5-benzoyl-3-ethoxycarbonyl-1-methyl-6-methylthio-1,2-dihydropyridin-2-one | 1015603-47-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzoyl-3-ethoxycarbonyl-1-methyl-6-methylthio-1,2-dihydropyridin-2-one
• 英文别名: Ethyl 1-methyl-6-(methylsulfanyl)-2-oxo-5-(phenylcarbonyl)-1,2-dihydropyridine-3-carboxylate；ethyl 5-benzoyl-1-methyl-6-methylsulfanyl-2-oxopyridine-3-carboxylate
• CAS: 1015603-47-0
• 化学式: C₁₇H₁₇NO₄S
• 分子量: 331.392
• InChiKey: ZTUJRKVQSCDXBG-UHFFFAOYSA-N

物化性质

• 熔点：
  130-132 °C(Solv: isopropanol (67-63-0))
• 沸点：
  444.4±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  89
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-benzoyl-3-ethoxycarbonyl-1-methyl-6-methylthio-1,2-dihydropyridin-2-one 在 氢氧化钾 、 盐酸羟胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以75%的产率得到5-ethoxycarbonyl-7-methyl-3-phenyl-6,7-dihydroisoxazolo[3,4-b]pyridin-6-one
  参考文献：
  名称：

  Synthesis and reactions of 1-R-3-benzoyl-5-ethoxycarbonyl-6-oxo-1,2,3,6-tetrahydropyridine-2-thiones

  摘要：

  DOI：

  10.1007/s10593-007-0218-3
• 作为产物：
  描述：

  3-benzoyl-5-ethoxycarbonyl-1-methyl-6-oxo-1,2,3,6-tetrahydropyridine-2-thione 、 碘甲烷 以 乙醇 为溶剂， 反应 2.0h， 以12.08 g的产率得到5-benzoyl-3-ethoxycarbonyl-1-methyl-6-methylthio-1,2-dihydropyridin-2-one
  参考文献：
  名称：

  Cyclocondensation of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyrid-2-ones with heterocyclic N,N-and N,C-1,3-dinucleophiles

  摘要：

  [3+3] Cyclocondensation of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyrid-2-ones with heterocyclic N,N- and N,C-1,3-dinucleophiles proceeds regioselectively to give a series of new tri- and tetracyclic heterosystems, viz. derivatives of 5,6-dihydropyrazolo[1,5-a]pyrido[2,3-d]pyrimidin-6-one, 1,2-dihydropyrido[2,3-d]pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidin-2-one, 8,9-dihydro-5H-pyrido[2,3-d]thiazolo[3,2-a]pyrimidin-8-one, 1,2-dihydrobenzo[4,5]imidazo[1,2-a]pyrido[2,3-d]pyrimidin-2- one, and 1,2-dihydrobenzo[4,5] imidazo[1,2-g][1,6]naphthyridin-2-one.

  DOI：

  10.1007/s10593-008-0142-1

文献信息

• Recyclization of ethyl 1-alkyl-5-benzoyl-6-methylsulfanyl-2-oxo-1,2-dihydropyridine-3-carboxylates into Bicyclic N-alkyl-5-benzoyl-2-oxo-1,2-dihydropyridine-3-carboxamide derivatives by the action of nitrogen-containing 1,4- and 1,5-binucleophiles
  作者：V. N. Britsun、A. N. Esipenko、A. V. Gutov、A. N. Chernega、M. O. Lozinskii

  DOI：10.1134/s1070428009120148

  日期：2009.12

  Reactions of ethyl 1-alkyl-5-benzoyl-6-methylsulfanyl-2-oxo-1,2-dihydropyridine-3-carboxylates with nitrogen-containing 1,4- and 1,5-binucleophiles (o-phenylenediamine, o-aminobenzenethiol, ethane-1,2-diamine, and propane-1,3-diamine) involved recyclization, leading to the formation of fused N-alkyl-5-benzoyl- 2-oxo-1,2-dihydropyridine-3-carboxamides, diethyl 6,6'-oxybis(1-alkyl-5-benzoyl-2-oxo-1,2-dihydropyridine-3-carboxylates), and diethyl 6,6'-[ethane-1,2-diyl(or propane-1,3-diyl)diimino]bis(1-alkyl-5-benzoyl-2-oxo-1,2-dihydropyridine-3-carboxylates), depending on the reactant ratio. The sequence of formation of intermediate recyclization products was determined.
• Recyclization of 1-alkyl-5-benzoyl-3-ethoxycarbonyl-6-methylthio-1,2-dihydro-pyridin-2-ones into 1,6-annelated derivatives of 3-alkylcarbamoyl-5-benzoylpyridin-2-one
  作者：V. N. Britsun、A. N. Esipenko、A. V. Gootov、A. N. Chernega、M. O. Lozinskii

  DOI：10.1007/s10593-009-0284-9

  日期：2009.4

  For the first time the possibility has been shown of recyclizing 1-alkyl-5-benzoyl-3-ethoxycarbonyl-6-methylthio-1,2-dihydropyridin-2-ones into 1,6-annelated bicyclic derivatives of 3-alkylcarbamoyl-5-benzoylpyridin-2-one, which takes place on reacting the former with 1,4- and 1,5-nitrogen-containing dinucleophiles. The structure of the recyclization products was demonstrated by spectral methods and X-ray structural analysis.
• Heterocyclization of 3-(R-amino)-3-methylthio-1-phenylpropenones and 5-benzoyl-6-methylthio-1,2-dihydropyridin-2-ones with 1,2- and 1,3-dinucleophilic reagents
  作者：V. N. Britsun、N. V. Pikun、A. B. Ryabitskii、M. O. Lozinskii

  DOI：10.1007/s10593-011-0862-5

  日期：2011.11

  The interaction of 3-(R-amino)-3-methylthio-1-phenylpropenones and 1-alkyl-5-benzoyl-3-ethoxycarbonyl-6-methylthio-1,2-dihydropyridin-2-ones with N,N- and N, C-1,2- and 1,3-dinucleophiles proceeded regioselectively by [3+2] and [3+3] cyclocondensation with the formation of derivatives of pyrazole, benzimidazo[1,2-a]-pyridine, benzimidazo[1,2-a] pyrimidine, imidazo[1,2-a] pyrimidine, [1,2,4] triazolo[4,3-b]pyridazine, and 6,7-dihydro-2H-pyrazolo[3,4-b]pyridine. The regioselectivity of the reactions carried out was analyzed.
• Unusual reaction of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-r-1,2-dihydropyridin-2-ones with nitrogen-containing 1,4-dinucleophiles
  作者：V. N. Britsun、A. N. Esipenko、M. O. Lozinskii

  DOI：10.1007/s10593-008-0124-3

  日期：2008.7

  The reaction of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyridin-2-ones with the nitrogen-containing 1,4-dinucleophiles o-phenylenediamine, o-aminothiophenol, and ethylenediamine, proceeds as a recyclization, the products of which are derivatives of 5-(1H-benzimidazol-2-yl)-2H-2-pyranone, 5-(benzothiazol-2-yl)-2H-2-pyranone, and 5-(4,5-dihydro-1H-imidazol-2-yl)-2H-2-pyra-none respectively.
• Unusual reaction of 5-benzoyl-3-ethoxycarbonyl-6-methylthio-1-R-1,2-dihydropyridin-2-ones with 1,3-diaminopropane
  作者：V. N. Britsun、E. I. Mayboroda、M. O. Lozinskii

  DOI：10.1007/s10593-008-0054-0

  日期：2008.3