14,14-dimethyl-7-methylsulfanyl-3-phenyl-2,13,15-trioxa-8-azatricyclo[9.4.0.04,8]pentadeca-1(11),4,6-trien-12-one | 225502-94-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 14,14-dimethyl-7-methylsulfanyl-3-phenyl-2,13,15-trioxa-8-azatricyclo[9.4.0.04,8]pentadeca-1(11),4,6-trien-12-one
• CAS: 225502-94-3
• 化学式: C₂₀H₂₁NO₄S
• 分子量: 371.457
• InChiKey: VPAXNGIBGFIJJV-UHFFFAOYSA-N

物化性质

• 沸点：
  556.5±50.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.69
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  14,14-dimethyl-7-methylsulfanyl-3-phenyl-2,13,15-trioxa-8-azatricyclo[9.4.0.04,8]pentadeca-1(11),4,6-trien-12-one 在 PPA 作用下， 反应 17.0h， 以17.6%的产率得到3-Methylsulfanyl-9-phenyl-5,6-dihydro-4H,9H-8-oxa-3a-aza-cyclopentacycloocten-7-one
  参考文献：
  名称：

  An Anomalous Preparing of a Tetrahydro-2H-oxocine Fused Pyrrole Derivative and Its Acid-catalyzed Rearrangement

  摘要：

  Condensation of 5-methylthio-2-benzoylpyrrole (1) with spiro[2.5]-5,7-dioxa-6,6-dimethyloctane-4,8-dione (3) using excess amount of NaH in DMF gave an anomalous tetrahydro-2H-oxocine fused pyrrole (10), which then undergoes an acid-catalyzed rearrangement in refluxing toluene/methanol (10:1, V/V) to afford the unexpected anti-aromatic compounds (15 and 16).

  DOI：

  10.3987/com-98-8437
• 作为产物：
  描述：

  5-[2-(2-Benzoyl-5-methylsulfanyl-pyrrol-1-yl)-ethyl]-2,2-dimethyl-[1,3]dioxane-4,6-dione 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以46.4%的产率得到14,14-dimethyl-7-methylsulfanyl-3-phenyl-2,13,15-trioxa-8-azatricyclo[9.4.0.04,8]pentadeca-1(11),4,6-trien-12-one
  参考文献：
  名称：

  An Anomalous Preparing of a Tetrahydro-2H-oxocine Fused Pyrrole Derivative and Its Acid-catalyzed Rearrangement

  摘要：

  Condensation of 5-methylthio-2-benzoylpyrrole (1) with spiro[2.5]-5,7-dioxa-6,6-dimethyloctane-4,8-dione (3) using excess amount of NaH in DMF gave an anomalous tetrahydro-2H-oxocine fused pyrrole (10), which then undergoes an acid-catalyzed rearrangement in refluxing toluene/methanol (10:1, V/V) to afford the unexpected anti-aromatic compounds (15 and 16).

  DOI：

  10.3987/com-98-8437

文献信息

• An Anomalous Preparing of a Tetrahydro-2H-oxocine Fused Pyrrole Derivative and Its Acid-catalyzed Rearrangement
  作者：Shan-Yen Chou、Lien-Shange Chang、Shyh-Fong Chen

  DOI：10.3987/com-98-8437

  日期：——

  Condensation of 5-methylthio-2-benzoylpyrrole (1) with spiro[2.5]-5,7-dioxa-6,6-dimethyloctane-4,8-dione (3) using excess amount of NaH in DMF gave an anomalous tetrahydro-2H-oxocine fused pyrrole (10), which then undergoes an acid-catalyzed rearrangement in refluxing toluene/methanol (10:1, V/V) to afford the unexpected anti-aromatic compounds (15 and 16).