3-acetyl-1,6-dimethyl-1,2,3,4-tetrahydropyridine-2,4-dione | 24681-61-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-1,6-dimethyl-1,2,3,4-tetrahydropyridine-2,4-dione
• 英文别名: 1-Methyl-3-acetyl-6-methyl-2,4-pyridinedione；2,4(1H,3H)-Pyridinedione, 3-acetyl-1,6-dimethyl-；3-acetyl-1,6-dimethylpyridine-2,4-dione
• CAS: 24681-61-6
• 化学式: C₉H₁₁NO₃
• 分子量: 181.191
• InChiKey: ZCNHVSLWGGPSJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-1,6-dimethyl-1,2,3,4-tetrahydropyridine-2,4-dione 在 哌啶 、 甲酸 、 四甲基胍 作用下， 以 甲醇 、 苯 为溶剂， 生成 (E,Z)-3-[4-(benzo[d][1,3]dioxol-5-yl)pyrrolidin-2-ylidene]-1,6-dimethylpyridine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of (4-arylpyrrolidin-2-ylidene) derivatives of cyclic β-dicarbonyl compounds from cinnamoyl precursors

  摘要：

  1,4-Conjugate Michael addition of nitromethane to the enone fragment of cinnamoyl derivatives of carbo- and heterocyclic beta-dicarbonyl compounds provided the corresponding nitromethyl derivatives. The chemoselective reduction of the nitro group in the latter afforded 4-arylpyrrolidin-2-ylidene derivatives of beta-dicarbonyl compounds in high yield. The reaction products with the heterocyclic beta-dicarbonyl fragment are formed as equilibrium mixture of E- and Z-rotamers in which the E-rotamer predominates.

  DOI：

  10.1134/s1070428014110116
• 作为产物：
  描述：

  1,6-二甲基-2-氧代-1,2-二氢-4-吡啶基乙酸酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以83%的产率得到3-acetyl-1,6-dimethyl-1,2,3,4-tetrahydropyridine-2,4-dione
  参考文献：
  名称：

  3-acyl-1,2,3,4-tetrahydropyridine-2,4-diones: Synthesis and chemical properties

  摘要：

  在吡啶或三乙胺存在下，N-取代的 6-甲基-1,2,3,4-四氢吡啶-2,4-二酮与脂肪族羧酸氯化物反应，生成相应的 4-O-酰基衍生物，在 2 等量三乙胺和 2-羟基-2-甲基丙腈催化下，酰基发生 O,C-迁移。由此形成的 3-酰基-6-甲基-1,2,3,4-四氢吡啶-2,4-二酮与脂肪族和芳香族胺反应，在侧酰基上得到相应的烯酰胺衍生物。将 3-酰基-1,2,3,4-四氢吡啶-2,4-二酮与硫酸二甲酯进行烷基化，然后用胺处理，可得到 C4 =O 基团的烯酰胺衍生物。

  DOI：

  10.1134/s1070428008030196

文献信息

• 3-acyl-1,2,3,4-tetrahydropyridine-2,4-diones: Synthesis and chemical properties
  作者：D. B. Rubinov、T. A. Zheldakova、I. L. Rubinova、A. V. Baranovskii

  DOI：10.1134/s1070428008030196

  日期：2008.3

  N-Substituted 6-methyl-1,2,3,4-tetrahydropyridine-2,4-diones reacted with aliphatic carboxylic acid chlorides in the presence of pyridine or triethylamine to give the corresponding 4-O-acyl derivatives which underwent O,C-migration of the acyl group by the action of 2 equiv of triethylamine and a catalytic amount of 2-hydroxy-2-methylpropanenitrile. Reactions of 3-acyl-6-methyl-1,2,3,4-tetrahydropyridine-2,4-diones thus formed with aliphatic and aromatic amines gave the corresponding enamino derivatives at the side acyl group. Enamino derivatives at the C4 =O group were obtained by transformation of 3-acyl-1,2,3,4-tetrahydropyridine-2,4-diones into 3-acyl-4-methoxy-6-methyl-1,2-dihydropyridin-2-ones via alkylation with dimethyl sulfate and subsequent treatment with amines.

  在吡啶或三乙胺存在下，N-取代的 6-甲基-1,2,3,4-四氢吡啶-2,4-二酮与脂肪族羧酸氯化物反应，生成相应的 4-O-酰基衍生物，在 2 等量三乙胺和 2-羟基-2-甲基丙腈催化下，酰基发生 O,C-迁移。由此形成的 3-酰基-6-甲基-1,2,3,4-四氢吡啶-2,4-二酮与脂肪族和芳香族胺反应，在侧酰基上得到相应的烯酰胺衍生物。将 3-酰基-1,2,3,4-四氢吡啶-2,4-二酮与硫酸二甲酯进行烷基化，然后用胺处理，可得到 C4 =O 基团的烯酰胺衍生物。
• Synthesis of (4-arylpyrrolidin-2-ylidene) derivatives of cyclic β-dicarbonyl compounds from cinnamoyl precursors
  作者：F. S. Pashkovskii、Yu. S. Dontsu、D. B. Rubinov、F. A. Lakhvich、V. F. Traven’、A. M. Borunov

  DOI：10.1134/s1070428014110116

  日期：2014.11

  1,4-Conjugate Michael addition of nitromethane to the enone fragment of cinnamoyl derivatives of carbo- and heterocyclic beta-dicarbonyl compounds provided the corresponding nitromethyl derivatives. The chemoselective reduction of the nitro group in the latter afforded 4-arylpyrrolidin-2-ylidene derivatives of beta-dicarbonyl compounds in high yield. The reaction products with the heterocyclic beta-dicarbonyl fragment are formed as equilibrium mixture of E- and Z-rotamers in which the E-rotamer predominates.