5-Acetyl-6-methyl-3,4-dihydro-2-pyridon | 13729-69-6

• 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
• 英文名称: 5-Acetyl-6-methyl-3,4-dihydro-2-pyridon
• 英文别名: 5-acetyl-3,4-dihydro-6-methyl-2(1H)-pyridinone；5-acetyl-6-methyl-3,4-dihydro-1H-pyridin-2-one
• CAS: 13729-69-6
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: ZYRYXEYNFDAQCY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Acetyl-6-methyl-3,4-dihydro-2-pyridon 在 palladium on activated charcoal 作用下， 反应 0.33h， 以49%的产率得到5-乙酰基-6-甲基-2(1H)-吡啶酮
  参考文献：
  名称：

  Kato, Tetsuzo; Sato, Masayuki; Wagai, Akihiro, Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 603 - 606

  摘要：

  DOI：
• 作为产物：
  描述：

  4-Aminopent-3-en-2-one 、 丙烯酰氯 以 四氢呋喃 为溶剂， 生成 5-Acetyl-6-methyl-3,4-dihydro-2-pyridon
  参考文献：
  名称：

  Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the selective reduction of acylated enaminones

  摘要：

  A convenient methodology for the stereoselective preparation of 5-alkyliden-6-aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2-pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3, an accessible starling material obtained by mild and selective reduction of the 5-acyltetrahydro-2-pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2-pyranone 4 was investigated and rationalized. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10333-7

文献信息

• 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)是一种有益的心力衰竭药物，其中R.sub.2为氢或甲基。该药物的制备方法是将2-(较低烷酰基)-1-(较低烷基)乙烯胺(II)分别与较低烷基2-丙炔酸酯或2-丁炔酸酯反应，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-氧基烟酰胺产生相应的5-(较低烷酰基)-6-(较低烷基)-1,2-二氢-2-氧基烟酸，然后脱羧该取代烟酸产生I。此外，还揭示和声明了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，R.sub.2为氢或甲基(III)。同时还显示和声明了4-乙酰基-5-氨基-2,4-己二烯酸甲酯或其酸盐加成物，可用作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.

  4-R.sub.2 -5-(低碳酰基)-6-(低烷基)-2(1H)-吡啶酮(I)是一种有益于心脏的强心剂，其中R.sub.2为氢或甲基，通过将2-(低碳酰基)-1-(低烷基)乙烯胺(II)分别与低烷基2-丙炔酸酯或2-丁炔酸酯反应或通过水解4-R.sub.2-5-(低碳酰基)-6-(低烷基)-1,2-二氢-2-氧基烟酰腈(III)(其中Q为CN)或相应的4-R.sub.2-5-(低碳酰基)-6-(低烷基)-1,2-二氢-2-氧基烟酰胺以产生相应的5-(低碳酰基)-6-(低烷基)-1,2-二氢-2-氧基烟酸，并脱羧化所述取代烟酸酸以产生I。还揭示和声明了3-Q-4-R.sub.2-5-(低碳酰基)-6-(低烷基)-2(1H)-吡啶酮的强心剂用途，其中Q为氢或氰，R.sub.2为氢或甲基(III)。还显示和声明了甲基4-乙酰基-5-氨基-2,4-己二烯酸酯或其酸盐加成物，可用作中间体或强心剂。
• 5-(Phenyl)-1,6-naphthyridin-2(1H)-ones, their cardiotonic use and
  申请人：Sterling Drug Inc.

  公开号：US04560691A1

  公开（公告）日：1985-12-24

  1-R-5-Ar-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is hydrogen or methyl, and Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, hydroxy, amino, acetylamino, methanesulfonylamino, bromo, chloro, fluoro, cyano or carbamyl are useful as cardiotonic agents and corresponding compounds where Ar is nitrophenyl are useful as intermediates. Also shown as intermediates, are 5-(Ar--CO)-6-[2-(di-lower-alkylamino)-ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, cyano or nitro and 5-(Ar--CO)-6-methyl-2(1H)-pyridinones (III) where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, hydroxy, cyano or nitro; said compounds (III) where Ar is phenyl or hydroxyphenyl also are useful as cardiotonic agents. Processes for preparing the compounds of formulas I, II and III are shown.

