(+/-)-2-phenylthiocarbamoyl-2-methyl-trans-perhydroquinoxalin-3-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+/-)-2-phenylthiocarbamoyl-2-methyl-trans-perhydroquinoxalin-3-one
• 英文别名: (2S,4aS,8aS)-2-methyl-3-oxo-N-phenyl-1,4,4a,5,6,7,8,8a-octahydroquinoxaline-2-carbothioamide
• 化学式: C₁₆H₂₁N₃OS
• 分子量: 303.428
• InChiKey: XAZUNPNJSKCPMY-XEZPLFJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  trans-1,2-dibromocyclohexane 、 (+/-)-2-phenylthiocarbamoyl-2-methyl-trans-perhydroquinoxalin-3-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 以20%的产率得到
  参考文献：
  名称：

  Synthesis of 1,4-Diazines by Ring Expansion of 1,3-Diazines

  摘要：

  Fully saturated piperazin-3-one and quinoxalin-3-one derivatives were prepared by reactions of 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide with aliphatic 1,2-diamines. An unusual ring expansion of the intermediate 1,3-diazines leads to 1,4-diazines. Moreover, quinoxalin-3-one derivatives from chiral trans-1,2-diaminocyclohexane were obtained with diastereoselectivity >95%.

  DOI：

  10.1021/jo026756t
• 作为产物：
  描述：

  (1S,2S)-(+)-1,2-环己二胺 、 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide 以 乙醇 为溶剂， 反应 0.08h， 以78%的产率得到(+/-)-2-phenylthiocarbamoyl-2-methyl-trans-perhydroquinoxalin-3-one
  参考文献：
  名称：

  Synthesis of 1,4-Diazines by Ring Expansion of 1,3-Diazines

  摘要：

  Fully saturated piperazin-3-one and quinoxalin-3-one derivatives were prepared by reactions of 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide with aliphatic 1,2-diamines. An unusual ring expansion of the intermediate 1,3-diazines leads to 1,4-diazines. Moreover, quinoxalin-3-one derivatives from chiral trans-1,2-diaminocyclohexane were obtained with diastereoselectivity >95%.

  DOI：

  10.1021/jo026756t

文献信息

• Synthesis of 1,4-Diazines by Ring Expansion of 1,3-Diazines
  作者：Barbara Zaleska、Robert Socha、Marcin Karelus、Edward Szneler、Jacek Grochowski、Paweł Serda

  DOI：10.1021/jo026756t

  日期：2003.3.1

  Fully saturated piperazin-3-one and quinoxalin-3-one derivatives were prepared by reactions of 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide with aliphatic 1,2-diamines. An unusual ring expansion of the intermediate 1,3-diazines leads to 1,4-diazines. Moreover, quinoxalin-3-one derivatives from chiral trans-1,2-diaminocyclohexane were obtained with diastereoselectivity >95%.