4-(pyridin-4-yl)-4-oxobutanenitrile | 49835-53-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(pyridin-4-yl)-4-oxobutanenitrile
• 英文别名: 3-Isonicotinoylpropionitril；γ-oxo-γ-(4-pyridinyl)butyronitrile；4-oxo-4-(4-pyridinyl)butanenitrile；4-oxo-4-pyridin-4-yl-butyronitrile；4-Oxo-4-pyridin-4-ylbutanenitrile
• CAS: 49835-53-2
• 化学式: C₉H₈N₂O
• 分子量: 160.175
• InChiKey: UTISRGMYIPHHBR-UHFFFAOYSA-N

物化性质

• 熔点：
  49-52 °C
• 沸点：
  361.7±22.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(pyridin-4-yl)-4-oxobutanenitrile 生成 4,5-Dihydro-6-(pyridin-4-yl)-pyridazin-3(2H)-one
  参考文献：
  名称：

  LESHER, G. Y.;DICKINSON, W. B.

  摘要：

  DOI：
• 作为产物：
  描述：

  4-吡啶甲醛 以 氯仿 、 乙腈 为溶剂， 生成 4-(pyridin-4-yl)-4-oxobutanenitrile
  参考文献：
  名称：

  3-Hydrazino-6-(pyridinyl) pyridazines and cardiotonic use thereof

  摘要：

  3-肼基-6-PY-吡啶嗪或其药学上可接受的酸加成盐在心脏强心剂中有用，其中PY是4-或3-吡啶基或4-或3-吡啶基有一个或两个较低烷基取代基。通过将6-PY-3-吡啶嗪与氯化剂反应以产生3-氯-6-PY-吡啶嗪，再将所述3-氯化合物与肼反应以产生所述3-肼基化合物来制备6-PY-3-吡啶醇。本发明披露了3-肼基-6-PY-吡啶嗪或其药学上可接受的酸加成盐作为增加心脏收缩力的心脏强心剂组成物的活性成分，并用于增加需要此类治疗的患者的心脏收缩力的方法。新型中间体3-氯-6-PY-吡啶嗪如上所述制备。

  公开号：

  US04304775A1

文献信息

• 1-Butyl-3-methylimidazolium Bromide as a Solvent and Precatalyst for Stetter Reaction
  作者：Baramee Phungpis、Viwat Hahnvajanawong

  DOI：10.14233/ajchem.2020.22711

  日期：——

  Stetter reaction between aromatic aldehydes and acrylonitrile/ethyl acrylate performing in [Bmim]Br in the presence of NaOH is described. N-Heterocyclic carbene (NHC) generates in situ is shown to be an efficient catalyst. Benzoin condensation also occured as side reaction.

  芳香醛和丙烯腈/丙烯酸乙酯在[Bmim]Br存在NaOH的情况下进行的Stetter反应被描述。显示了原位生成的N-杂环卡宾（NHC）是一种高效的催化剂。苯甲醇缩合也作为副反应发生。
• 4-Substituted-6-(pyridinyl)-3(2h)-pyridazinones and their use as
  申请人：Sterling Drug Inc.

  公开号：US04304776A1

  公开（公告）日：1981-12-08

  2-R-4-R'-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as intermediates and some as cardiotonics, are prepared by reacting di-(lower-alkyl) hydroxy[2-oxo-2-PY-ethyl]propanedioate (II) with a hydrazine salt of the formula RNHNH.sub.2.nH.sub.x An (III) to produce lower-alkyl 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylate (Ia where R' is lower-carbalkoxy) and reacting Ia with hydrazine hydrate or anhydrous hydrazine to produce 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (Ib where R' is aminocarbamyl), where PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, R is hydrogen, lower-alkyl or lower-hydroxyalkyl, R' is carbamyl, carboxy, aminocarbamyl or lower-carbalkoxy, n is 1 or 2, x is 1, 2 or 3, and An is an anion of a strong inorganic acid or an organic sulfonic acid. Also shown are: the preparation of II from PY--COCH.sub.3 (IV), the conversion of Ia to Ib (Id where R' is carboxy), and the use of 2-R-4-R"-6-PY-3(2H)-pyridazinones (I where R is lower-alkyl or lower-hydroxyalkyl and R" is carbamyl, aminocarbamyl or lower-carbalkoxy) as cardiotonic agents. Other intermediates are shown.

  2-R-4-R'-6-PY-3(2H)-吡啶并咪唑酮（I）或其盐，可作为中间体和一些作为心脏强心剂，通过将二（较低烷基）羟基[2-氧代-2-PY-乙基]丙二酸酯（II）与公式RNHNH.sub.2.nH.sub.x An（III）的肼盐反应制备，以产生较低烷基2,3-二氢-2-R-3-氧代-6-PY-4-吡啶并咪唑羧酸酯（Ia，其中R'为较低碳烷氧基），并将Ia与肼水合物或无水肼反应，以产生2,3-二氢-2-R-3-氧代-6-PY-4-吡啶并咪唑羧酸肼（Ib，其中R'为氨基羰基），其中PY为4-或3-吡啶基或带有一个或两个较低烷基取代基的4-或3-吡啶基，R为氢、较低烷基或较低羟基烷基，R'为羰基、羧基、氨基羰基或较低碳烷氧基，n为1或2，x为1、2或3，An为强无机酸或有机磺酸的阴离子。还显示了：从PY--COCH.sub.3（IV）制备II，将Ia转化为Ib（其中R'为羧基），以及将2-R-4-R"-6-PY-3(2H)-吡啶并咪唑酮（I，其中R为较低烷基或较低羟基烷基，R"为羰基、氨基羰基或较低碳烷氧基）用作心脏强心剂。还显示了其他中间体。
• 4-Amino-6-(pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics
  申请人：Sterling Drug Inc.

