5-乙酰基-6-甲基-2-氧代-1,2-二氢-3-吡啶羧胺 | 52600-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 5-乙酰基-6-甲基-2-氧代-1,2-二氢-3-吡啶羧胺
• 英文名称: 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridine-carboxamide
• 英文别名: 6-Methyl-5-acetyl-1,2-dihydro-2-oxo-3-pyridinecarboxamide；5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarboxamide；5-acetyl-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid amide；5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinamide；5-Acetyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxamide；5-acetyl-6-methyl-2-oxo-1H-pyridine-3-carboxamide
• CAS: 52600-60-9
• 化学式: C₉H₁₀N₂O₃
• mdl: MFCD03425816
• 分子量: 194.19
• InChiKey: OHAQWEZPEZJQRK-UHFFFAOYSA-N

物化性质

• 熔点：
  325-327°C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  89.3
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  5-乙酰基-6-甲基-2-氧代-1,2-二氢-3-吡啶羧胺 在 硫酸 作用下， 以 水 为溶剂， 生成 5-乙酰基-6-甲基-2-氧代-1,2-二氢-3-吡啶羧酸
  参考文献：
  名称：

  5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their

  摘要：

  直链烷酰基)-6-(较低烷基)-2(1H)-吡啶酮(I)，作为心力衰竭药物，其中R.sub.2为氢或甲基，通过将2-(较低烷酰基)-1-(较低烷基)乙烯胺(II)与较低烷基2-丙炔酸酯或2-丁炔酸酯反应，或者通过水解4-R.sub.2-5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酸腈(III，其中Q为CN)或相应的4-R.sub.2-5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酰胺来制备相应的5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酸，并脱羧所述取代烟酸来产生I。还披露和声称了3-Q-4-R.sub.2-5-(较低烷酰基)-6-(较低烷基)-2(1H)-吡啶酮的心力衰竭用途，其中Q为氢或氰基，R.sub.2为氢或甲基(III)。还显示和声称了甲基4-乙酰基-5-氨基-2,4-己二烯酸酯或其酸盐，作为中间体或心力衰竭用药。

  公开号：

  US04524149A1
• 作为产物：
  描述：

  3-dimethylaminomethylenepentane-2,4-dione 在 硫酸 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 5-乙酰基-6-甲基-2-氧代-1,2-二氢-3-吡啶羧胺
  参考文献：
  名称：

  Mosti, Luisa; Schenone, Pietro; Menozzi, Giulia, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1503 - 1509

  摘要：

  DOI：

文献信息

• 5-(4-Thiazolyl)-6-alkyl-2(1H)-pyridinones and their cardiotonic use
  申请人：Sterling Drug Inc.

  公开号：US04469699A1

  公开（公告）日：1984-09-04

  3-Q-4-R.sub.2 -5-(2-Q'-5-R.sub.3 -4-thiazolyl)-6-R.sub.1 -2(1H)-pyridinones (I), where R.sub.1 is alkyl having from one to four carbon atoms, R.sub.2 is hydrogen or methyl, R.sub.3 is hydrogen or alkyl having from one to three carbon atoms, Q is amino, carbamyl, carboxy, cyano or hydrogen, and Q' is alkyl having from one to four carbon atoms, amino or R.sub.4 NH where R.sub.4 is alkyl having from one to four carbon atoms, or acid-addition salts thereof where at least one of Q and Q' is amino or Q' is R.sub.4 NH, are useful as cardiotonics (I where Q is amino, cyano or hydrogen) and/or as intermediates (I where Q is cyano, carbamyl or carboxy). Also shown as intermediates are 1,2-dihydro-4-R.sub.2 -5-[R.sub.3 CH(Br)CO]-6-R.sub.1 -2-oxo-3-pyridinecarbonitriles (II), and, also, processes for preparing I and II.

  3-Q-4-R.sub.2 -5-(2-Q'-5-R.sub.3 -4-thiazolyl)-6-R.sub.1 -2(1H)-pyridinones (I)，其中R.sub.1是具有一到四个碳原子的烷基，R.sub.2是氢或甲基，R.sub.3是氢或具有一到三个碳原子的烷基，Q是氨基、氨基甲酰基、羧基、氰基或氢，Q'是具有一到四个碳原子的烷基、氨基或R.sub.4 NH，其中R.sub.4是具有一到四个碳原子的烷基，或其酸盐加合物，其中Q和Q'中至少有一个是氨基或Q'是R.sub.4 NH，可用作心力补充剂（其中Q是氨基、氰基或氢）和/或作为中间体（其中Q是氰基、氨基甲酰基或羧基）。 还显示了1,2-二氢-4-R.sub.2 -5-[R.sub.3 CH(Br)CO]-6-R.sub.1 -2-氧代-3-吡啶腈（II）作为中间体，以及制备I和II的方法。
• Certain 2-(1H)-pyridinones cardiotonic compositions containing same and
  申请人：Sterling Drug Inc.

