(E)-1-[2-(thiophen-2-yl)vinyl]-1H-benzo[d][1,2,3]triazole | 769967-55-7

• 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: (E)-1-[2-(thiophen-2-yl)vinyl]-1H-benzo[d][1,2,3]triazole
• 英文别名: 1-[(E)-2-thiophen-2-ylethenyl]benzotriazole
• CAS: 769967-55-7
• 化学式: C₁₂H₉N₃S
• 分子量: 227.29
• InChiKey: FIMGEKLGKRESFA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-{[(1-phenyl-1H-tetrazol-5-yl)thio]methyl}-1H-benzo[d][1,2,3]triazole 在 hexaammonium heptamolybdate tetrahydrate 、 双氧水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 25.0h， 生成 (E)-1-[2-(thiophen-2-yl)vinyl]-1H-benzo[d][1,2,3]triazole 、 (Z)-1-[2-(thiophen-2-yl)vinyl]-1H-benzo[d][1,2,3]triazole
  参考文献：
  名称：

  Modular Synthesis of N-Vinyl Benzotriazoles

  摘要：

  A modular approach to N1-vinyl benzotriazoles by azide-aryne cycloadditions and Julia-Kocienski reactions is described. Reactions of azidomethyl phenyl-1H-tetrazol-5-yl (PT) sulfide with arynes gave methyl(PT-sulfanyl)-substituted benzotriazoles in 68-89% yields. Oxidation of the sulfides to the sulfones gave the benzotriazole-substituted Julia-Kocienski reagents. Olefination reactions of aldehydes and a ketone with reagents derived from benzyne, 2,3-naphthyne, and 4,5-dimethoxybenzyne precursors proceeded to give various NI-vinyl benzotriazole derivatives. Olefination stereoselectivities are tunable for electron-rich aldehydes, but not for electron-deficient aldehydes and alkanals, where they proceed with good to excellent Z-stereoselectivity.

  DOI：

  10.1021/ol401661j

文献信息

• Modular Synthesis of <i>N</i>-Vinyl Benzotriazoles
  作者：Govindra Singh、Rakesh Kumar、Jorge Swett、Barbara Zajc

  DOI：10.1021/ol401661j

  日期：2013.8.16

  A modular approach to N1-vinyl benzotriazoles by azide-aryne cycloadditions and Julia-Kocienski reactions is described. Reactions of azidomethyl phenyl-1H-tetrazol-5-yl (PT) sulfide with arynes gave methyl(PT-sulfanyl)-substituted benzotriazoles in 68-89% yields. Oxidation of the sulfides to the sulfones gave the benzotriazole-substituted Julia-Kocienski reagents. Olefination reactions of aldehydes and a ketone with reagents derived from benzyne, 2,3-naphthyne, and 4,5-dimethoxybenzyne precursors proceeded to give various NI-vinyl benzotriazole derivatives. Olefination stereoselectivities are tunable for electron-rich aldehydes, but not for electron-deficient aldehydes and alkanals, where they proceed with good to excellent Z-stereoselectivity.