3-amino-N-(4-methylphenyl)-3-thioxopropanamide | 369609-88-1

• 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: 3-amino-N-(4-methylphenyl)-3-thioxopropanamide
• 英文别名: 3-amino-N-(4-methylphenyl)-3-sulfanylidenepropanamide
• CAS: 369609-88-1
• 化学式: C₁₀H₁₂N₂OS
• mdl: MFCD00778304
• 分子量: 208.284
• InChiKey: SXXPRNOXALFYGL-UHFFFAOYSA-N

物化性质

• 密度：
  1.270±0.06 g/cm3(Predicted)
• 溶解度：
  30.7 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  87.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-amino-N-(4-methylphenyl)-3-thioxopropanamide 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 129.0h， 生成 ethyl [(2-{2-[(4-methylphenyl)amino]-2-oxoethyl}-5-[N-(4-methylphenyl)carbamoyl]pyrimidin-4-yl)thio]acetate
  参考文献：
  名称：

  3-氨基-3-硫代丙酰胺与1，3-二羰基化合物的2-苯胺基亚甲基衍生物反应的出乎意料的结果。嘧啶-5-羧酰胺衍生物的合成

  摘要：

  3-氨基-3-硫代丙酰胺与二甲酮，1,3-环己二酮和Meldrum酸的2-苯胺基亚甲基衍生物的相互作用导致形成2-（2-氨基-2-氧代乙基）-6-硫代氧杂1,6 -二氢嘧啶-5-羧酰胺。将后者在碱性介质中烷基化，形成4-（烷硫基）嘧啶-5-羧酰胺衍生物。

  DOI：

  10.1007/s10593-013-1266-5
• 作为产物：
  描述：

  2-氰基对甲苯乙酰胺 在 吡啶 、 硫化氢 、 三乙胺 作用下， 生成 3-amino-N-(4-methylphenyl)-3-thioxopropanamide
  参考文献：
  名称：

  The Mannich reaction in the synthesis of N,S-containing heterocycles 12. First example of aminomethylation involving 2-thioxonicotinamide derivative: synthesis of 3,5,7,11-tetraazatricyclo[7.3.1.02,7]tridec-2-ene-9-carboxamides

  摘要：

  6-amino-5-cyano-3-N-(4-methylphenyl)carbamoyl-4-phenyl-1,4-dihydro-pyridine-2-thiolate 哌啶在伯胺和过量甲醛的作用下发生氨基甲基化反应，生成 3,5,7,11-四氮杂三环[7.3.1.02,7]十三-2-烯-9-甲酰胺，产率为 36-52%。

  DOI：

  10.1007/s11172-012-0019-4

文献信息

• The Mannich reaction in the synthesis of N,S-containing heterocycles 12. First example of aminomethylation involving 2-thioxonicotinamide derivative: synthesis of 3,5,7,11-tetraazatricyclo[7.3.1.02,7]tridec-2-ene-9-carboxamides
  作者：V. V. Dotsenko、S. G. Krivokolysko、V. P. Litvinov

  DOI：10.1007/s11172-012-0019-4

  日期：2012.1

  Piperidinium 6-amino-5-cyano-3-N-(4-methylphenyl)carbamoyl-4-phenyl-1,4-dihydro-pyridine-2-thiolate upon the action of primary amines and excess formaldehyde undergoes aminomethylation to form 3,5,7,11-tetraazatricyclo[7.3.1.02,7]tridec-2-ene-9-carboxamides in 36–52% yields.

  6-amino-5-cyano-3-N-(4-methylphenyl)carbamoyl-4-phenyl-1,4-dihydro-pyridine-2-thiolate 哌啶在伯胺和过量甲醛的作用下发生氨基甲基化反应，生成 3,5,7,11-四氮杂三环[7.3.1.02,7]十三-2-烯-9-甲酰胺，产率为 36-52%。
• Reactions of malonthioamides and malonamidines with methyl acetylpyruvate as a one-step method to prepare 4-thio- and 4-aminopyrrolo[3,4-c]pyridines
  作者：Vera S. Berseneva、Vasiliy A. Bakulev、Wim Dehaen、Suzanne Toppet、Marina Borovkova

  DOI：10.1016/j.tet.2007.03.054

  日期：2007.5

  We report an efficient one-step approach to 4-thio and 4-aminopyrrolo[3,4-c]pyridines based on the selective reaction of malonthioamides and malonamidines with methyl acetylpyruvate. Structural proof is given by HMBC and HMQC spectra. A cascade heterocyclization mechanism is proposed for the reactions studied. (C) 2007 Elsevier Ltd. All rights reserved.
• ——
  作者：Yu. Yu. Morzherin、M. F. Kosterina、V. S. Berseneva、W. Dehaen、V. A. Bakulev

  DOI：10.1023/a:1020912932335

  日期：——

  The equilibrium concentrations of E- and Z-isomers of thiazolidin-4-ones containing exocyclic double bonds in positions 2 and 5 of the cycle were determined in DMSO-d(6). The influence of the nature of the substituents on the equilibrium position was found. Electron-releasing substituents stabilize the E, Z-configuration and electron-withdrawing substituents stabilize the Z,Z-configuration. The association constants of E- and Z-2-ethoxycarbonyl-methylenethiazolidin-4-ones with the sodium cation were determined by H-1 NMR spectroscopy.
• DANKOVA, E. F.;BAKULEV, V. A.;KOLOBOV, M. YU.;SHISHKINA, V. I.;YASMAN, YA+, XIMIYA GETEROTSIKL. SOED.,(1988) N 9, S. 1269-1273
  作者：DANKOVA, E. F.、BAKULEV, V. A.、KOLOBOV, M. YU.、SHISHKINA, V. I.、YASMAN, YA+

  DOI：——

  日期：——
• Unexpected result in the reaction of 3-amino-3-thioxopropanamides with 2-anilinomethylene derivatives of 1,3-dicarbonyl compounds. synthesis of pyrimidine-5-carboxamide derivatives
  作者：V. V. Dotsenko、K. A. Frolov、S. G. Krivokolysko、V. V. Polovinko

  DOI：10.1007/s10593-013-1266-5

  日期：2013.6

  interaction of 3-amino-3-thioxopropanamides with 2-anilinomethylene derivatives of dimedone, 1,3-cyclohexanedione and Meldrum’s acid led to the formation of 2-(2-amino-2-oxoethyl)-6-thioxo-1,6-dihydropyrimidine-5-carboxamides. The latter were alkylated in alkaline medium with the formation of 4-(alkylthio)pyrimidine-5-carboxamide derivatives.

  3-氨基-3-硫代丙酰胺与二甲酮，1,3-环己二酮和Meldrum酸的2-苯胺基亚甲基衍生物的相互作用导致形成2-（2-氨基-2-氧代乙基）-6-硫代氧杂1,6 -二氢嘧啶-5-羧酰胺。将后者在碱性介质中烷基化，形成4-（烷硫基）嘧啶-5-羧酰胺衍生物。