(R)-(-)-1-(1-phenylethyl)-6-[(E)-styryl]-3,4-dihydro-1H-pyridin-2-one | 592512-39-5

• 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: (R)-(-)-1-(1-phenylethyl)-6-[(E)-styryl]-3,4-dihydro-1H-pyridin-2-one
• 英文别名: 6-[(E)-2-phenylethenyl]-1-[(1R)-1-phenylethyl]-3,4-dihydropyridin-2-one
• CAS: 592512-39-5
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: FNKPQVNFENTBPT-INFVRCAFSA-N

物化性质

• 沸点：
  500.4±40.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-N-isopropyl-N-(1-phenylethyl)acrylamide 、 (R)-(-)-1-(1-phenylethyl)-6-[(E)-styryl]-3,4-dihydro-1H-pyridin-2-one 以 甲苯 为溶剂， 反应 48.0h， 以28%的产率得到(-)-(4aR,6R,7R)-2-oxo-7-phenyl-1-(R)-(1-phenylethyl)-1,2,3,4,4a,5,6,7-octahydroquinoline-6-carboxylic acid (S)-(1-phenylethyl)amide
  参考文献：
  名称：

  Preparation and Cycloaddition Reactions of Enantiopure 2-(N-Acylamino)-1,3-dienes for the Synthesis of Octahydroquinoline Derivatives

  摘要：

  Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions were carried out with a glutarimide-derived vinyl phosphate, bearing a chiral auxiliary on the N atom, to prepare enantiopure 2-(N-acylamino)-1,3-dienes as partners in Diels-Alder reactions. The cycloadditions were performed with various dienophiles under thermal conditions, with or without Lewis acids. With maleimides, the preferential formation of endo cycloadducts was observed, whereas with acrylamides the exo approach prevailed. Furthermore, in the latter case, 6-substitued octahydro-quinolinones were obtained in accordance with the predicted regioselectivity. Since diastereopure compounds were in all cases obtained either by chromatography or by crystallization, and because of the easy access to a variety of boronic acids, to be used in the coupling step, this methodology is useful for the short synthesis of differently substituted, enantiopure octahydroquinolinones amenable to further transformation into decahydroquinolines possessing interesting biological activities.

  DOI：

  10.1021/jo0344687
• 作为产物：
  描述：

  (R)-(+)-1-(1-phenylethyl)piperidine-2,6-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 sodium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (R)-(-)-1-(1-phenylethyl)-6-[(E)-styryl]-3,4-dihydro-1H-pyridin-2-one
  参考文献：
  名称：

  Preparation and Cycloaddition Reactions of Enantiopure 2-(N-Acylamino)-1,3-dienes for the Synthesis of Octahydroquinoline Derivatives

  摘要：

  Stille, Suzuki-Miyaura, and Sonogashira cross-coupling reactions were carried out with a glutarimide-derived vinyl phosphate, bearing a chiral auxiliary on the N atom, to prepare enantiopure 2-(N-acylamino)-1,3-dienes as partners in Diels-Alder reactions. The cycloadditions were performed with various dienophiles under thermal conditions, with or without Lewis acids. With maleimides, the preferential formation of endo cycloadducts was observed, whereas with acrylamides the exo approach prevailed. Furthermore, in the latter case, 6-substitued octahydro-quinolinones were obtained in accordance with the predicted regioselectivity. Since diastereopure compounds were in all cases obtained either by chromatography or by crystallization, and because of the easy access to a variety of boronic acids, to be used in the coupling step, this methodology is useful for the short synthesis of differently substituted, enantiopure octahydroquinolinones amenable to further transformation into decahydroquinolines possessing interesting biological activities.

  DOI：

  10.1021/jo0344687