1H-3-bromo-4-benzylthiobenzothiopyran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异硫色烯
• 英文名称: 1H-3-bromo-4-benzylthiobenzothiopyran
• 英文别名: 4-benzylsulfanyl-3-bromo-1H-isothiochromene
• 化学式: C₁₆H₁₃BrS₂
• 分子量: 349.315
• InChiKey: HCQCDBSUPWNQJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-3-bromo-4-benzylthiobenzothiopyran 在 TrBF₄ 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以37%的产率得到1H-3-bromo-4-benzylthiobenzothiopyrylium tetrafluoroborate
  参考文献：
  名称：

  Versatile Route to Functionalized 1H-2-Benzothiopyrans and 1H-2-Naphthothiopyrans by Electrophilic Cyclization of Bis(arylmethylthio)acetylenes:  2-Benzo- and 2-Naphthothiopyrylium Salts

  摘要：

  Substituted 1H-2-benzothiopyrans find applications as pharmaceutically active compounds or synthons for more complex sulfur heterocycles. However, restricted variability in their synthesis limits the application for research or industrial purposes. To develop a direct and fast route to substituted and functionalized 1H-2-benzothiopyrans, we investigated the ring closure of symmetrical bis(arylmethylthio)acetylenes with iodine monochloride or bromine. This facile reaction yielded 1H-3-halo-4-arylmethylthio-2-benzo- and 2-naphthothiopyrans via postulated vinyl cations in yields of 47-86%. Substituted 2-benzo- and 2-naphthothiopyrylium salts were prepared by hydride abstraction with triphenylcarbenium tetrafluoroborate from the products, further enhancing the synthetic potential of the found cyclization reaction.

  DOI：

  10.1021/jo972334l
• 作为产物：
  描述：

  硫氰酸苄酯 在 氨 、 溴 、 sodium 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 0.67h， 生成 1H-3-bromo-4-benzylthiobenzothiopyran
  参考文献：
  名称：

  Versatile Route to Functionalized 1H-2-Benzothiopyrans and 1H-2-Naphthothiopyrans by Electrophilic Cyclization of Bis(arylmethylthio)acetylenes:  2-Benzo- and 2-Naphthothiopyrylium Salts

  摘要：

  Substituted 1H-2-benzothiopyrans find applications as pharmaceutically active compounds or synthons for more complex sulfur heterocycles. However, restricted variability in their synthesis limits the application for research or industrial purposes. To develop a direct and fast route to substituted and functionalized 1H-2-benzothiopyrans, we investigated the ring closure of symmetrical bis(arylmethylthio)acetylenes with iodine monochloride or bromine. This facile reaction yielded 1H-3-halo-4-arylmethylthio-2-benzo- and 2-naphthothiopyrans via postulated vinyl cations in yields of 47-86%. Substituted 2-benzo- and 2-naphthothiopyrylium salts were prepared by hydride abstraction with triphenylcarbenium tetrafluoroborate from the products, further enhancing the synthetic potential of the found cyclization reaction.

  DOI：

  10.1021/jo972334l