2-Methyl-5-phenylthio-2H-isoindol-4,7-dion | 139592-95-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-Methyl-5-phenylthio-2H-isoindol-4,7-dion
• 英文别名: 2-methyl-5-phenylthio-2H-isoindole-4,7-dione；2-methyl-5-phenylsulfanylisoindole-4,7-dione
• CAS: 139592-95-3
• 化学式: C₁₅H₁₁NO₂S
• 分子量: 269.324
• InChiKey: JOJNJZRTBSUHRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  64.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  肌氨酸 、 2-(苯硫基)-P-苯醌 在 聚合甲醛 作用下， 反应 0.75h， 以60%的产率得到2-Methyl-5-phenylthio-2H-isoindol-4,7-dion
  参考文献：
  名称：

  Synthese und polarographisches Verhalten von 2H-Isoindol-4,7-dionen

  摘要：

  2-Phenylthio-1,4-benzoquinone (1 a) reacts with azomethine ylide AY-A to give 2-methyl-5-phenylthio-2H-isoindole-4,7-dione (4 f). With 2-(N-methylanilino)-5-methyl-1,4-benzoquinone (1 b), the azomethine ylide AY-B undergoes cycloaddition to yield an inseparable mixture of 5a-methyl-8-(N-methylanilino)-2,3,5,5a,9a,9b-hexahydro-pyrrolo[2,1-a]1H-isoindole-6,9-dione (5 bI) and 9a-methyl-7-(N-methylanilino)-2,3,5,5a,9a,9b-hexahydropyrrolo[2,1-a]1H-isoindole-6,9-dione (5 bII). The structures of 5 bI and 5 bII were established on basis of two-dimensional-NMR-techniques. The mechanism of the cycloaddition of azomethine ylides to 1,4-quinones was studied on basis of cyclovoltammetric investigations. To determine the electron affinity of the isoindoledione derivatives 4 a-f and 5 a-b the peak potentials were measured by differential pulse polarography (DPP).

  DOI：

  10.1007/bf00823429