1,2,4]triazin-1-yl)propionamide | 898261-71-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-N-cyclohexyl-2-(3-hydroxy-6-oxo-5-{p-methoxyphenyl}-6H-[1,2,4]triazin-1-yl)propionamide
• 英文别名: N-cyclohexyl-2-[5-(4-methoxyphenyl)-3,6-dioxo-2H-1,2,4-triazin-1-yl]propanamide
• CAS: 898261-71-7
• 化学式: C₁₉H₂₄N₄O₄
• 分子量: 372.424
• InChiKey: XFLFIFUBYLWONQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 (+/-)-N-cyclohexyl-2-(3-hydroxy-6-oxo-5-{p-methoxyphenyl}-6H-[1,2,4]triazin-1-yl)propionamide 以 乙醚 、 氯仿 为溶剂， 反应 12.0h， 以86%的产率得到(+/-)-N-cyclohexyl-2-[3-methoxy-5-(4-methoxyphenyl)-6-oxo-6H-[1,2,4]triazin-1-yl]propionamide
  参考文献：
  名称：

  Synthesis of 3-Hydroxy-6-oxo[1,2,4]triazin-1-yl Alaninamides, a New Class of Cyclic Dipeptidyl Ureas

  摘要：

  Cyclohexyl or benzyl isocyanide, benzoyl-, or 4-methoxybenzoylformic acid and semicarbazones underwent Ugi reactions in methanol for 3 days to give the Ugi adducts, which were then stirred with sodium ethoxide in ethanol for 12 h to give 3-hydroxy-6-oxo[1,2,4] triazin-1-yl alaninamides. The X-ray diffraction structure of the first example showed the tautomer having the proton in the O2 atom that was fixed in the crystal by packing in dimers with a H-bond distance of 1.9 angstrom. Selected [1,2,4] triazines were treated with diazomethane for 12 h to get the O-methyl derivatives. Both hydroxy and O-methyl derivatives obtained by this method constitute a new class of pseudopeptidic [1,2,4] triazines composed of two different amino acids, arylglycine and alanine derivatives, in which the N-terminal arylglycine and the peptidic amide nitrogen atoms are bonded through a urea moiety.

  DOI：

  10.1021/jo060434y
• 作为产物：
  描述：

  对甲氧基苯乙醛酸 在 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 84.0h， 生成 (+/-)-N-cyclohexyl-2-(3-hydroxy-6-oxo-5-{p-methoxyphenyl}-6H-[1,2,4]triazin-1-yl)propionamide
  参考文献：
  名称：

  Synthesis of 3-Hydroxy-6-oxo[1,2,4]triazin-1-yl Alaninamides, a New Class of Cyclic Dipeptidyl Ureas

  摘要：

  Cyclohexyl or benzyl isocyanide, benzoyl-, or 4-methoxybenzoylformic acid and semicarbazones underwent Ugi reactions in methanol for 3 days to give the Ugi adducts, which were then stirred with sodium ethoxide in ethanol for 12 h to give 3-hydroxy-6-oxo[1,2,4] triazin-1-yl alaninamides. The X-ray diffraction structure of the first example showed the tautomer having the proton in the O2 atom that was fixed in the crystal by packing in dimers with a H-bond distance of 1.9 angstrom. Selected [1,2,4] triazines were treated with diazomethane for 12 h to get the O-methyl derivatives. Both hydroxy and O-methyl derivatives obtained by this method constitute a new class of pseudopeptidic [1,2,4] triazines composed of two different amino acids, arylglycine and alanine derivatives, in which the N-terminal arylglycine and the peptidic amide nitrogen atoms are bonded through a urea moiety.

  DOI：

  10.1021/jo060434y

文献信息

• Synthesis of 3-Hydroxy-6-oxo[1,2,4]triazin-1-yl Alaninamides, a New Class of Cyclic Dipeptidyl Ureas
  作者：María Sañudo、Stefano Marcaccini、Sara Basurto、Tomás Torroba

  DOI：10.1021/jo060434y

  日期：2006.6.1

  Cyclohexyl or benzyl isocyanide, benzoyl-, or 4-methoxybenzoylformic acid and semicarbazones underwent Ugi reactions in methanol for 3 days to give the Ugi adducts, which were then stirred with sodium ethoxide in ethanol for 12 h to give 3-hydroxy-6-oxo[1,2,4] triazin-1-yl alaninamides. The X-ray diffraction structure of the first example showed the tautomer having the proton in the O2 atom that was fixed in the crystal by packing in dimers with a H-bond distance of 1.9 angstrom. Selected [1,2,4] triazines were treated with diazomethane for 12 h to get the O-methyl derivatives. Both hydroxy and O-methyl derivatives obtained by this method constitute a new class of pseudopeptidic [1,2,4] triazines composed of two different amino acids, arylglycine and alanine derivatives, in which the N-terminal arylglycine and the peptidic amide nitrogen atoms are bonded through a urea moiety.