5-[(chloromethyl)thio]-1-phenyl-1H-tetrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-[(chloromethyl)thio]-1-phenyl-1H-tetrazole
• 英文别名: 5-(Chloromethylsulfanyl)-1-phenyltetrazole
• 化学式: C₈H₇ClN₄S
• 分子量: 226.689
• InChiKey: UHLZYOFBISYKRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-[(chloromethyl)thio]-1-phenyl-1H-tetrazole 在 potassium fluoride 、 sodium azide 、 18-冠醚-6 、 hexaammonium heptamolybdate tetrahydrate 、 双氧水 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 29.0h， 生成 1-{[(1-phenyl-1H-tetrazol-5-yl)sulfonyl]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
• 作为产物：
  描述：

  溴氯甲烷 、 1-苯基-5-巯基四氮唑 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以70%的产率得到5-[(chloromethyl)thio]-1-phenyl-1H-tetrazole
  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

• Stereoselective Synthesis of <i>Z</i> Alkenyl Halides via Julia Olefination
  作者：Marie-Eve Lebrun、Paul Le Marquand、Carl Berthelette

  DOI：10.1021/jo052370h

  日期：2006.3.1

  Julia olefination between alpha-halomethyl sulfones and a variety of aldehydes afforded alkenyl halides in good to excellent yields with high E/Z stereo selectivities. Sulfones were readily prepared in two or three steps from commercially available reagents in good yields. Optimization revealed that the nature of the Z solvent, the base, and the additive were crucial to obtain the desired alkenyl halides.
• US5455222A
  申请人：——

  公开号：US5455222A

  公开（公告）日：1995-10-03
• 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.