2-carbamothioyl-N-(3-methylphenyl)acetamide | 501037-55-4

• 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-carbamothioyl-N-(3-methylphenyl)acetamide
• 英文别名: 3-amino-N-(3-methylphenyl)-3-sulfanylidenepropanamide
• CAS: 501037-55-4
• 化学式: C₁₀H₁₂N₂OS
• mdl: MFCD05266702
• 分子量: 208.284
• InChiKey: PSCQQPZLJBHYGH-UHFFFAOYSA-N

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：

  2-carbamothioyl-N-(3-methylphenyl)acetamide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 4.08h， 生成 diethyl 2-{[1-pentylsulfanyl-2-(m-tolylaminocarbonyl)ethenylamino]methylidene}malonate
  参考文献：
  名称：

  Competing processes in the condensation of diethyl ethoxymethylidenemalonate and malononitrile derivatives with CH acids containing a thiocarbamoyl group

  摘要：

  Diethyl ethoxymethylidenemalonate and ethoxymethylidenemalononitrile react with CH acids containing a thiocarbamoyl group along several concurrent pathways to give both acyclic structures and pyridine and pyrimidine derivatives.

  DOI：

  10.1134/s1070363207010161
• 作为产物：
  描述：

  2-氰基-N-间甲苯乙酰胺 在 硫化氢 、 三乙胺 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以86%的产率得到2-carbamothioyl-N-(3-methylphenyl)acetamide
  参考文献：
  名称：

  摘要：

  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.

  DOI：

  10.1023/a:1020912932335

文献信息

• 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.
• 4-Alkyl-6-amino-N 3,N 5-diaryl-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides: II. Synthesis and selected reactions
  作者：V. D. Dyachenko、E. N. Karpov、I. A. Feskov

  DOI：10.1134/s1070363213090156

  日期：2013.9

  New 4-alkyl-6-amino-N (3),N (5)-diaryl-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides have been prepared via enantioselective reaction of 3-amino-N-aryl-3-thioxopropanamides with N-aryl-2-cyanoacetamide and aliphatic aldehydes. The prepared products can be regioselectively alkylated at sulfur atom.
• Synthesis and alkylation of n(3)-aryl-n(5)-phenyl-6-amino-4-aryl(2-furyl)-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamide
  作者：V. D. Dyachenko、D. A. Krasnikov、M. V. Khorik

  DOI：10.1007/s10593-008-0114-5

  日期：2008.7

  N-(3)-Aryl-N-(5)-phenyl-6-amino-4-aryl(2-furyl)-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides have been obtained by the interaction of N-phenyl-3-aryl(2-furyl)-2-cyanoacrylamides with 3-amino-3-thioxopropananilides under the conditions of the Michael reaction. N-(3)-Aryl-N-(5)-phenyl-2-alkylthio-6-amino-4-aryl(2-furyl)-3,4-dihydropyridine-3,5-dicarboxamides and N-(3), N-(5)-diphenyl-6-benzylthio-4-(2-furyl)-2-oxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides were synthesized by alkylation of the products.
• 4-alkyl-6-amino-4-N 3,N 5-diaryl-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides: I. Tandem synthesis and alkylation. Molecular and crystal structure of 6-allylsulfanyl-2-amino-4-isobutyl-N 3,N 5-di-m-tolyl-3,4-dihydropyridine-3,5-dicarboxamide
  作者：V. D. Dyachenko、E. N. Karpov

  DOI：10.1134/s1070363213070153

  日期：2013.7

  4-Alkyl-6-amino-4-N (3),N (5)-diaryl-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides were obtained via tandem synthesis involving the Knoevenagel reaction, Michael reaction and intramolecular condensation. Alkylation of the obtained dicarboxamides proceeds regioselectively at the S atom to form the corresponding thioethers. Structure of 6-allylsulfanyl-2-amino-4-isobutyl-N (3),N (5)-di-m-tolyl-3,4-dihydropyridine-3,5-dicarboxamide was uniquely determined by XRD analysis.
• Synthesis of new functionally substituted 2-oxo(thioxo)nicotinic acid amides and nitriles by SNVin reaction
  作者：V. D. Dyachenko、O. S. Bityukova、A. D. Dyachenko

  DOI：10.1134/s1070428011090132

  日期：2011.9

  New functionally substituted 2-oxo- and 2-thioxonicotinic acid amides and nitriles were synthesized by condensation of 3,3-bis(methylsulfanyl)acrylonitriles with CH acids according to the S(N)Vin pattern.