3-bromo-1-(4-methoxy-benzyl)-4-methyl-6-phenyl-5,6-dihydro-pyridin-2-one | 727425-45-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-1-(4-methoxy-benzyl)-4-methyl-6-phenyl-5,6-dihydro-pyridin-2-one
• 英文别名: 5-Bromo-1-[(4-methoxyphenyl)methyl]-4-methyl-2-phenyl-2,3-dihydropyridin-6-one；5-bromo-1-[(4-methoxyphenyl)methyl]-4-methyl-2-phenyl-2,3-dihydropyridin-6-one
• CAS: 727425-45-8
• 化学式: C₂₀H₂₀BrNO₂
• 分子量: 386.288
• InChiKey: OLGFXHKIRCYJDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(4-methoxy-benzyl)-4-methyl-6-phenyl-5,6-dihydro-pyridin-2-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以70%的产率得到3-bromo-4-methyl-6-phenyl-5,6-dihydro-pyridin-2-one
  参考文献：
  名称：

  Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition

  摘要：

  An approach to 3-bromo-4-alkyl-6-aryl-5,6-dihydropyridin-2-ones and 3 -bromo-5-ethyl-6-aryl-5,6-dihydropyridin-2-ones starting from beta,gamma-unsaturated alpha-bromoketenes and imines is reported. The presence of a bromine atom on the double bond allows performing aziridination or bromine displacement with an amine. The reaction gave fused bicyclic N-allyl-aziridines or 3-amino-substituted 5,6-dihydropyridin-2-ones, depending on the substituents on the six-membered ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.04.021
• 作为产物：
  描述：

  2-溴-3-甲基-2-丁烯酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 3-bromo-1-(4-methoxy-benzyl)-4-methyl-6-phenyl-5,6-dihydro-pyridin-2-one
  参考文献：
  名称：

  Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition

  摘要：

  An approach to 3-bromo-4-alkyl-6-aryl-5,6-dihydropyridin-2-ones and 3 -bromo-5-ethyl-6-aryl-5,6-dihydropyridin-2-ones starting from beta,gamma-unsaturated alpha-bromoketenes and imines is reported. The presence of a bromine atom on the double bond allows performing aziridination or bromine displacement with an amine. The reaction gave fused bicyclic N-allyl-aziridines or 3-amino-substituted 5,6-dihydropyridin-2-ones, depending on the substituents on the six-membered ring. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2004.04.021

文献信息

• The Cycloaddition Reaction Between α-Bromo Vinylketenes and Imines: A Combined Experimental and Theoretical Study
  作者：Fides Benfatti、Andrea Bottoni、Giuliana Cardillo、Serena Fabbroni、Luca Gentilucci、Marco Stenta、Alessandra Tolomelli

  DOI：10.1002/adsc.200800348

  日期：2008.10.6

  The unusual behaviour of α-bromo vinylketenes in the cycloaddition reactions with imines is described. This class of vinylketenes behaves as dienophiles in [2+2] reactions, but also displays an unusual diene reactivity in [4+2] reactions. Interestingly, the reactivity of α-bromo vinylketenes can be modulated via a fine tuning of the substituents. For instance, a methyl group in the β-position completely

  描述了α-溴乙烯酮在与亚胺的环加成反应中的异常行为。这类乙烯基乙烯酮在[2 + 2]反应中表现为亲二烯体，但在[4 + 2]反应中也表现出不同寻常的二烯反应性。有趣的是，可以通过对取代基的微调来调节α-溴乙烯基烯酮的反应性。例如，β位置的甲基完全抑制[2 + 2]反应，几乎只遵循[4 + 2]途径。受阻更大的酮亚胺（而不是简单的亚胺）足以再次激活[2 + 2]机制。我们进行了DFT理论研究，以合理化这些实验观察结果。我们已经考虑了两种途径的[2 + 2]反应涉及亚胺，即，内切和exo途径。对于α-溴乙烯基烯酮，前者是有利的，而对于未取代的乙烯基烯酮，后者是优选的。由于仅当乙烯酮的s - Z-构型显着增加时[4 + 2]环加成才可能，因此该底物中溴取代基的存在对于确定[2 + 2]或[4 + 2]机理至关重要。对于未取代的vinylketenes，连接所述屏障中sE -到SZ -confor
• Practical synthesis of 3-bromo-5,6-dihydropyridin-2-ones via β,γ-unsaturated α-bromo-ketene/imine cycloaddition
  作者：Giuliana Cardillo、Serena Fabbroni、Luca Gentilucci、Rossana Perciaccante、Fabio Piccinelli、Alessandra Tolomelli

  DOI：10.1016/j.tet.2004.04.021

  日期：2004.5

  An approach to 3-bromo-4-alkyl-6-aryl-5,6-dihydropyridin-2-ones and 3 -bromo-5-ethyl-6-aryl-5,6-dihydropyridin-2-ones starting from beta,gamma-unsaturated alpha-bromoketenes and imines is reported. The presence of a bromine atom on the double bond allows performing aziridination or bromine displacement with an amine. The reaction gave fused bicyclic N-allyl-aziridines or 3-amino-substituted 5,6-dihydropyridin-2-ones, depending on the substituents on the six-membered ring. (C) 2004 Published by Elsevier Ltd.