  公开号：US04305943A1

  公开（公告）日：1981-12-15

  4-Amino-2-R-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as cardiotonics, where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents are prepared by: (a) reaction of 2-R-6-PY-3(2H)-pyridazinone (II) with hydrazine; (b) conversion from 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxamide (III); or, (c) conversion form 2,3-dihydro-2-R-3-oxo-6-PY-4-pyridazinecarboxylic acid hydrazide (IV). Also shown are: the use of I or salts as cardiotonic agents; and, the preparation of intermediates.

  4-氨基-2-R-6-PY-3(2H)-吡啶并嗪酮(I)或其盐，可用作心力衰竭药物，其中R为氢、低烷基或低羟基烷基，PY为4-或3-吡啶基或带有一个或两个低烷基取代基的4-或3-吡啶基，通过以下方法制备：(a) 2-R-6-PY-3(2H)-吡啶并嗪酮(II)与肼的反应；(b) 从2,3-二氢-2-R-3-氧代-6-PY-4-吡啶并嗪甲酰胺(III)转化而来；或(c) 从2,3-二氢-2-R-3-氧代-6-PY-4-吡啶并嗪羧酸肼酰肼(IV)转化而来。还显示了：将I或其盐用作心力衰竭药物；以及中间体的制备。
• 4,5-Dihydro-2-methyl-6-(4-pyridinyl)-3(2H)-pyridazinone and its use as a
  申请人：Sterling Drug Inc.

  公开号：US04337253A1

  公开（公告）日：1982-06-29

  2-R-4,5-dihydro-4-R'-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as cardiotonics, where R is lower-alkyl or lower-hydroxyalkyl, R' is hydrogen or lower-alkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, are prepared by reacting 4-oxo-4-PY-2-R'-butanenitrile with an N-R-hydrazine salt of a strong inorganic acid or organic sulfonic acid or by reacting a lower-alkyl 4-oxo-4-PY-2-R'-butanoate or lower-alkyl 4-(BN)-4-cyano-4-PY-2-R'-butanoate with N-R-hydrazine where BN is 4-morpholinyl, 1-piperidinyl or 1-pyrrolidinyl. Also shown are: (a) cardiotonic compositions and a method for increasing cardiac contractility using said compounds or salts where R is lower-alkyl (b) the use of I as intermediates in preparing the corresponding 2-R-4-R'-6-PY-3(2H)-pyridazinones; and, (c) the preparation of said lower-alkyl 4-(BN)-4-cyano-4-PY-2-R'-butanoates.

  本发明涉及2-R-4,5-二氢-4-R'-6-PY-3(2H)-吡啶嗪酮(I)或其盐，其可用作心脏强心剂，其中R为低烷基或低羟基烷基，R'为氢或低烷基，PY为4-或3-吡啶基或具有一或两个低烷基取代基的4-或3-吡啶基，通过将4-氧代-4-PY-2-R'-丁腈与强无机酸或有机磺酸的N-R-腙盐反应，或通过将低烷基4-氧代-4-PY-2-R'-丁酸酯或低烷基4-(BN)-4-氰基-4-PY-2-R'-丁酸酯与N-R-腙反应，其中BN为4-吗啉基，1-哌啶基或1-吡咯烷基，制备所述化合物。还显示了：(a)心脏强心剂组合物和使用具有R为低烷基的化合物或其盐来增加心脏收缩力的方法(b)将I用作制备相应的2-R-4-R'-6-PY-3(2H)-吡啶嗪酮的中间体；以及(c)制备所述低烷基4-(BN)-4-氰基-4-PY-2-R'-丁酸酯。
• 6-(Pyridinyl)-3(2H)-pyridazinones and their use as cardiotonics
  申请人：Sterling Drug Inc.

  公开号：US04304777A1

  公开（公告）日：1981-12-08

  2-R-6-PY-3(2H)-pyridazinones (I) or salts thereof, which are useful as cardiotonics, where R is hydrogen, lower-alkyl or lower-hydroxyalkyl, and PY is 4- or 3-pyridinyl or 4- or 3-pyridinyl having one or two lower-alkyl substituents, are prepared by reacting 2-R-4,5-dihydro-6-PY-3(2H)-pyridazinone with a dehydrogenating agent. Also shown are: cardiotonic compositions and a method for increasing cardiac contractility using I or salts; and, the preparation of the corresponding intermediate 4,5-dihydro compounds.

  2-R-6-PY-3(2H)-pyridazinones (I)或其盐是有用的心脏强心剂，其中R是氢，低碳基或低羟基碳基，PY是4-或3-吡啶基或4-或3-吡啶基，具有一个或两个低碳基取代基，通过将2-R-4,5-二氢-6-PY-3(2H)-吡啶嗪与脱氢剂反应制备。还显示了：使用I或其盐的心脏强心剂组合物和增强心肌收缩力的方法；以及制备相应的中间体4,5-二氢化合物。