6-(2-dimethylaminoethenyl)-5-(n-propanoyl)-2(1H)-pyridinone | 88877-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(2-dimethylaminoethenyl)-5-(n-propanoyl)-2(1H)-pyridinone
• 英文别名: 6-[(E)-2-(dimethylamino)ethenyl]-5-propanoyl-1H-pyridin-2-one
• CAS: 88877-01-4
• 化学式: C₁₂H₁₆N₂O₂
• 分子量: 220.271
• InChiKey: BZIPNNJQDMWXAO-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-dimethylaminoethenyl)-5-(n-propanoyl)-2(1H)-pyridinone 在 盐酸 作用下， 以77%的产率得到5-hydroxy-6-methylquinolin-2(1H)-one
  参考文献：
  名称：

  Novel Synthesis of 1,6-Naphthyridin-2(6H)-ones, Quinolin-2(1H)-ones, and Quino[7,8-f]quinoline-2,9(1H,10H)-dione from Common Precursors

  摘要：

  1,6-萘啶-2(6H)-酮 3、喹啉-2(1H)-酮 5 和喹啉并[7,8-f]喹啉-2,9(1H,10H)-二酮 10 是由 5-酰基-6-[2-（二甲基氨基）乙烯基]吡啶-2(1H)-酮 1 合成的。

  DOI：

  10.1055/s-1992-26090
• 作为产物：
  描述：

  6-methyl-5-(n-propanoyl)-2(1H)-pyridinone 、 N,N-二甲基甲酰胺二甲基缩醛 以 N-甲基乙酰胺 、 乙醇 为溶剂， 生成 6-(2-dimethylaminoethenyl)-5-(n-propanoyl)-2(1H)-pyridinone
  参考文献：
  名称：

  5-(Hydroxyalkyl or alkanoyloxymethyl)-1,6-naphthyridin-2(1H)-one and

  摘要：

  4-R'-5-Q-1,6-萘啶并[2(1H)-酮] (I)，其中R'为氢或甲基，Q为羟甲基，1-羟乙基烷酰氧甲基或1-烷酰氧乙基，首先将4-R'-5-乙酰基（或正丙酰基）-6-[2-(二低烷基)氨基]-2(1H)-吡啶酮[III]与羟胺或其盐反应，生成4-R'-5-Q'-1,6-萘啶并[2(1H)-酮]-6-氧化物(II)，其中R'如上所述，Q'为甲基或乙基；然后用脂肪酸酐反应II，生成Q为烷酰氧甲基或1-烷酰氧乙基的I；然后水解所述的烷酰氧甲基或烷酰氧乙基化合物，生成Q为羟甲基或1-羟乙基的I。还显示了II和Q为羟甲基，1-羟乙基或烷酰氧甲基的I的强心作用。

  公开号：

  US04532247A1

文献信息

• 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-(Hydroxyalkyl or alkanoyloxymethyl)-1,6-naphthyridin-2(1H)-one and
  申请人：Sterling Drug Inc.

  公开号：US04532247A1

  公开（公告）日：1985-07-30

  4-R'-5-Q-1,6-naphthyridin-2(1H)-ones (I), where R' is hydrogen or methyl and Q is hydroxymethyl, 1-hydroxyethyl alkanoyloxymethyl or 1-alkanoyloxyethyl, are produced by first reacting 4-R'-5-acetyl(or n-propanoyl)-6-[2-(di-lower-alkylamino]-2(1H)-pyridinone [III] with hydroxylamine or salt thereof to produce 4-R'-5-Q'-1,6-naphthyridin-2(1H)-one-6-oxide (II), where R' is defined as above and Q' is methyl or ethyl; next reacting II with an alkanoic anhydride to produce I where Q is alkanoyloxymethyl or 1-alkanoyloxyethyl; and, then hydrolyzing said alkanoyloxymethyl or -ethyl compound to produce I where Q is hydroxymethyl or 1-hydroxyethyl. Also shown is the cardiotonic use of II and I where Q is hydroxymethyl, 1-hydroxyethyl or alkanoyloxymethyl.

