2-anilino-N-(4-chlorophenyl)-2-ethoxy-3-oxobutanethioamide | 324000-19-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-anilino-N-(4-chlorophenyl)-2-ethoxy-3-oxobutanethioamide
• CAS: 324000-19-3
• 化学式: C₁₈H₁₉ClN₂O₂S
• 分子量: 362.88
• InChiKey: FJGLGCJMNNHXRH-UHFFFAOYSA-N

物化性质

• 沸点：
  536.6±60.0 °C(Predicted)
• 密度：
  1.315±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  50.36
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-anilino-N-(4-chlorophenyl)-2-ethoxy-3-oxobutanethioamide 、 trans-1,2-Diaminocyclohexane 以 乙醇 为溶剂， 反应 0.08h， 以54%的产率得到(+/-)-2-acetyl-2-(4-chlorophenylthiocarbamoyl)-(3a,7a)-trans-perhydrobenzimidazole
  参考文献：
  名称：

  Synthesis of Enantiopure Chiral Perhydrobenzimidazole and Hexahydroquinoxaline Derivatives

  摘要：

  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.

  DOI：

  10.1007/s007060070038
• 作为产物：
  描述：

  Acetthioessigsaeure-(4-chloranilid) 在 sodium hydroxide 作用下， 以 叔丁醇 为溶剂， 反应 0.5h， 生成 2-anilino-N-(4-chlorophenyl)-2-ethoxy-3-oxobutanethioamide
  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 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%.