6-methyl-1-(oct-1-en-2-yloxy)-1H-benzo[d][1,2,3]triazole | 1422198-30-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 6-methyl-1-(oct-1-en-2-yloxy)-1H-benzo[d][1,2,3]triazole
• 英文别名: 6-Methyl-1-oct-1-en-2-yloxybenzotriazole；6-methyl-1-oct-1-en-2-yloxybenzotriazole
• CAS: 1422198-30-8
• 化学式: C₁₅H₂₁N₃O
• 分子量: 259.351
• InChiKey: QTAVEJVKCFUKAU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-硝基-4-氯甲苯 在 三苯基膦氯金 、 silver trifluoromethanesulfonate 、 一水合肼 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 20.0h， 生成 6-methyl-1-(oct-1-en-2-yloxy)-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Gold-Catalyzed Addition of N-Hydroxy Heterocycles to Alkynes and Subsequent 3,3-Sigmatropic Rearrangement

  摘要：

  Gold-catalyzed intermolecular addition of hydroxybenzotriazole derivatives to alkynes at room temperature, gives vinyl ethers 3 in high yields and with excellent regioselectivity. Unlike many other vinyl ethers, 3 can easily be purified by regular silica-gel chromatography. On heating, 3,3-sigmatropic rearrangement of 3 gives access to highly functionalized benzotriazoles. This two-step sequence represents an efficient oxygen transfer protocol which incorporates a nucleophilic oxygen atom Into an alkyne group. Reaction of 3 with an electrophilic fluorinating reagent (Selectfluor) gives a fluorinated ketone regioselectively and in high yield.

  DOI：

  10.1021/ol4000789

文献信息

• Gold-Catalyzed Addition of <i>N</i>-Hydroxy Heterocycles to Alkynes and Subsequent 3,3-Sigmatropic Rearrangement
  作者：Manish Kumar、Martin Scobie、Mark S. Mashuta、Gerald B. Hammond、Bo Xu

  DOI：10.1021/ol4000789

  日期：2013.2.15

  Gold-catalyzed intermolecular addition of hydroxybenzotriazole derivatives to alkynes at room temperature, gives vinyl ethers 3 in high yields and with excellent regioselectivity. Unlike many other vinyl ethers, 3 can easily be purified by regular silica-gel chromatography. On heating, 3,3-sigmatropic rearrangement of 3 gives access to highly functionalized benzotriazoles. This two-step sequence represents an efficient oxygen transfer protocol which incorporates a nucleophilic oxygen atom Into an alkyne group. Reaction of 3 with an electrophilic fluorinating reagent (Selectfluor) gives a fluorinated ketone regioselectively and in high yield.