  4-R'-5-Q-1,6-萘啶并[2(1H)-酮] (I)，其中R'为氢或甲基，Q为羟甲基，1-羟乙基烷酰氧甲基或1-烷酰氧乙基，首先将4-R'-5-乙酰基（或正丙酰基）-6-[2-(二低烷基)氨基]-2(1H)-吡啶酮[III]与羟胺或其盐反应，生成4-R'-5-Q'-1,6-萘啶并[2(1H)-酮]-6-氧化物(II)，其中R'如上所述，Q'为甲基或乙基；然后用脂肪酸酐反应II，生成Q为烷酰氧甲基或1-烷酰氧乙基的I；然后水解所述的烷酰氧甲基或烷酰氧乙基化合物，生成Q为羟甲基或1-羟乙基的I。还显示了II和Q为羟甲基，1-羟乙基或烷酰氧甲基的I的强心作用。
• 5-Alkyl-1,6-naphthyridin-2(1H)-ones, intermediates, their preparation and their cardiotonic use
  申请人：STERLING DRUG INC.

  公开号：EP0101952A1

  公开（公告）日：1984-03-07

  Naphthyridines of formula (I) , where R is -alkyl, R' is hydrogen or methyl, R" is hydrogen or alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic agents (1, 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 pyridinones of formula II 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.

  式(I)的萘啶类化合物 其中 R 为烷基，R'为氢或甲基，R "为氢或烷基，Q 为氢、羟基、氨基、氰基、氨甲酰、羧基或氨基甲酰，可用作强心剂（1，Q 为氢、羟基、氨基、氰基或氨基甲酰）和/或其中间体（I，Q 为羧基、氨基甲酰、氢、氨基、氰基或氨基甲酰）。图中还显示了式 II 的吡啶酮类化合物 其中 R 和 R'如上，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）。所示为制备式 I 和 II 化合物的工艺。
• 1,6-Naphthyridin derivatives useful as cardiotonics and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0134535A1

  公开（公告）日：1985-03-20

  4-R'-5-Q-1,6-naphthyridin-2(1H)-ones (I), where R' is . hydrogen or methyl and Q is hydroxymethyl, 1-hydroxyethyl alkanoyloxymethyl or 1-alkanoyloxyethyl, are produced by first reacting 4-R'-5-acetyl (or n-propanoyl)-6-[2-(di- lower-alkylamino]-2(1H)-pyridinone (III) with hydroxylamine or salt thereof to produce 4-R'-5-Q'-1,6-naphthyridin-2(1H)-one-6-oxide (II), where R' is defined as above and Q' is methyl or ethyl; next reacting II with an alkanoic anhydride to produce I where Q is alkanoyloxymethyl or 1- alkanoyloxyethyl; and, then hydrolyzing said alkanoyloxymethyl or -ethyl compound to produce I where Q is hydroxymethyl or 1-hydroxyethyl. Also shown is the cardiotonic use of II and I where Q is hydroxymethyl, 1-hydroxyethyl or alkanoyloxymethyl.

  4-R'-5-Q-1,6-萘啶-2(1H)-酮 (I)，其中 R' 是 .氢或甲基，Q 为羟甲基、1-羟乙基烷酰氧基甲基或 1-烷酰氧基乙基、首先将 4-R'-5-乙酰基（或正丙酰基）-6-[2-（二低级烷基氨基）-2(1H)-吡啶酮（III）]与羟胺或其盐反应，生成 4-R'-5-Q'-1,6-萘啶-2(1H)-酮-6-氧化物（II），其中 R'定义如上，Q'为甲基或乙基；再将 II 与烷酸酐反应生成 I，其中 Q 为烷酰氧基甲基或 1-烷酰氧基乙基；然后，水解所述烷酰氧基甲基或-乙基化合物，生成 I，其中 Q 为羟甲基或 1-羟乙基。图中还显示了 II 和 I 的强心剂用途，其中 Q 为羟甲基、1-羟乙基或烷酰氧基甲基。
• US4415580A
  申请人：——

  公开号：US4415580A

  公开（公告）日：1983-11-15