1-benzyloxy-1,2,3-triazole | 26957-01-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-benzyloxy-1,2,3-triazole
• 英文别名: 1-benzyloxy-1H-[1,2,3]triazole；1-(benzyloxy)-1H-1,2,3-triazole；1-phenylmethoxytriazole
• CAS: 26957-01-7
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: ZQRIUOKEGQKRKF-UHFFFAOYSA-N

物化性质

• 沸点：
  308.6±35.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-1,2,3-triazole 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以96%的产率得到1-hydroxy-1,2,3-triazole
  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：

  在 copper(II) sulfate 作用下， 以 吡啶 为溶剂， 反应 0.5h， 生成 1-benzyloxy-1,2,3-triazole
  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 novel azaxanthones derived from N-hydroxyazoles
  作者：Jesper L Kristensen、Per Vedsø、Mikael Begtrup

  DOI：10.1016/s0040-4020(02)00034-0

  日期：2002.3

  The synthesis of a new class of azaxanthones is presented. The N-O functionality of 1-hydroxypyrazole and 1-hydroxy-1,2,3-triazole was used to direct metalation and subsequently incorporated in the new ring systems. (C) 2002 Published by Elsevier Science Ltd.
• Begtup, Mikael; Jonsson, Gujion, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1987, vol. 41, # 10, p. 724 - 735
  作者：Begtup, Mikael、Jonsson, Gujion

  DOI：——

  日期：——
• Palladium-Catalyzed Arylation and Acylation of 1-Benzyloxy-1,2,3-triazole Through a Directed Ortho Lithiation-Transmetalation Strategy
  作者：Jakob Felding、Peter Uhlmann、Jesper Kristensen、Per Vedsø、Mikael Begtrup

  DOI：10.1055/s-1998-2131

  日期：1998.8
• BEGTRUP, MIKAEL;JONSSON, GUDJON, ACTA CHEM. SCAND., 41,(1987) N 10, 724-735
  作者：BEGTRUP, MIKAEL、JONSSON, GUDJON

  DOI：——

  日期：——
• 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.