10,10,11,11-Tetramethyl-12-(4-methylphenyl)-9-thia-12-azatricyclo[6.3.1.02,7]dodeca-2,4,6-triene | 141663-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 10,10,11,11-Tetramethyl-12-(4-methylphenyl)-9-thia-12-azatricyclo[6.3.1.02,7]dodeca-2,4,6-triene
• CAS: 141663-74-3
• 化学式: C₂₁H₂₅NS
• 分子量: 323.502
• InChiKey: HPJYLGYGBMVCGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯基)-1-异吲哚啉酮 在 劳森试剂 作用下， 以 甲苯 、 苯 为溶剂， 生成 10,10,11,11-Tetramethyl-12-(4-methylphenyl)-9-thia-12-azatricyclo[6.3.1.02,7]dodeca-2,4,6-triene
  参考文献：
  名称：

  Photoreactions of isoindoline-1-thiones with alkenes: unusual formation of tricyclic isoindolines

  摘要：

  Photochemical cycloaddition reactions of cyclic thioamides and alkenes have been examined. Irradiation of 2-arylisoindoline-1-thiones 1 in the presence of alkenes 2 gave the unexpected tricyclic isoindolines 3-18. The formation of tricyclic isoindolines can best be explained in terms of the intermediacy of aminospirothietane 27, formed by [2 + 2] photocycloaddition of the C=S double bond of 1 to the C=C double bond of 2. Ring cleavage of the resultant amino thietane, assisted by the participation of the nitrogen lone-pair electrons, produced zwitterions 28 and 29 or 1-mercaptoethylisoindole (30). Subsequent nucleophilic attack of the thiol anion on the iminium carbon of 29 or attack of the thiol group on C-3 of 30 gave the final products. Irradiation of isobenzofuran-1-thione (22) and isobenzothiophene-l-thione (23) in the presence of tetramethylethylene (2a) gave the corresponding spirothietanes 24 and 25.

  DOI：

  10.1021/jo00040a049