  公开号：US04415580A1

  公开（公告）日：1983-11-15

  1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (I, Q is hydrogen, hydroxy, amino, cyano or carbamyl) and/or intermediates therefor (I, Q is carboxy, aminocarbamyl, hydrogen, amino, cyano or carbamyl). Also shown are 3-Q"-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where R and R' are as above and Q' is hydrogen or cyano, which are useful as cardiotonics (II, Q' is hydrogen) and/or intermediates (II, Q' is cyano or hydrogen). Processes for preparing the compounds of formulas I and II are shown.

  1-R"-3-Q-4-R'-5-R-1,6-萘啶并[2(1H)-酮]（I）或其盐，其中R为低碳烷基，R'为氢或甲基，R"为氢或低碳烷基，Q为氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，可用作强心药剂（I，Q为氢、羟基、氨基、氰基或氨基甲酰基）和/或其中间体（I，Q为羧基、氨基甲酰基、氢、氨基、氰基或氨基甲酰基）。还显示了3-Q"-4-R'-5-(RCO)-6-[2-(二低碳烷基氨基)乙烯基]-2(1H)-吡啶酮（II）或其盐，其中R和R'如上所述，Q'为氢或氰基，可用作强心剂（II，Q'为氢）和/或其中间体（II，Q'为氰基或氢）。显示了制备式I和II化合物的方法。
• 5-Alkyl-1,6-naphthyridin-2(1H)-ones and cardiotonic use thereof
  申请人：Sterling Drug Inc.

  公开号：US04517190A1

  公开（公告）日：1985-05-14

  1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (I, Q is hydrogen, hydroxy, amino, cyano or carbamyl) and/or intermediates therefor (I, Q is carboxy, aminocarbamyl, hydrogen, amino, cyano or carbamyl). Also shown are 3-Q'-4-R'-5-(RCO)-6-[2-(di-lower-alkylamino)ethenyl]-2(1H)-pyridinones (II) or salts thereof, where R and R' are as above and Q' is hydrogen or cyano, which are useful as cardiotonics (II, Q' is hydrogen) and/or intermediates (II, Q' is cyano or hydrogen). Processes for preparing the compounds of formulas I and II are shown.

  1-R"-3-Q-4-R'-5-R-1,6-萘啉并吡啶-2(1H)-酮(I)或其盐，其中R为较低烷基，R'为氢或甲基，R"为氢或较低烷基，Q为氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，可用作强心药剂(I，Q为氢、羟基、氨基、氰基或氨基甲酰基)和/或其中间体(I，Q为羧基、氨基甲酰基、氢、氨基、氰基或氨基甲酰基)。还显示了3-Q'-4-R'-5-(RCO)-6-[2-(二次较低烷基氨基)乙烯基]-2(1H)-吡啶酮(II)或其盐，其中R和R'如上所述，Q'为氢或氰基，可用作强心剂(II，Q'为氢)和/或中间体(II，Q'为氰基或氢)。显示了制备式I和II化合物的方法。
• Process for preparing 5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinone
  申请人：Sterling Drug Inc.

  公开号：US04412077A1

  公开（公告）日：1983-10-25

  4-R.sub.2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R.sub.2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III, Q is CN) or corresponding 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R.sub.2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.

  4-R.sub.2 -5-(较低烷酰基)-6-(较低烷基)-2(1H)-吡啶酮（I），作为心力衰竭药物，其中R.sub.2为氢或甲基，通过将2-(较低烷酰基)-1-(较低烷基)乙烯胺（II）与较低烷基2-丙炔酸酯或2-丁炔酸酯分别反应或通过水解4-R.sub.2 -5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酰亚胺（III，其中Q为CN）或相应的4-R.sub.2 -5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酰胺来制备相应的5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酸，并脱羧所述取代烟酸产生I。还披露和声称3-Q-4-R.sub.2 -5-(较低烷酰基)-6-(较低烷基)-2(1H)-吡啶酮的心力衰竭用途，其中Q为氢或氰基，R.sub.2为氢或甲基（III）。还展示和声称4-乙酰基-5-氨基-2,4-己二烯酸甲酯或其酸盐，作为中间体或心力衰竭药物。
• 5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their
  申请人：Sterling Drug Inc.

  公开号：US04524149A1

  公开（公告）日：1985-06-18

  4-R.sub.2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R.sub.2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III), Q is CN) or corresponding 4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R.sub.2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R.sub.2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.

  直链烷酰基)-6-(较低烷基)-2(1H)-吡啶酮(I)，作为心力衰竭药物，其中R.sub.2为氢或甲基，通过将2-(较低烷酰基)-1-(较低烷基)乙烯胺(II)与较低烷基2-丙炔酸酯或2-丁炔酸酯反应，或者通过水解4-R.sub.2-5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酸腈(III，其中Q为CN)或相应的4-R.sub.2-5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酰胺来制备相应的5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酸，并脱羧所述取代烟酸来产生I。还披露和声称了3-Q-4-R.sub.2-5-(较低烷酰基)-6-(较低烷基)-2(1H)-吡啶酮的心力衰竭用途，其中Q为氢或氰基，R.sub.2为氢或甲基(III)。还显示和声称了甲基4-乙酰基-5-氨基-2,4-己二烯酸酯或其酸盐，作为中间体或心力衰竭用药。