2-phenylthiocarbamoyl-2,6-dimethylpiperazin-3-one | 511310-38-6

• 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-2,6-dimethylpiperazin-3-one
• 英文别名: 2,6-dimethyl-3-oxo-N-phenylpiperazine-2-carbothioamide
• CAS: 511310-38-6
• 化学式: C₁₃H₁₇N₃OS
• 分子量: 263.363
• InChiKey: GCSYFNWWAFSWDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  二碘甲烷 、 2-phenylthiocarbamoyl-2,6-dimethylpiperazin-3-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以56%的产率得到2-phenyl-3a,7-dimethyl-3-thioxoimidazolidin[1,5-a]piperazin-4-one
  参考文献：
  名称：

  饱和咪唑烷[1,5-a]-和噻唑烷[3,4-a]perhydroquinoxalin-4-one和咪唑烷[1,5-a]哌嗪-4-one衍生物的合成。Perhydroquinoxalin-4-one 成 Perhydrobenzimidazolin-2-one 的环收缩

  摘要：

  通过缩合反应制备饱和稠合体系，如咪唑啉[1,5-a]-和噻唑烷[3,4-a]全氢喹喔啉-4-酮以及咪唑啉[1,5-a]哌嗪-4-酮衍生物适当的 perhydroquinoxalin-3-one 和 piperazin-3-one 衍生物与二碘甲烷和硫光气。使用同步加速器和实验室辐射源的晶体结构分析证明，通过与 1,2-二溴乙烷反应，perhydroquinoxalin-3-one 衍生物与 perhydrobenzimidazolidin-2-one 衍生物发生不寻常的环收缩。

  DOI：

  10.1055/s-2004-829185
• 作为产物：
  描述：

  1,2-丙二胺 、 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide 以 乙醇 为溶剂， 反应 0.08h， 以51%的产率得到2-phenylthiocarbamoyl-2,6-dimethylpiperazin-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

• Zaleska, Barbara; Karelus, Marcin; Serda, Pawel, Journal of Chemical Research, 2007, # 1, p. 22 - 23
  作者：Zaleska, Barbara、Karelus, Marcin、Serda, Pawel

  DOI：——

  日期：——
• 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%.
• Synthesis of Saturated Imidazolidin[1,5-<i>a</i>]- and Thiazolidin[3,4-<i>a</i>]perhydroquinoxalin-4-one and Imidazolidin[1,5-<i>a</i>]piperazin-4-one Derivatives. Ring Contraction of Perhydroquinoxalin-4-one to Perhydrobenzimidazolin-2-one
  作者：Barbara Zaleska、Robert Socha、Marcin Karelus、Jacek Grochowski、Paweł Serda

  DOI：10.1055/s-2004-829185

  日期：——

  Saturated fused systems such as imidazolidin[ 1,5-a]- and thiazolidin[3,4-a]perhydroquinoxalin-4-one as well as imidazolidin[1,5-a]piperazin-4-one derivatives were prepared by cyclocondensation reactions of appropriate perhydroquinoxalin-3-one and piperazin-3-one derivatives with diiodomethane and thiophosgene. An unusual ring contraction of perhydroquinoxalin-3-one derivatives to perhydrobenzimidazolidin-2-one

  通过缩合反应制备饱和稠合体系，如咪唑啉[1,5-a]-和噻唑烷[3,4-a]全氢喹喔啉-4-酮以及咪唑啉[1,5-a]哌嗪-4-酮衍生物适当的 perhydroquinoxalin-3-one 和 piperazin-3-one 衍生物与二碘甲烷和硫光气。使用同步加速器和实验室辐射源的晶体结构分析证明，通过与 1,2-二溴乙烷反应，perhydroquinoxalin-3-one 衍生物与 perhydrobenzimidazolidin-2-one 衍生物发生不寻常的环收缩。