3-(4-nitrophenyl)-1-methyl-3-oxo-1-propenamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-nitrophenyl)-1-methyl-3-oxo-1-propenamine
• 英文别名: (Z)-3-amino-1-(4-nitrophenyl)but-2-en-1-one
• 化学式: C₁₀H₁₀N₂O₃
• 分子量: 206.201
• InChiKey: HRHPQDLRRMZGNI-SREVYHEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  88.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-nitrophenyl)-1-methyl-3-oxo-1-propenamine 在 Montmorillonite K₁₀ 、 盐酸羟胺 作用下， 反应 3.0h， 以99%的产率得到3-(4-nitro-phenyl)-5-methylisoxazole
  参考文献：
  名称：

  使用K-10 /超声波检测对苯基取代的β-烯胺化合物的反应性。II †。异恶唑和5-异恶唑酮的合成

  摘要：

  以K-10为固体载体，超声处理4-苯基取代的β-烯胺酮1a-d和β-烯胺酯5a-d与盐酸羟胺的缩合反应，以评价β中异恶唑环和5-异恶唑酮环的形成。 -具有取代的芳环的-烯氨基化合物。得到异恶唑2a-c，3c-d和5-异恶唑酮6a-c和7a-d。在某些情况下，在该反应中使用K-10 /超声波可提供新颖的结果。

  DOI：

  10.1002/jhet.5570360229
• 作为产物：
  描述：

  1-(4-硝基苯基)丁烷-1,3-二酮 在 montmorillonite K-10 、 氨 、 水 作用下， 反应 10.0h， 以78%的产率得到3-(4-nitrophenyl)-1-methyl-3-oxo-1-propenamine
  参考文献：
  名称：

  The Use of K-10/Ultrasound in the Selective Synthesis of Unsymmetrical β-Enamino Ketones

  摘要：

  DOI：

  10.1055/s-1998-2107

文献信息

• 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均可作为强心药剂，相应的Ar为硝基苯基时可作为中间体。还显示了5-(Ar--CO)-6-[2-(二低碳基氨基)-乙烯基]-2(1H)-吡啶酮（II）或其盐作为中间体，其中Ar为苯基或甲基、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为苯基或甲基、乙基、甲氧基、乙氧基、溴、氯、氟、羟基、氰或硝基；当Ar为苯基或羟基苯基时，化合物（III）也可作为强心药剂。显示了制备式I、II和III化合物的方法。
• Reactions of Methyl Ketones and (Hetero)arylcarboxamides with N,N-Dimethylacetamide Dimethyl Acetal. A Simple Metal-Free Synthesis of 2,4,6-Trisubstituted Pyridines
  作者：Benjamin Prek、Uroš Grošelj、Marta Kasunič、Silvo Zupančič、Jurij Svete、Branko Stanovnik

  DOI：10.1071/ch14349

  日期：——

  Two metal-free syntheses of 2,4,6-trisubstituted pyridines 10a–m and 16a–j are described. N,N,6-Trimethyl-4-(substituted)pyridin-2-amines 10 were prepared from aryl or heteroaryl methyl ketones which were transformed with N,N-dimethylacetamide dimethyl acetal (DMADMA) into enaminones 4a–m, followed by treatment with ammonium acetate to give (Z)-3-amino-1-(substituted)but-2-en-1-ones 5a–m. These were

  描述了2,4,6-三取代的吡啶10a - m和16a - j的两种无金属合成方法。由芳基或杂芳基甲基酮制备N，N，6-，三甲基-4-（取代）吡啶-2-胺10，然后用N，N-二甲基乙酰胺二甲基乙缩醛（DMADMA）转化为烯胺4a – m，然后进行处理用乙酸铵得到（Z）-3-氨基-1-（取代的）丁-2-烯-1-酮5a – m。这些与DMADMA微波辐射下在130℃的密闭容器中进行处理，经由中间体，得到7 - 9最终产物10A -米。N 2，N 2，N 4，N 4-四甲基-6-（取代的）吡啶-2,4-二胺16a – j由一锅法合成，由相应的羧酰胺11a – j通过过量的二甲酰胺处理而制得。 DMADMA在密闭容器中在微波辐射下通过中间体12a – j至15a给出– j最终产品16a – j。烯胺酮5c，5g，5i，5j和5m以及2,4,6-三取代吡啶16a，16b，16g，16i和16j的X射线单晶衍射研究与预期结构一致。
• Reactivity of<i>p</i>-phenyl substituted β-enamino compounds using k-10/ultrasound. I. synthesis of pyrazoles and pyrazolinones
  作者：Claudete J. Valduga、Hugo S. Braibante、Mara E. F. Braibante

  DOI：10.1002/jhet.5570350136

  日期：1998.1

  The reactivity of the β-enamino ketones, 3-amino-1-(p-phenyl-substituted)-2-buten-1-ones 1a-d and β-enamino esters. Ethyl-3-amino-3-(p-phenyl-substituted)-2-propenoates 5a-d were evaluated by systematic studies of the reactions with hydrazine and methylhydrazine by reactions with solid support K-10/ultrasound and homogeneous media (reflux in ethanol or dichloromethane) yielding pyrazole rings 2a-d

  β-烯氨基酮，3-氨基-1-（对苯基取代的）-2-丁烯-1-酮1a-d和β-烯氨基酯的反应性。通过系统研究固体与K-10 /超声波和均质介质（回流）反应，与肼和甲基肼反应，评估了3-氨基-3-（对苯基取代的）-2-丙酸乙酯5a-d。乙醇或二氯甲烷），得到吡唑环2a-d，N-甲基吡唑3a-d，4a-d和N-甲基吡唑啉酮6a-c和7a-c。环化的区域化学显示出所用反应条件以及芳环中的取代基的依赖性。
• Reactivity of<i>p</i>-phenyl substituted β-enamino compounds using K-10/ultrasound.<b>I</b>. Synthesis of pyrazoles and pyrazolinones
  作者：Claudete J. Valduga、Hugo S. Braibante、Mara E. F. Braibante

  DOI：10.1002/jhet.5570340513

  日期：1997.9

  The reactivity of the β-enamino ketones, 3-amino-1-(p-phenyl-substituted)-2-buten-1-ones 1a-d and β-enamino esters, ethyl 3-amino-3-(p-phenyl-substituted)-2-propenoates 5a-d was systematically studied when allowed to react with hydrazine and methylhydrazine under solid support K-10/ultrasound conditions and in homogeneous media (reflux in ethanol or dichloromethane). The products were pyrazoles 2a-d

  β-烯氨基酮，3-氨基-1-（对苯基取代）-2-丁烯-1-酮1a-d和β-烯氨基酯，乙基3-氨基-3-（对苯基）的反应性当在固体载体K -10 /超声条件下和在均相介质（在乙醇或二氯甲烷中回流）下与肼和甲基肼反应时，系统地研究了-取代）-2-丙酸酯5a-d。产物为吡唑2a-d，N-甲基吡唑3a-d，4a-d和N-甲基吡唑啉酮6a-c和7a-c。环化反应的区域化学表明取决于所采用的反应条件以及芳环中的取代基。
• 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。