3-((dimethylamino)methylene)hexane-2,4-dione | 88302-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-((dimethylamino)methylene)hexane-2,4-dione
• 英文别名: 3-[(Dimethylamino)methylidene]hexane-2,4-dione；3-(dimethylaminomethylidene)hexane-2,4-dione
• CAS: 88302-03-8
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: KOIAGXAXVITXID-UHFFFAOYSA-N

物化性质

• 沸点：
  288.3±35.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-((dimethylamino)methylene)hexane-2,4-dione 、 氰乙酰胺 、 sodium methylate 在 甲醇 、 水 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以to yield 7.8 g of 1,2-dihydro-6-methyl-2-oxo-5-(n-propanoyl)-3-pyridinecarbonitrile, m.p. 265°-268° C. with decomposition的产率得到1,2-dihydro-6-methyl-2-oxo-5-(n-propanoyl)-3-pyridinecarbonitrile
  参考文献：
  名称：

  5-.alpha.-bromoalkanoyl-2-oxo-3-pyridinecarbonitriles

  摘要：

  3-Q-4-R.sub.2 -5-(2-Q'-5-R.sub.3 -4-噻唑基)-6-R.sub.1 -2(1H)-吡啶酮(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，或其酸加成盐，其中至少有一个Q和Q'是氨基或Q'是R.sub.4 NH，可用作心脏强心剂（当Q为氨基，氰基或氢时的I）和/或中间体（当Q为氰基，氨基甲酰基或羧基时的I）。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-吡啶基腈（II）作为中间体，并且还提供了制备I和II的方法。

  公开号：

  US04595762A1
• 作为产物：
  描述：

  2,4-己二酮 、 N,N-二甲基甲酰胺二甲基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以to yield, as a liquid, 3-dimethylaminomethylene-2,4-hexanedione的产率得到3-((dimethylamino)methylene)hexane-2,4-dione
  参考文献：
  名称：

  5-.alpha.-bromoalkanoyl-2-oxo-3-pyridinecarbonitriles

  摘要：

  3-Q-4-R.sub.2 -5-(2-Q'-5-R.sub.3 -4-噻唑基)-6-R.sub.1 -2(1H)-吡啶酮(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，或其酸加成盐，其中至少有一个Q和Q'是氨基或Q'是R.sub.4 NH，可用作心脏强心剂（当Q为氨基，氰基或氢时的I）和/或中间体（当Q为氰基，氨基甲酰基或羧基时的I）。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-吡啶基腈（II）作为中间体，并且还提供了制备I和II的方法。

  公开号：

  US04595762A1

文献信息

• [EN] PYRIDINONE- AND PYRIDAZINONE-BASED COMPOUNDS AND MEDICAL USES THEREOF<br/>[FR] COMPOSÉS À BASE DE PYRIDINONE ET DE PYRIDAZINONE ET UTILISATIONS MÉDICALES ASSOCIÉES
  申请人：HLA TIMOTHY

  公开号：WO2019173790A1

  公开（公告）日：2019-09-12

  The various examples presented herein are directed to compounds of the formula A-L1-Het1-L2-Cy1 or a pharmaceutical acceptable salt, polymorph, prodrug, solvate or clathrate thereof, wherein: A is cycloalkyl, aryl, arylalkyl or heterocyclyl; Het1 is heterocyclyl containing at least two heteroatoms; Cy1 is a heterocyclyl; L1 is a bond, alkyl, alkenyl or alkynyl linker; L2 is an acyl or alkyl linker; and A and Cy1 are different. The compounds are useful in the treatment of fibrotic diseases, abnormal vascular leak and pathological angiogenesis.

  本文提供的各种示例涉及到以下公式的化合物A-L1-Het1-L2-Cy1或其药用可接受的盐、多型体、前药、溶剂合物或包合物，其中：A为环烷基、芳基、芳基烷基或杂环烷基；Het1为含有至少两个杂原子的杂环烷基；Cy1为杂环烷基；L1为键、烷基、烯基或炔基连接物；L2为酰基或烷基连接物；A和Cy1不同。这些化合物在治疗纤维化疾病、异常血管渗漏和病理性血管生成方面具有用途。
• 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为低碳基，R'为氢或甲基，R"为氢或低碳基，Q为氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，可作为心力衰竭药物（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，可作为心力衰竭药物（II，Q'为氢）和/或其中间体（II，Q'为氰基或氢）。显示了制备I和II式化合物的过程。
• 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-(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-噻唑基)-6-R.sub.1 -2(1H)-吡啶酮(I)，其中R.sub.1是具有一至四个碳原子的烷基，R.sub.2是氢或甲基，R.sub.3是氢或具有一至三个碳原子的烷基，Q是氨基，氨基甲酰基，羧基，氰基或氢，而Q'是具有一至四个碳原子的烷基，氨基或R.sub.4 NH，其中R.sub.4是具有一至四个碳原子的烷基，或它们的酸加成盐，其中至少有一个Q和Q'为氨基或Q'为R.sub.4 NH，可用作心脏强心剂（其中Q为氨基，氰基或氢）和/或中间体（其中Q为氰基，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-吡啶基腈(II)作为中间体，以及制备I和II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-萘啶并[2(1H)-酮]（I）或其盐，其中R为低碳基，R'为氢或甲基，R"为氢或低碳基，Q为氢、羟基、氨基、氰基、氨基甲酰基、羧基或氨基甲酰基，作为强心剂（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）有用。还显示了3-Q'-4-R'-5-(RCO)-6-[2-(二低碳基氨基)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，它们作为强心剂（II，Q'为氢）和/或中间体（II，Q'为氰基或氢）有用。显示了制备公式I和II化合物的过程。