  1-R-5-Ar-1,6-萘啶并[2(1H)-酮]（I）或其盐，其中R为氢或甲基，Ar为苯基或被甲基、乙基、甲氧基、乙氧基、羟基、氨基、乙酰氨基、甲磺酰氨基、溴、氯、氟、氰或氨基甲酰基取代的苯基，可用作心力增强剂，其中Ar为硝基苯基的相应化合物可用作中间体。还显示了5-(Ar-CO)-6-[2-(二低烷基氨基)-乙烯基]-2(1H)-吡啶酮（II）或其盐，其中Ar为苯基或被甲基、乙基、甲氧基、乙氧基、溴、氯、氟、氰或硝基取代的苯基，以及5-(Ar-CO)-6-甲基-2(1H)-吡啶酮（III），其中Ar为苯基或被甲基、乙基、甲氧基、乙氧基、溴、氯、氟、羟基、氰或硝基取代的苯基；其中Ar为苯基或羟基苯基的化合物（III）也可用作心力增强剂。显示了制备公式I、II和III化合物的过程。
• Alkanoylpyridinones useful as cardiotonics and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0089022A2

  公开（公告）日：1983-09-21

  3-Q-4-R2-5-(Lower-alkanoyl)-6-(lower-alkyt)-2(1H)-pyridinones (I), useful as cardiotonics, where Q is hydrogen or cyano, R2 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-R2-5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2- oxonicotinonitrile or corresponding 4-R2-5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotonic acid and decarboxylating said substituted nicotinic acid to produce I. Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiontonic.

  3-Q-4-R2-5-(低级烷酰基)-6-(低级烷基)-2(1H)-吡啶酮 (I)，可用作强心剂，其中 Q 为氢或氰基，R2 为氢或甲基、分别通过 2-(低级烷酰基)-1-(低级烷基)乙烯胺 (II) 与低级烷基 2-丙炔酸酯或 2-丁炔酸酯反应，或通过水解 4-R2-5-(低级烷酰基)-6-(低级烷基)-1、或相应的 4-R2-5-(低级烷酰基)-6-(低级烷基)-1,2-二氢-2-氧代烟酰胺水解生成相应的 5-(低级烷酰基)-6-(低级烷基)-1,2-二氢-2-氧代烟酸，并将所述取代的烟酸脱羧生成 I。图中还显示并要求得到 4-乙酰基-5-氨基-2,4-己二烯酸甲酯或其酸加成盐，可用作中间体或心酮酸。
• 1-6-Naphthyridin-2(1H)-ones useful as cardiotonics
  申请人：STERLING DRUG INC.

  公开号：EP0168037A2

  公开（公告）日：1986-01-15

  1-R-5-Ar-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is hydrogen or methyl, and Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, hydroxy, amino, acetylamino, methanesulfonylamino, bromo, chloro, fluoro, cyano or carbamyl are useful as cardiotonic agents and corresponding compounds where Ar is nitrophenyl are useful as intermediates. Also shown as intermediates, are 5-(Ar-CO)-6-[2-(di-lower-alkylamino)-ethenyl]-2(1H)-pyridinones (II) or salts thereof, where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, cyano or nitrp and 5-(Ar-CO)-6-methyl-2(1H)-pyridinones (III) where Ar is phenyl or phenyl substituted by methyl, ethyl, methoxy, ethoxy, bromo, chloro, fluoro, hydroxy, cyano or nitro; said compounds (III) where Ar is phenyl or hydroxyphenyl also are useful as cardiotonic agents. A process for preparing the compounds of formula I, comprises reacting compound (11) with formamidine or ammonia or a salt thereof.

  1-R-5-Ar-1,6-萘啶-2(1H)-酮(I)或其盐，其中 R 为氢或甲基，Ar 为苯基或被甲基、乙基、甲氧基、乙氧基、羟基、氨基、乙酰氨基、甲磺酰氨基、溴基、氯基、氟基、氰基或氨甲酰取代的苯基，可用作强心剂，Ar 为硝基苯基的相应化合物可用作中间体。作为中间体的还有 5-(Ar-CO)-6-[2-(二低烷基氨基)-乙烯基]-2(1H)-吡啶酮 (II) 或其盐，其中 Ar 是苯基或被甲基、乙基、甲氧基、乙氧基、溴基、氯基、氟基、氰基取代的苯基、和 5-(Ar-CO)-6-甲基-2(1H)-吡啶酮 (III)，其中 Ar 为苯基或被甲基、乙基、甲氧基、乙氧基、溴基、氯基、氟基、羟基、氰基或硝基取代的苯基；Ar 为苯基或羟基苯基的所述化合物（III）也可用作强心剂。制备式 I 化合物的工艺包括使化合物 (11) 与甲脒或氨或其盐反应。