N,N-dimethyl-3-phenylmethoxytriazole-4-carboxamide | 198754-59-5

• 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,N-dimethyl-3-phenylmethoxytriazole-4-carboxamide
• CAS: 198754-59-5
• 化学式: C₁₂H₁₄N₄O₂
• 分子量: 246.269
• InChiKey: XXWFVOHNYIHOBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-3-phenylmethoxytriazole-4-carboxamide 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以98%的产率得到3-Hydroxy-3H-[1,2,3]triazole-4-carboxylic acid dimethylamide
  参考文献：
  名称：

  Synthesis of 5-Substituted 1-Hydroxy-1,2,3-triazoles through Directed Lithiation of 1-(Benzyloxy)-1,2,3-triazole

  摘要：

  1-(Benzyloxy)-1,2,3-triazole, prepared by selective benzylation of 1-hydroxy-1,2,3-triazole or by oxidative cyclization of 2-hydrazonoglyoxal O-benzyloxime, was metalated exclusively at the 5-position upon treatment with n-butyllithium. The anion formed reacted with a series of electrophiles. In this way carbon, halogen, sulfur, silicon, and tin substituents could be introduced at the 5-position. Subsequent removal of the benzyl group by palladium-catalyzed hydrogenolysis or by treatment with hydrochloric acid afforded the corresponding 5-substituted 1-hydroxy-1,2,3-triazoles.

  DOI：

  10.1021/jo971313o
• 作为产物：
  描述：

  Glyoxal-mono-O-benzyloxim 在 正丁基锂 、 一水合肼 、 copper(II) sulfate 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 10.08h， 生成 N,N-dimethyl-3-phenylmethoxytriazole-4-carboxamide
  参考文献：
  名称：

  Synthesis of 5-Substituted 1-Hydroxy-1,2,3-triazoles through Directed Lithiation of 1-(Benzyloxy)-1,2,3-triazole

  摘要：

  1-(Benzyloxy)-1,2,3-triazole, prepared by selective benzylation of 1-hydroxy-1,2,3-triazole or by oxidative cyclization of 2-hydrazonoglyoxal O-benzyloxime, was metalated exclusively at the 5-position upon treatment with n-butyllithium. The anion formed reacted with a series of electrophiles. In this way carbon, halogen, sulfur, silicon, and tin substituents could be introduced at the 5-position. Subsequent removal of the benzyl group by palladium-catalyzed hydrogenolysis or by treatment with hydrochloric acid afforded the corresponding 5-substituted 1-hydroxy-1,2,3-triazoles.

  DOI：

  10.1021/jo971313o

文献信息

• Synthesis of 5-Substituted 1-Hydroxy-1,2,3-triazoles through Directed Lithiation of 1-(Benzyloxy)-1,2,3-triazole
  作者：Peter Uhlmann、Jakob Felding、Per Vedsø、Mikael Begtrup

  DOI：10.1021/jo971313o

  日期：1997.12.1

  1-(Benzyloxy)-1,2,3-triazole, prepared by selective benzylation of 1-hydroxy-1,2,3-triazole or by oxidative cyclization of 2-hydrazonoglyoxal O-benzyloxime, was metalated exclusively at the 5-position upon treatment with n-butyllithium. The anion formed reacted with a series of electrophiles. In this way carbon, halogen, sulfur, silicon, and tin substituents could be introduced at the 5-position. Subsequent removal of the benzyl group by palladium-catalyzed hydrogenolysis or by treatment with hydrochloric acid afforded the corresponding 5-substituted 1-hydroxy-1,2,3-triazoles.