3,5-diacetyl-4-(4-methoxyphenyl)-1,4-dihydropyridine | 212623-27-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,5-diacetyl-4-(4-methoxyphenyl)-1,4-dihydropyridine
• 英文别名: 1-[5-Acetyl-4-(4-methoxyphenyl)-1,4-dihydropyridin-3-yl]ethanone
• CAS: 212623-27-3
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: CKMCTSAQLGRFPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-diacetyl-4-(4-methoxyphenyl)-1,4-dihydropyridine 在 吡啶 、 高氯酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 50.0h， 生成 Acetic acid (4R,4aS,9aS)-1,3,4a-triacetyl-4-(4-methoxy-phenyl)-1,4,4a,9a-tetrahydro-benzo[4,5]furo[2,3-b]pyridin-6-yl ester
  参考文献：
  名称：

  Novel Synthesis of Polyfunctionalized 1,4,4a,9a-Tetrahydro-1-aza-9-oxafluorenes by Unexpected Cycloaddition of 4-(4-Methoxyphenyl)-1,4-dihydropyridines and p-Benzoquinone

  摘要：

  A surprising acid-catalysed cycloaddition reaction occurs between 3,5-diacetyl-4-(4-methoxyphenyl)-1,4-dihydropyridine (4) and p-benzoquinone in dioxane/HClO4 (5%) yielding novel polyfunctionalized 1,4,4a,9a-tetrahydro-1-aza-9-oxafluorenes (9) as exclusive products. On the other hand the corresponding 4-unsubstituted 1,4-dihydropyridine (1) is oxidized by p-benzoquinone. Novel structures are characterized by standard spectroscopy and, furthermore, confirmed by acetylation. The different reactivity of the 4-substituted and 4-unsubstituted derivatives is dicussed on the basis of semiempirical MNDO calculations and redox potentials.

  DOI：

  10.3987/com-98-8189
• 作为产物：
  描述：

  3-oxo-butyraldehyde; sodium enolate 、 4-甲氧基苯甲醛 在 ammonium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以32%的产率得到3,5-diacetyl-4-(4-methoxyphenyl)-1,4-dihydropyridine
  参考文献：
  名称：

  新型功能化的1,4,4a，9a-四氢-1-氮杂-9-氧杂芴类化合物通过环加成4-（4-甲氧基苯基）-1,4-二氢吡啶和对-苯醌

  摘要：

  DOI：

  10.1002/jhet.5570350310

文献信息

• Novel Synthesis of Polyfunctionalized 1,4,4a,9a-Tetrahydro-1-aza-9-oxafluorenes by Unexpected Cycloaddition of 4-(4-Methoxyphenyl)-1,4-dihydropyridines and p-Benzoquinone
  作者：Andreas Hilgeroth、Krystina Kuna、Uwe Kuckländer

  DOI：10.3987/com-98-8189

  日期：——

  A surprising acid-catalysed cycloaddition reaction occurs between 3,5-diacetyl-4-(4-methoxyphenyl)-1,4-dihydropyridine (4) and p-benzoquinone in dioxane/HClO4 (5%) yielding novel polyfunctionalized 1,4,4a,9a-tetrahydro-1-aza-9-oxafluorenes (9) as exclusive products. On the other hand the corresponding 4-unsubstituted 1,4-dihydropyridine (1) is oxidized by p-benzoquinone. Novel structures are characterized by standard spectroscopy and, furthermore, confirmed by acetylation. The different reactivity of the 4-substituted and 4-unsubstituted derivatives is dicussed on the basis of semiempirical MNDO calculations and redox potentials.
• Novel functionalized 1,4,4a,9a-tetrahydro-1-aza-9-oxafluorenes by cycloaddition of 4-(4-methoxyphenyl)-1,4-dihydropyridines and<i>p</i>-benzoquinone
  作者：Andreas Hilgeroth、Krystina Kuna、Uwe Kuckländer

  DOI：10.1002/jhet.5570350310

  日期：1998.5