5-acetyl-1,6-dimethyl-1,2,3,4-tetrahydro-2-pyridinone | 13729-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-acetyl-1,6-dimethyl-1,2,3,4-tetrahydro-2-pyridinone
• 英文别名: 1-Methyl-2-oxo-5-acetyl-6-methyl-1,2,3,4-tetrahydro-pyridin；5-acetyl-1,6-dimethyl-3,4-dihydro-1H-pyridin-2-one；5-Acetyl-1,6-dimethyl-3,4-dihydropyridin-2-one
• CAS: 13729-70-9
• 化学式: C₉H₁₃NO₂
• 分子量: 167.208
• InChiKey: KEYSBSYBYVQAHK-UHFFFAOYSA-N

物化性质

• 沸点：
  315.1±41.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-acetyl-1,6-dimethyl-1,2,3,4-tetrahydro-2-pyridinone 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以97%的产率得到5-(1-hydroxyethyl)-1,6-dimethyl-1,2,3,4-tetrahydro-2-pyridinone
  参考文献：
  名称：

  Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the selective reduction of acylated enaminones

  摘要：

  A convenient methodology for the stereoselective preparation of 5-alkyliden-6-aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2-pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3, an accessible starling material obtained by mild and selective reduction of the 5-acyltetrahydro-2-pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2-pyranone 4 was investigated and rationalized. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10333-7
• 作为产物：
  描述：

  (Z)-4-(methylamino)-3-penten-2-one 、 丙烯酰氯 以 四氢呋喃 为溶剂， 生成 5-acetyl-1,6-dimethyl-1,2,3,4-tetrahydro-2-pyridinone
  参考文献：
  名称：

  Stereoselective synthesis of 5-alkyliden-6-aminotetrahydro-2-pyranones through an unexpected isomerization of the hydroxytetrahydro-2-pyridinones obtained by the selective reduction of acylated enaminones

  摘要：

  A convenient methodology for the stereoselective preparation of 5-alkyliden-6-aminotetrahydro-2-pyranone 4 is reported. The synthesis of 2-pyranone 4 occurs through an unknown isomerization mechanism of the hydroxytetrahydro-2-pyridinone 3, an accessible starling material obtained by mild and selective reduction of the 5-acyltetrahydro-2-pyridinone 2. The isomerization mechanism and the stereoselectivity in the synthesis of 2-pyranone 4 was investigated and rationalized. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(97)10333-7

文献信息

• SHABANA R.; SCHEIBYE S.; CLAUSEN K.; OLESEN S. O.; LAWESSON S.-O., NOUV. J. CHIM., 1980, 4, NO 1, 47-51
  作者：SHABANA R.、 SCHEIBYE S.、 CLAUSEN K.、 OLESEN S. O.、 LAWESSON S.-O.

  DOI：——

  日期：——