(E)-3-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-but-2-enoic acid methyl ester | 244238-88-8

• 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: (E)-3-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-but-2-enoic acid methyl ester
• CAS: 244238-88-8
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: ANWXCSYZCKNPSL-AVPQAVFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.09
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  81.8
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  反式-3-(1-吡咯烷酮)丙烯酸乙酯 、 (E)-3-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-but-2-enoic acid methyl ester 反应 15.0h， 以61%的产率得到3-O-ethyl 5-O-methyl 6-methyl-2-(4-nitrophenyl)-1,2-dihydropyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Reaction of N-Vinylic Phosphazenes Derived from β-Amino Acids with Aldehydes. Azadiene-Mediated Synthesis of Dihydropyridines, Pyridines, and Polycyclic Nitrogen Derivatives

  摘要：

  Enamino phosphonium salts 2 are obtained by 1,2-addition of hydrogen chloride to N-vinylic phosphazenes 1 derived from triphenylphosphine. Aza-Wittig reaction of phosphazenes 1 derived from triphenylphosphine and 6 derived from diphenylmethylphosphine with aldehydes 3 leads to the formation of 2-azadienes 7. Reaction of azadienes 7 with enamines affords dihydropyridines 9 and 11, pyridines 12, and bicyclic nitrogen heterocycles 15-18 in a regioselective fashion, while heterodiene 20 reacts in the same way with pyrrolidinocyclohexanone giving 1-azaphenanthrene compound 21. Reaction of enamino phosphonium salts 2 with aldehydes 3 gives symmetrical dihydropyridines 5.

  DOI：

  10.1021/jo9902650
• 作为产物：
  描述：

  对硝基苯甲醛 、 methyl (E)-3-(triphenylphosphoranylideneamino)but-2-enoate 反应 3.0h， 以61%的产率得到(E)-3-{[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-amino}-but-2-enoic acid methyl ester
  参考文献：
  名称：

  Reaction of N-Vinylic Phosphazenes Derived from β-Amino Acids with Aldehydes. Azadiene-Mediated Synthesis of Dihydropyridines, Pyridines, and Polycyclic Nitrogen Derivatives

  摘要：

  Enamino phosphonium salts 2 are obtained by 1,2-addition of hydrogen chloride to N-vinylic phosphazenes 1 derived from triphenylphosphine. Aza-Wittig reaction of phosphazenes 1 derived from triphenylphosphine and 6 derived from diphenylmethylphosphine with aldehydes 3 leads to the formation of 2-azadienes 7. Reaction of azadienes 7 with enamines affords dihydropyridines 9 and 11, pyridines 12, and bicyclic nitrogen heterocycles 15-18 in a regioselective fashion, while heterodiene 20 reacts in the same way with pyrrolidinocyclohexanone giving 1-azaphenanthrene compound 21. Reaction of enamino phosphonium salts 2 with aldehydes 3 gives symmetrical dihydropyridines 5.

  DOI：

  10.1021/jo9902650

文献信息

• Cycloaddition Reaction of 2-Azadienes Derived from β-Amino Acids with Electron-Rich and Electron-Deficient Alkenes and Carbonyl Compounds. Synthesis of Pyridine and 1,3-Oxazine Derivatives
  作者：Francisco Palacios、Esther Herrán、Gloria Rubiales、Jose María Ezpeleta

  DOI：10.1021/jo016273+

  日期：2002.4.1

  Functionalized keto-enamines 6 were obtained by nucleophilic addition of enol ethers to the imine moiety of 2-azadienes derived from dehydroaspartic esters 4. Reactions of 2-azadiene 4c containing three electron-withdrawing substituents (CO(2)R) with enol ethers 5 in the presence of lithium perchlorate led to the formation of tetrahydropyridine derivatives 7 in a regio- and stereoselective fashion

  通过将烯醇醚亲核加成于衍生自脱氢天冬氨酸酯4的2-氮杂二烯的亚胺部分，可以得到官能化的酮-烯胺6。含有三个吸电子取代基（CO（2）R）的2-氮杂二烯4c与烯醇醚5的反应在高氯酸锂存在下，以区域和立体选择性方式形成四氢吡啶衍生物7。2H- [1,3]-恶嗪10和吡啶衍生物12和13通过含两个吸电子取代基（4-O（2）NC（6）H（4）的贫电子氮杂二烯4d-g的杂环加成反应获得，CO（2）R）在位置1和4与羰基衍生物（乙二醛酸乙酯9a和酮戊二酸二乙酯9b）和缺电子的烯烃四氰基乙烯11。