4-methyl-3-phenacylthio-3-cyanopyridin-6-one | 93272-86-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methyl-3-phenacylthio-3-cyanopyridin-6-one
• 英文别名: 4-methyl-6-oxo-2-phenacylsulfanyl-1H-pyridine-3-carbonitrile
• CAS: 93272-86-7
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: GQWVQZNEVACPKC-UHFFFAOYSA-N

物化性质

• 熔点：
  211-212 °C(Solv: N,N-dimethylformamide (68-12-2))
• 沸点：
  481.7±45.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  95.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-3-phenacylthio-3-cyanopyridin-6-one 在 氢氧化钾 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-amino-4-benzoyl-4-methyl-6-oxo-7H-thieno<2,3-b>pyridine
  参考文献：
  名称：

  Dyachenko, V. D.; Sharanin, Yu. A.; Shestopalov, A. M., Journal of general chemistry of the USSR, 1990, vol. 60, # 10, p. 2131 - 2138

  摘要：

  DOI：
• 作为产物：
  描述：

  morpholinium 3-cyano-4-methyl-6-oxo-1,6-dihydropyridine-2-thiolate 、 2-溴苯乙酮 以 苯 为溶剂， 反应 6.0h， 以89%的产率得到4-methyl-3-phenacylthio-3-cyanopyridin-6-one
  参考文献：
  名称：

  New method of synthesis of substituted 2-pyridones

  摘要：

  DOI：

  10.1007/bf00959212

文献信息

• Microwave Assisted Synthesis and Unusual Coupling of Some Novel Pyrido[3,2-f][1,4]thiazepines
  作者：Rasha M. Faty、Mohamed M. Youssef、Ayman M.S. Youssef

  DOI：10.3390/molecules16064549

  日期：——

  3-Amino-3-thioxopropanamide (1) reacted with ethyl acetoacetate to form 6-hydroxy-4-methyl-2-thioxo-2,3-dihydropyridine-3-carboxamide (2), which reacted with α-haloketones 3 to produce 2,3-disubstituted-8-hydroxy-6-methyl-2H,5H-pyrido[3,2-f]-[1,4]thiazepin-5-ones 4a-c. Benzoylation of 4c led to the formation of the dibenzoate derivative 9. Compounds 4a-c could be prepared stepwise through the formation of S-alkylated derivatives 10a-c. Compounds 2, 4a-c, 9 and 10a-c were prepared using microwave as a source of heat, and gave better yields in shorter times than those achieved by traditional methods. Coupling of 4a-c with arenediazonium chlorides proceeded unusually to give the 6-hydroxy-4-methyl-2-(arylazo)thieno[2,3-b]pyridin-3(2H)-one ring contraction products 14. Structures of the newly synthesized compounds were proven by spectral and chemical methods.

  3-氨基-3-硫代丙酰胺（1）与乙酰乙酸乙酯反应，生成6-羟基-4-甲基-2-硫代-2,3-二氢吡啶-3-羧酰胺（2），该化合物又与α-卤酮3反应，产生2,3-二取代-8-羟基-6-甲基-2H,5H-吡啶[3,2-f]-[1,4]噻嗪-5-酮类化合物4a-c。4c的苯甲酰化反应生成二苯甲酸酯衍生物9。化合物4a-c可以通过S-烷基化衍生物10a-c的逐步合成制备。化合物2、4a-c、9和10a-c均采用微波加热的方法制备，与传统方法相比，产率更高、时间更短。化合物4a-c与芳基重氮盐氯化物的偶联反应不寻常地生成了6-羟基-4-甲基-2-(芳基偶氮)噻吩[2,3-b]吡啶-3(2H)-酮的环缩合产物14。新合成化合物的结构通过光谱和化学方法得到了验证。
• Synthesis of Substituted 1,3-Cyclohexadienes, Pyridine-2(1H)-thiones, and Thieno[2,3-d]pyrimidine- 4(3H)-thiones by the Michael Reaction
  作者：V. D. Dyachenko、A. D. Dyachenko、A. N. Chernega

  DOI：10.1023/b:rujo.0000034978.81993.bd

  日期：2004.3

  Cyclopentylidene- and cyclohexylidene(cyano)acetamides reacted with malononitrile and cyano-(thioacetamide) according to the Michael pattern with exchange of the methylene components to give substituted 1-amino-2,6,6-tricyano-1,3-cyclohexadienes and thieno[2,3-d]pyrimidine-4(3H)-thiones. Condensation of cyclopentylidene- and cyclohexylidene(cyano)acetamide with 1,3-dicarbonyl compounds afforded 4,6-dimethyl-3-cyanopyridine-2(1H)-thione and morpholinium 4-methyl-6-oxo-3-cyano-1,6-dihydropyridine-2-thiolate which were converted into substituted 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridine, and 2H-[1,3]thiazino[3,2-a]pyridine.
• New method of synthesis of substituted 2-pyridones
  作者：V. P. Litvinov、Yu. A. Sharanin、B. K. Promonenkov、L. A. Rodinovskaya、A. M. Shestopalov、V. Yu. Mortikov

  DOI：10.1007/bf00959212

  日期：1984.8
• DYACHENKO, V. D.;SHARANIN, YU. A.;SHESTOPALOV, A. M.;RODINOVSKAYA, L. A.;+, ZH. OBSHCH. XIMII, 60,(1990) N0, S. 2384-2392
  作者：DYACHENKO, V. D.、SHARANIN, YU. A.、SHESTOPALOV, A. M.、RODINOVSKAYA, L. A.、+

  DOI：——

  日期：——
• LITVINOV, V. P.;SHARANIN, YU. A.;PROMONENKOV, V. K.;RODINOVSKAYA, L. A.;S+, IZV. AN CCCP. CEP. XIM., 1984, N 8, 1869-1870
  作者：LITVINOV, V. P.、SHARANIN, YU. A.、PROMONENKOV, V. K.、RODINOVSKAYA, L. A.、S+

  DOI：——

  日期：——