2-(benzylthio)-4-morpholino-4-thioxobutanenitrile | 1450914-14-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 2-(benzylthio)-4-morpholino-4-thioxobutanenitrile
• 英文别名: 2-Benzylsulfanyl-4-morpholin-4-yl-4-sulfanylidenebutanenitrile
• CAS: 1450914-14-3
• 化学式: C₁₅H₁₈N₂OS₂
• 分子量: 306.453
• InChiKey: PWQMOZMAPSYVFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-(4-吗啉基)-2-硝基噻吩 、 苄硫醇 在 溶剂黄146 、 锌 作用下， 以 甲苯 为溶剂， 反应 1.17h， 以5%的产率得到2-(benzylthio)-4-morpholino-4-thioxobutanenitrile
  参考文献：
  名称：

  A Remarkable Reductive Dearomatization of Thiophene and Furan Rings

  摘要：

  Reduction of a 2-nitrothiophene 4 and the corresponding 2-nitrofuran 20 with zinc and acetic acid produced a remarkable dearomatization and fragmentation reaction to give acyclic nitriles 6 and 22, respectively. The intermediate 2-aminothiophene 5 was trapped by acylation with acetic anhydride to give acetamide 7. An additional acrylonitrile intermediate 17 was also trapped by Michael addition with benzyl mercaptan to give adduct 18. An alternate synthesis of nitrile 22 produced in the reduction of nitrofuran 20 provided an authentic sample of the product. The conversion of nitroaromatic heterocycles 4 and 20 into aliphatic nitriles 6 and 22 are remarkable and unprecedented reactions.

  DOI：

  10.1055/s-0033-1338416