5-[1-(4-Fluorophenyl)ethylsulfanyl]-1-phenyltetrazole | 852558-64-6

• 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-[1-(4-Fluorophenyl)ethylsulfanyl]-1-phenyltetrazole
• CAS: 852558-64-6
• 化学式: C₁₅H₁₃FN₄S
• 分子量: 300.359
• InChiKey: BYKAMBZEIMQTEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  68.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 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 5-[1-(4-Fluorophenyl)ethylsulfanyl]-1-phenyltetrazole
  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

• Ga(OTf)₃-Catalyzed Direct Substitution of Alcohols with Sulfur Nucleophiles
  作者：Xinping Han、Jimmy Wu

  DOI：10.1021/ol102565b

  日期：2010.12.17

  It is reported that Ga(OTf)(3) catalyzes the direct displacement of alcohols with sulfur nucleophiles. The products are versatile intermediates that can be utilized in carbon carbon, carbon sulfur bond formation or used in modified Julia olefination reactions. The only byproduct generated is water.
• C(sp3)–H (N‐Phenyltetrazole)thiolation as an Enabling Tool for Molecular Diversification
  作者：Ashley Zachmann、Justine Drappeau、Shubin Liu、Erik John Alexanian

  DOI：10.1002/anie.202404879

  日期：——

  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.