2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide | 324000-16-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide
• 英文别名: 2-anilino-2-ethoxy-3-oxothiobutyric acid anilide；2-anilino-2-ethoxy-3-oxo-N-phenylbutanethioamide
• CAS: 324000-16-0
• 化学式: C₁₈H₂₀N₂O₂S
• 分子量: 328.435
• InChiKey: PVKKWNMJGHUVES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide 在 肼 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以47%的产率得到4-anilino-5-phenylimino-3-methylpyrazoline
  参考文献：
  名称：

  两性离子化合物的合成：通过3-氧代丁酸硫代苯胺衍生物的新型重排，完全饱和的嘧啶鎓和1,3-二氮杂吡啶鎓衍生物。

  摘要：

  在2-苯胺基-2-乙氧基-3-氧代硫代丁酸与脂族1，3-以及1，4-二胺环化后，发生异常的重排，导致2-羟基丙酸的两性离子衍生物。而且，通过芳族1,2-二胺，获得了稠合的杂环系统，例如蝶啶，喹喔啉和吡啶并[2,3-b]吡嗪。

  DOI：

  10.1021/jo025602a
• 作为产物：
  描述：

  丁硫代酰胺,3-羰基-N-苯基- 在 sodium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 0.5h， 生成 2-anilino-2-ethoxy-3-oxothiobutanoic acid anilide
  参考文献：
  名称：

  Spectroscopic Study of the Conformation of 2-Anilino-2-ethoxy-3-oxothiobutyric Acid Anilides

  摘要：

  An NMR study of the equilibrium mixture of two conformers of 2-anilino-2-ethoxy-3-oxothiobutyric acid anilides 3 allows to estimate their population ratio in solvents of increasing polarity. X-Ray analysis as well as IR spectroscopy confirmed that the conformer present in the solid state is stabilized by two hydrogen bonds. The structural basis of the second conformer observed in solution is the 1,4-type S...O interaction between the sulfur of the thioanilide moiety and the oxygen of the ethoxy group with a distance of 2.878 Angstrom.

  DOI：

  10.1007/s007060070022

文献信息

• Synthesis of Enantiopure Chiral Perhydrobenzimidazole and Hexahydroquinoxaline Derivatives
  作者：Barbara Zaleska、Robert Socha

  DOI：10.1007/s007060070038

  日期：2000.10.16

  Starting from 2-anilino-2-ethoxy-3-oxothiobutyric acid anilides and (R,R)-or (S,S)-trans-1,2-diaminocyclohexane, chiral C2-disubstituted perhydrobenzimidazole and trans-4a,5,6,7,8,8a-hexahydroquinoxaline derivatives were obtained depending on the polarity of the solvent.
• 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 Zwitterionic Compounds:  Fully Saturated Pyrimidinylium and 1,3-Diazepinylium Derivatives via the Novel Rearrangement of 3-Oxobutanoic Acid Thioanilide Derivatives
  作者：Barbara Zaleska、Tomasz Bazanek、Robert Socha、Marcin Karelus、Jacek Grochowski、Paweł Serda

  DOI：10.1021/jo025602a

  日期：2002.6.1

  An unusual rearrangement following cyclization of 2-anilino-2-ethoxy-3-oxothiobutanoic acid with aliphatic 1,3- as well as 1,4-diamine leads to zwitterionic derivatives of 2-hydroxypropanoic acid. Moreover, with aromatic 1,2-diamines, fused heterocyclic systems such as pteridine, quinoxaline, and pyrido[2,3-b]pyrazine are obtained.

  在2-苯胺基-2-乙氧基-3-氧代硫代丁酸与脂族1，3-以及1，4-二胺环化后，发生异常的重排，导致2-羟基丙酸的两性离子衍生物。而且，通过芳族1,2-二胺，获得了稠合的杂环系统，例如蝶啶，喹喔啉和吡啶并[2,3-b]吡嗪。
• Spectroscopic Study of the Conformation of 2-Anilino-2-ethoxy-3-oxothiobutyric Acid Anilides
  作者：Barbara Zaleska、Robert Socha、Maria Ciechanowicz-Rutkowska、Tulio Pilati

  DOI：10.1007/s007060070022

  日期：2000.11.13

  An NMR study of the equilibrium mixture of two conformers of 2-anilino-2-ethoxy-3-oxothiobutyric acid anilides 3 allows to estimate their population ratio in solvents of increasing polarity. X-Ray analysis as well as IR spectroscopy confirmed that the conformer present in the solid state is stabilized by two hydrogen bonds. The structural basis of the second conformer observed in solution is the 1,4-type S...O interaction between the sulfur of the thioanilide moiety and the oxygen of the ethoxy group with a distance of 2.878 Angstrom.