3-oxo-N-p-tolyl-thiobutyramide | 60728-85-0

• 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-p-tolyl-thiobutyramide
• 英文别名: 1-thio-acetoacetic acid p-toluidide；1-Thio-acetessigsaeure-p-toluidid；Acetylthioessigsaeure-p-toluidid；Butanethioamide, N-(4-methylphenyl)-3-oxo-；N-(4-methylphenyl)-3-oxobutanethioamide
• CAS: 60728-85-0
• 化学式: C₁₁H₁₃NOS
• 分子量: 207.296
• InChiKey: WXUXSVNLIJMYRD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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-p-tolyl-thiobutyramide 以 苯 为溶剂， 反应 0.02h， 生成 (+/-)-2-methyl-3-(4-methylphenylthiocarbamoyl)-trans-4a,5,6,7,8,8a-hexahydroquinoxaline
  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：

  2-acetyl-3-oxo-thiobutyric acid p-toluidide 在 氢氧化钾 作用下， 生成 3-oxo-N-p-tolyl-thiobutyramide
  参考文献：
  名称：

  Worrall, Journal of the American Chemical Society, 1920, vol. 42, p. 1058

  摘要：

  DOI：

文献信息

• Synthesis of 3-(6-R-Benzothiazol-2-yl)-4-methyl-1,2,5-oxadiazoles
  作者：V. N. Britsun、A. N. Borisevich、L. S. Samoilenko、M. O. Lozinskii

  DOI：10.1007/s11178-005-0237-4

  日期：2005.5

  The nitrosation of N-aryl-3-oxobutanethioamides afforded 1-(6-R-benzothiasol-2-yl)-1-hydroxyimino-2-propanones that at oximation with hydroxylamine were converted into 1-(6-R-benzothiazol-2-yl)-1,2-dihydroxyiminopropanes. The latter were dehydrated by heating with succinic anhydride at 140°C yielding therewith 3-(6-R-benzothiazol-2-yl)-4-methyl-1,2,5-oxadiazoles.

  通过对 N-芳基-3-氧代丁硫酰胺进行亚硝基化反应，可得到 1-(6-R-苯并噻唑-2-基)-1-羟基亚氨基-2-丙酮，在与羟胺进行氧化反应后，可转化为 1-(6-R-苯并噻唑-2-基)-1,2-二羟基亚氨基丙烷。后者在 140°C 下用丁二酸酐加热脱水，得到 3-(6-R-苯并噻唑-2-基)-4-甲基-1,2,5-恶二唑。
• 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.
• 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).
• Reaction of arylamides of acetylthioacetic acid with maleic anhydride
  作者：A. N. Borisevich、P. S. Pel'kis

  DOI：10.1007/bf00475736

  日期：1971.7