1-phenyl-5-((1-(p-tolyl)ethyl)thio)-1H-tetrazole | 127866-71-1

• 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-phenyl-5-((1-(p-tolyl)ethyl)thio)-1H-tetrazole
• 英文别名: 1-Phenyl-5-(1-p-tolyl-ethylsulfanyl)-1H-tetrazole；5-[1-(4-methylphenyl)ethylsulfanyl]-1-phenyltetrazole
• CAS: 127866-71-1
• 化学式: C₁₆H₁₆N₄S
• 分子量: 296.396
• InChiKey: SQSCHJLLTKJLNK-UHFFFAOYSA-N

物化性质

• 沸点：
  470.3±48.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-5-((1-(p-tolyl)ethyl)thio)-1H-tetrazole 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以60 %的产率得到1-phenyl-5-((1-(p-tolyl)ethyl)sulfonyl)-1H-tetrazole
  参考文献：
  名称：

  C(sp3)−H (N‐Phenyltetrazole)thiolation as an Enabling Tool for Molecular Diversification

  摘要：

  Methods enabling the broad diversification of C(sp3)–H bonds from a common intermediate are especially valuable in chemical synthesis. Herein, we report a site‐selective (N‐phenyltetrazole)thiolation of aliphatic and (hetero)benzylic C(sp3)–H bonds using a commercially available disulfide to access N‐phenyltetrazole thioethers. The thioether products are readily elaborated in diverse fragment couplings for C–C, C–O, or C–N construction. The C–H functionalization proceeds via a radical‐chain pathway involving hydrogen atom transfer by the electron‐poor N‐phenyltetrazolethiyl radical. Hexafluoroisopropanol was found to be essential to reactions involving aliphatic C(sp3)–H thiolation, with computational analysis consistent with dual hydrogen bonding of the N‐phenyltetrazolethiyl radical imparting increased radical electrophilicity to facilitate the hydrogen atom transfer. Substrate is limiting reagent in all cases, and the reaction displays an exceptional functional group tolerance well suited to applications in late‐stage diversification.

  DOI：

  10.1002/anie.202404879
• 作为产物：
  描述：

  1-苯基-5-巯基四氮唑 在 双氧水 、 溶剂红 43 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 24.17h， 生成 1-phenyl-5-((1-(p-tolyl)ethyl)thio)-1H-tetrazole
  参考文献：
  名称：

  C(sp3)−H (N‐Phenyltetrazole)thiolation as an Enabling Tool for Molecular Diversification

  摘要：

  Methods enabling the broad diversification of C(sp3)–H bonds from a common intermediate are especially valuable in chemical synthesis. Herein, we report a site‐selective (N‐phenyltetrazole)thiolation of aliphatic and (hetero)benzylic C(sp3)–H bonds using a commercially available disulfide to access N‐phenyltetrazole thioethers. The thioether products are readily elaborated in diverse fragment couplings for C–C, C–O, or C–N construction. The C–H functionalization proceeds via a radical‐chain pathway involving hydrogen atom transfer by the electron‐poor N‐phenyltetrazolethiyl radical. Hexafluoroisopropanol was found to be essential to reactions involving aliphatic C(sp3)–H thiolation, with computational analysis consistent with dual hydrogen bonding of the N‐phenyltetrazolethiyl radical imparting increased radical electrophilicity to facilitate the hydrogen atom transfer. Substrate is limiting reagent in all cases, and the reaction displays an exceptional functional group tolerance well suited to applications in late‐stage diversification.

  DOI：

  10.1002/anie.202404879

文献信息

• Silver triflate-promoted coupling reactions of benzylic and allylic sulfides with -silylated enolates of ketones and esters, a synthesis of (±)--turmerone
  作者：Kazuyoshi Takeda、Katsumi Torii、Haruo Ogura

  DOI：10.1016/s0040-4039(00)94388-0

  日期：1990.1
• TAKEDA, KAZUYOSHI;TARII, KATSUMI;OGURA, HARUO, TETRAHEDRON LETT., 31,(1990) N, C. 265-266
  作者：TAKEDA, KAZUYOSHI、TARII, KATSUMI、OGURA, HARUO

  DOI：——

  日期：——