N-[(4-methoxyphenyl)methylcarbamoylamino]formamide | 819803-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-[(4-methoxyphenyl)methylcarbamoylamino]formamide
• CAS: 819803-51-5
• 化学式: C₁₀H₁₃N₃O₃
• 分子量: 223.232
• InChiKey: ZBJALSKDZMXXBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  79.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(4-methoxyphenyl)methylcarbamoylamino]formamide 在 硫酸氢铵 、 三甲基溴硅烷 、 六甲基二硅氮烷 作用下， 反应 30.0h， 以90%的产率得到4-[(4-methoxyphenyl)methyl]-1H-1,2,4-triazol-5-one
  参考文献：
  名称：

  Manipulation of N,O-Nucleophilicity:  Efficient Formation of 4-N-Substituted 2,4-Dihydro-3H-1,2,4-Triazolin-3-ones

  摘要：

  A new efficient two-step synthesis of 2,4-dihydro-3H-1,2,4-triazolin-3-ones (triazolinones) from readily available amines is reported. Our novel conditions using hexamethyl disilazane, bromotrimethylsilane, and a catalytic amount of ammonium sulfate smoothly cyclize 1-formyl and 1-acetyl semicarbazides to the target triazolinones. This transformation features simultaneous manipulation of N- and O-nucleophilicity as well as differentiation of the nucleophilicity of a urea and an acyl carbonyl.

  DOI：

  10.1021/ol0478638
• 作为产物：
  描述：

  甲酰肼 、 4-甲氧苄基异氰酸酯 以 乙腈 为溶剂， 反应 4.0h， 以0.40 g的产率得到N-[(4-methoxyphenyl)methylcarbamoylamino]formamide
  参考文献：
  名称：

  Manipulation of N,O-Nucleophilicity:  Efficient Formation of 4-N-Substituted 2,4-Dihydro-3H-1,2,4-Triazolin-3-ones

  摘要：

  A new efficient two-step synthesis of 2,4-dihydro-3H-1,2,4-triazolin-3-ones (triazolinones) from readily available amines is reported. Our novel conditions using hexamethyl disilazane, bromotrimethylsilane, and a catalytic amount of ammonium sulfate smoothly cyclize 1-formyl and 1-acetyl semicarbazides to the target triazolinones. This transformation features simultaneous manipulation of N- and O-nucleophilicity as well as differentiation of the nucleophilicity of a urea and an acyl carbonyl.

  DOI：

  10.1021/ol0478638

文献信息

• Manipulation of N,O-Nucleophilicity:  Efficient Formation of 4-N-Substituted 2,4-Dihydro-3<i>H</i>-1,2,4-Triazolin-3-ones
  作者：Xianhai Huang、Anandan Palani、Dong Xiao、Robert Aslanian、Neng-Yang Shih

  DOI：10.1021/ol0478638

  日期：2004.12.1

  A new efficient two-step synthesis of 2,4-dihydro-3H-1,2,4-triazolin-3-ones (triazolinones) from readily available amines is reported. Our novel conditions using hexamethyl disilazane, bromotrimethylsilane, and a catalytic amount of ammonium sulfate smoothly cyclize 1-formyl and 1-acetyl semicarbazides to the target triazolinones. This transformation features simultaneous manipulation of N- and O-nucleophilicity as well as differentiation of the nucleophilicity of a urea and an acyl carbonyl.