Dimethyl 1-(4-methylphenyl)sulfonyl-6-oxopyridine-3,4-dicarboxylate | 1134629-90-5

• 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: Dimethyl 1-(4-methylphenyl)sulfonyl-6-oxopyridine-3,4-dicarboxylate
• 英文别名: dimethyl 1-(4-methylphenyl)sulfonyl-6-oxopyridine-3,4-dicarboxylate
• CAS: 1134629-90-5
• 化学式: C₁₆H₁₅NO₇S
• 分子量: 365.364
• InChiKey: YOFILRHNCBQZPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  115
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Dimethyl 1-(4-methylphenyl)sulfonyl-6-oxopyridine-3,4-dicarboxylate 、 2,3-二甲基-1,3-丁二烯 以 邻二甲苯 为溶剂， 反应 48.0h， 以27%的产率得到
  参考文献：
  名称：

  Diels-Alder Reaction of 2-Pyridones Having an Acyl or a Sulfonyl Group on Nitrogen

  摘要：

  Diels-Alder (DA) reaction of 5-methoxycarbonyl-2-pyridone, which has an electron-withdrawing acyl group at nitrogen, with 1,3-diene afforded 2-quinolone derivatives in modest yields. Further, DA reaction of 5,4-dimethoxycarbonyl-1-sulfonyl-2-pyridone gave 2-quinolone and 1-isoquinolone (1:1). DA reaction of 2-sulfonyl-1-isoquinolone afforded a functionalized phenanthridone. The site-selectivity was well correlated with the corresponding activation energies calculated using an ab initio molecular orbital method.

  DOI：

  10.3987/com-08-s(f)4
• 作为产物：
  描述：

  4,5-dimethoxycarbonyl-2(1H)-pyridone 、 对甲苯磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到Dimethyl 1-(4-methylphenyl)sulfonyl-6-oxopyridine-3,4-dicarboxylate
  参考文献：
  名称：

  Diels-Alder Reaction of 2-Pyridones Having an Acyl or a Sulfonyl Group on Nitrogen

  摘要：

  Diels-Alder (DA) reaction of 5-methoxycarbonyl-2-pyridone, which has an electron-withdrawing acyl group at nitrogen, with 1,3-diene afforded 2-quinolone derivatives in modest yields. Further, DA reaction of 5,4-dimethoxycarbonyl-1-sulfonyl-2-pyridone gave 2-quinolone and 1-isoquinolone (1:1). DA reaction of 2-sulfonyl-1-isoquinolone afforded a functionalized phenanthridone. The site-selectivity was well correlated with the corresponding activation energies calculated using an ab initio molecular orbital method.

  DOI：

  10.3987/com-08-s(f)4

文献信息

• Diels-Alder Reaction of 2-Pyridones Having an Acyl or a Sulfonyl Group on Nitrogen
  作者：Reiko Fujita、Masato Hoshino、Kazuhiro Watanabe、Yosuke Ohtake、Takeshi Sato、Hisao Matsuzaki

  DOI：10.3987/com-08-s(f)4

  日期：——

  Diels-Alder (DA) reaction of 5-methoxycarbonyl-2-pyridone, which has an electron-withdrawing acyl group at nitrogen, with 1,3-diene afforded 2-quinolone derivatives in modest yields. Further, DA reaction of 5,4-dimethoxycarbonyl-1-sulfonyl-2-pyridone gave 2-quinolone and 1-isoquinolone (1:1). DA reaction of 2-sulfonyl-1-isoquinolone afforded a functionalized phenanthridone. The site-selectivity was well correlated with the corresponding activation energies calculated using an ab initio molecular orbital method.