diethyl 4-[5-bromo-2-[(E)-3-ethoxy-3-oxoprop-1-enoxy]phenyl]-1-(4-methylphenyl)-4H-pyridine-3,5-dicarboxylate | 954374-96-0

• 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: diethyl 4-[5-bromo-2-[(E)-3-ethoxy-3-oxoprop-1-enoxy]phenyl]-1-(4-methylphenyl)-4H-pyridine-3,5-dicarboxylate
• CAS: 954374-96-0
• 化学式: C₂₉H₃₀BrNO₇
• 分子量: 584.464
• InChiKey: YMMQBEYMFFAPRW-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  91.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  diethyl 4-[5-bromo-2-[(E)-3-ethoxy-3-oxoprop-1-enoxy]phenyl]-1-(4-methylphenyl)-4H-pyridine-3,5-dicarboxylate 在 四氢吡咯 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到diethyl 4-(5-bromo-2-hydroxyphenyl)-1-(4-methylphenyl)-4H-pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Domino Reaction of 3-(2-Formylphenoxy)propenoates and Amines:  A Novel Synthesis of 1,4-Dihydropyridines from Salicaldehydes, Ethyl Propiolate, and Amines

  摘要：

  [GRAPHICS]A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines has been developed. Salicaldehydes were treated with ethyl propiolate in the presence of N-methylmorpholine to give ethyl 3-(2-formylphenoxy)propenoates. Three equivalents of ethyl 3-(2-formylphenoxy)propenoates reacted with 1 equiv of amines under trifluoroacetic acid (TFA) catalyst to furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields, recovering the starting material salicaldehydes. A possible mechanism for the domino process was proposed. Furthermore, the products can be easily derived via further transformations and three of them exhibited strong fluorescence (Phi(f) = 0.36-0.63).

  DOI：

  10.1021/jo7013593
• 作为产物：
  描述：

  丙炔酸乙酯 在 N-甲基吗啉 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 diethyl 4-[5-bromo-2-[(E)-3-ethoxy-3-oxoprop-1-enoxy]phenyl]-1-(4-methylphenyl)-4H-pyridine-3,5-dicarboxylate
  参考文献：
  名称：

  Domino Reaction of 3-(2-Formylphenoxy)propenoates and Amines:  A Novel Synthesis of 1,4-Dihydropyridines from Salicaldehydes, Ethyl Propiolate, and Amines

  摘要：

  [GRAPHICS]A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines has been developed. Salicaldehydes were treated with ethyl propiolate in the presence of N-methylmorpholine to give ethyl 3-(2-formylphenoxy)propenoates. Three equivalents of ethyl 3-(2-formylphenoxy)propenoates reacted with 1 equiv of amines under trifluoroacetic acid (TFA) catalyst to furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields, recovering the starting material salicaldehydes. A possible mechanism for the domino process was proposed. Furthermore, the products can be easily derived via further transformations and three of them exhibited strong fluorescence (Phi(f) = 0.36-0.63).

  DOI：

  10.1021/jo7013593

文献信息

• Domino Reaction of 3-(2-Formylphenoxy)propenoates and Amines:  A Novel Synthesis of 1,4-Dihydropyridines from Salicaldehydes, Ethyl Propiolate, and Amines
  作者：Sun-Liang Cui、Jun Wang、Xu-Feng Lin、Yan-Guang Wang

  DOI：10.1021/jo7013593

  日期：2007.9.1

  [GRAPHICS]A novel synthesis of Hantzsch-type N-substituted 1,4-dihydropyridines from salicaldehydes, ethyl propiolate, and amines has been developed. Salicaldehydes were treated with ethyl propiolate in the presence of N-methylmorpholine to give ethyl 3-(2-formylphenoxy)propenoates. Three equivalents of ethyl 3-(2-formylphenoxy)propenoates reacted with 1 equiv of amines under trifluoroacetic acid (TFA) catalyst to furnish the corresponding N-substituted 1,4-dihydropyridines in good to excellent yields, recovering the starting material salicaldehydes. A possible mechanism for the domino process was proposed. Furthermore, the products can be easily derived via further transformations and three of them exhibited strong fluorescence (Phi(f) = 0.36-0.63).