5-乙基-1-异丙基-3,4-二氢-2(1H)-吡啶酮 | 143818-35-3

• 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
• 中文名称: 5-乙基-1-异丙基-3,4-二氢-2(1H)-吡啶酮
• 中文别名: 1H-吡唑并[3,4-d]噻唑-3,5(2H,6H)-二酮
• 英文名称: 5-ethyl-1-isopropyl-3,4-dihydro-1H-pyridin-2-one
• 英文别名: 5-Ethyl-1-propan-2-yl-3,4-dihydropyridin-2-one
• CAS: 143818-35-3
• 化学式: C₁₀H₁₇NO
• 分子量: 167.251
• InChiKey: SKHLCUPOJODRFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-but-1-enyl-N-propan-2-ylprop-2-enamide 800.0 ℃ 、0.2 Pa 条件下， 以55%的产率得到5-乙基-1-异丙基-3,4-二氢-2(1H)-吡啶酮
  参考文献：
  名称：

  SUCCESSFUL THERMAL REARRANGEMENTS OF ACRYLENAMIDES TO GIVE TETRAHYDRO-2-PYRIDONES UNDER FVT CONDITIONS

  摘要：

  Enamides of alpha,beta-unsaturated acids are theoretically capable of electrocyclisation to give tetrahydro-2-pyridones. The only successful method reported for this conversion involved photochemical activation. We would like to present new and effective method for this transformation using flash vacuum thermolysis.

  DOI：

  10.1081/scc-120002697

文献信息

• Formation of 1,2,3,4-tetrahydro-2-pyridones by aza-annulation of imines with acrylate derivatives
  作者：K. Paulvannan、John R. Stille

  DOI：10.1021/jo00046a011

  日期：1992.9

  The aza-annulation of imines with activated acrylate derivatives was studied as a means of preparing the corresponding 1,2,3,4-tetrahydro-2-pyridones. Through the use of reagents known to facilitate the formation of amide bonds from carboxylic acids, several methods of activating the acrylate species were compared. The acrylate derivatives studied were acryloyl chloride and acrylic anhydride as well as acrylic acid activated by reaction with EtO2CCl, (PhO)2P(O)N3, or MCPI. Optimum annulation was obtained with imines derived from cyclohexanone to produce octahydro-2-quinolone products. The N-isobutylimine prepared from cyclopentanone also produced selective ring annulation to efficiently produce the corresponding bicyclic product, but the reaction with the imine of n-butanal produced lower yields of cyclic product. Ring formation was relatively unaffected by substituents at the a-position of the acrylate derivative, demonstrated by the use of methacrylate, but beta-substituents hindered the annulation process and, in turn, increased the amounts of byproduct resulting from only N-acylation of the imine. Increasing the steric bulk of the imine alkyl substituent produced the opposite effect; the relative amount of N-acylation compared to complete aza-annulation was diminished as the size of the substituent was increased. Mechanistic features of the reaction are discussed in terms of product distribution and competition experiments.