1-{[(1-phenyl-1H-tetrazol-5-yl)thio]methyl}-1H-benzo[d][1,2,3]triazole | 874767-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-{[(1-phenyl-1H-tetrazol-5-yl)thio]methyl}-1H-benzo[d][1,2,3]triazole
• 英文别名: 1-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}-1H-benzotriazole；1-[(1-phenyltetrazol-5-yl)sulfanylmethyl]benzotriazole
• CAS: 874767-35-8
• 化学式: C₁₄H₁₁N₇S
• 分子量: 309.354
• InChiKey: JAXZRJVOGNKSPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  99.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 20.5h， 生成 (Z)-1-(non-1-enyl)-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
• 作为产物：
  描述：

  1-苯基-5-巯基四氮唑 在 potassium fluoride 、 sodium azide 、 18-冠醚-6 、 potassium carbonate 、 sodium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 12.0h， 生成 1-{[(1-phenyl-1H-tetrazol-5-yl)thio]methyl}-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