3-oxo-N-(3-chlorophenyl)butanethioamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-oxo-N-(3-chlorophenyl)butanethioamide
• 英文别名: 3-oxo-N-(3'-chlorophenyl)butanethioamide；N-(3-chlorophenyl)-3-oxobutanethioamide
• 化学式: C₁₀H₁₀ClNOS
• 分子量: 227.714
• InChiKey: YDFWOLDLRKHNLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  61.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-oxo-N-(3-chlorophenyl)butanethioamide 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 3-oxo-N-(3-chlorophenyl)butanethioamide sodium salt
  参考文献：
  名称：

  Protolytic properties of 2-acylthioacetamides

  摘要：

  Concentration acidity of 2-acylthioacetamides dissolved in DMSO-H2O was measured by the method of pH-metric titration. The data obtained were extrapolated for the determination of pK (a) values of 2-acylthioacetamides in water and DMSO. We found that in aqueous solutions the acidity of thioacetarylamide (pK (a) = 5.75-6.01) was almost independent of the nature of substituents in their N-phenyl rings, whereas in DMSO solution the nature of substituents significantly affects their ionization constants (pK (a) = 7.88-11.70). The graphs were displayed and the acidity of N-aryl-3-oxobutanethioamides dependence on the Hammett constants of meta- and para-substituents in the phenyl rings derived. Water is shown to be a leveling, and DMSO a differentiating solvent for 2-acylthioacetamides.

  DOI：

  10.1134/s1070363212100106
• 作为产物：
  描述：

  乙酰丙酮 、 3-氯异硫氰酸苯酯 以70%的产率得到
  参考文献：
  名称：

  LUDWIG, E.;UHLEMANN, E., WISS. Z. PAED. HOCHSCH. K. LIEBKNECHT POTSDAM, 1981, 25, N 5, 721-730

  摘要：

  DOI：

文献信息

• Reaction of N-aryl-3-oxobutanethioamides with bis(guanidinium) carbonate
  作者：V. N. Britsun、A. N. Borisevich、M. O. Lozinskii

  DOI：10.1134/s1070428007060188

  日期：2007.6

  Reactions of N-aryl-3-oxobutanethioamides with bis(guanidinium) carbonate lead to the formation of N-aryl-3-guanidinobut-2-enethioamides, 4-arylamino-6-methylpyrimidin-2-amines, guanidinium acetate, and arylamines, depending on the temperature conditions.
• Cyclocondensation of N-aryl-3-oxobutanethioamides with 1H-1,2,4-triazol-5-amine
  作者：V. N. Britsun

  DOI：10.1134/s1070428008100229

  日期：2008.10

  Reactions of N-aryl-3-oxobutanethioamides with 1H-1,2,4-triazole-5-amine give mixtures of 7-arylamino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidines, 5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-7-thione, 7-methyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-5-thione, and 5-arylamino-7-methyl[1,2,4]triazolo[ 1,5-a]pyrimidines whose ratio depends on the substituent in the aryl group of initial N-aryl-3-oxobutanethioamide and solvent nature (the presence of a proton-donor solvent).
• Cyclocondensation of N-aryl-3-oxobutanethioamides with 2-aminoimidazole and 2-aminobenzimidazole
  作者：E. I. Maiboroda、V. N. Britsun

  DOI：10.1134/s1070428008080162

  日期：2008.8

  Cyclization of N-aryl-3-oxobutamthioamides with 2-aminoimidazole and 2-aminobenzimidazole gave 7-methyl-5,8-dilhydroimidazo[1,2-a]pyrimidine-5-thione or 2-methylpyrimido[1,2-a]benzimidazole-4(1H)-thione and 4-(arylamino)-2-methylpyrimido[1,2-a]benzimidazoles whose ratio depends on the nature of aryl substituents in the initial blutamethioamides and on the presence of a prone solvent.
• General trends in reaction of N-aryl-3-oxobutanethioamides with 2-aminoazoles(azines)
  作者：V. N. Britsun、A. N. Borisevich、M. O. Lozinskii

  DOI：10.1134/s1070428007100247

  日期：2007.10

  Reaction products obtained from N-aryl-3-oxobutanethioamides and 2-aminoazoles(azines) are derivatives of (arylamino)pyrimidines and pyrimidinethiones. The ratio of the products depends on the basicity of 1,3-binucleophiles, acidity of the medium, and the character of substituents in the phenyl ring of initial thioamides.
• Protolytic properties of 2-acylthioacetamides
  作者：V. N. Britsun、V. A. Doroshchuk、V. S. Starova、A. B. Ryabitskii、M. O. Lozinskii

  DOI：10.1134/s1070363212100106

  日期：2012.10

  Concentration acidity of 2-acylthioacetamides dissolved in DMSO-H2O was measured by the method of pH-metric titration. The data obtained were extrapolated for the determination of pK (a) values of 2-acylthioacetamides in water and DMSO. We found that in aqueous solutions the acidity of thioacetarylamide (pK (a) = 5.75-6.01) was almost independent of the nature of substituents in their N-phenyl rings, whereas in DMSO solution the nature of substituents significantly affects their ionization constants (pK (a) = 7.88-11.70). The graphs were displayed and the acidity of N-aryl-3-oxobutanethioamides dependence on the Hammett constants of meta- and para-substituents in the phenyl rings derived. Water is shown to be a leveling, and DMSO a differentiating solvent for 2-acylthioacetamides.