N-cyclohexyl-1-[N'-carbamoyl-N-(2-oxo-2-{p-methoxyphenyl}acetyl)hydrazino]cyclohexanecarboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-cyclohexyl-1-[N'-carbamoyl-N-(2-oxo-2-{p-methoxyphenyl}acetyl)hydrazino]cyclohexanecarboxamide
• 英文别名: 1-[(carbamoylamino)-[2-(4-methoxyphenyl)-2-oxoacetyl]amino]-N-cyclohexylcyclohexane-1-carboxamide
• 化学式: C₂₃H₃₂N₄O₅
• 分子量: 444.531
• InChiKey: QPDNURKELHOVTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  131
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-cyclohexyl-1-[N'-carbamoyl-N-(2-oxo-2-{p-methoxyphenyl}acetyl)hydrazino]cyclohexanecarboxamide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以54%的产率得到N-cyclohexyl-1-(3-hydroxy-6-oxo-5-{p-methoxyphenyl}-6H-[1,2,4]triazin-1-yl)cyclohexanecarboxamide
  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：

  异氰环已烷 、 环己醛缩氨基脲 、 对甲氧基苯乙醛酸 以 甲醇 为溶剂， 反应 72.0h， 以73%的产率得到N-cyclohexyl-1-[N'-carbamoyl-N-(2-oxo-2-{p-methoxyphenyl}acetyl)hydrazino]cyclohexanecarboxamide
  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.