3-methyl-4-phenyl-2H-cyclopentapyridin-2-one | 83021-67-4

• 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
• 英文名称: 3-methyl-4-phenyl-2H-cyclopentapyridin-2-one
• 英文别名: 3-methyl-4-phenyl-1,5,6,7-tetrahydrocyclopenta[b]pyridin-2-one
• CAS: 83021-67-4
• 化学式: C₁₅H₁₅NO
• 分子量: 225.29
• InChiKey: SUQHARKYZSIPLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-methyl-4-phenyl-2H-cyclopentapyridin-2-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 rac-(5R,9bR)-5,10-dimethyl-4-phenyl-1,2,3,5-tetrahydro-9b,5-(epiminomethano)cyclopenta[a]naphthalen-11-one
  参考文献：
  名称：

  DIELS–ALDER ADDUCTS FROM N-UNSUBSTITUTED TAUTOMERIC 2(1H)-PYRIDONE-2-HYDROXYPYRIDINES; 5,6-BENZO-2-AZABARRELENONES AND 5,6-BENZO-2-AZABARRELENES

  摘要：

  对几种无取代的互变异构体2(1H)-吡啶酮-2-羟基吡啶与苯炔的Diels–Alder反应进行了研究，发现它们生成了5,6-苯并-2-氮杂巴伦酮，随后这些化合物被转化为迄今未知的5,6-苯并-2-氮杂巴伦烯。

  DOI：

  10.1246/cl.1982.475

文献信息

• Reactions of 1-unsubstituted tautomeric 2-pyridones with benzyne.
  作者：MASAYUKI KUZUYA、AKIHIRO NOGUCHI、SHOJI KAMIYA、TAKACHIYO OKUDA

  DOI：10.1248/cpb.33.2313

  日期：——

  The reactions of 1-unsubstituted 2-pyridones with benzyne afforded the Diels-Alder adduct, 5, 6-benzo-2-azabarrelen-3 (2H)-ones, together with a large amount of the Michael-type adduct, 2-phenoxypyridines.

  1-未取代的2-吡啶酮与苯炔的反应生成了Diels-Alder加成产物5, 6-苯并-2-氮杂巴雷ланы-3 (2H)-酮，同时生成了大量的迈克尔型加成产物2-苯氧基吡啶。
• The Structure–Reactivity–Chemoselectivity Relationship on the Reactions of 1-Unsubstituted Tautomeric 2-Pyridones with Benzyne
  作者：Masayuki Kuzuya、Akihiro Noguchi、Ei-ichi Mano、Takachiyo Okuda

  DOI：10.1246/bcsj.58.1149

  日期：1985.4

  The reactions of 2-pyridones with benzyne were investigated in order to gain some insight into the structure–reactivity–chemoselectivity relationship involved in the tautomeric systems. All reactions examined have resulted in the formation of Diels-Alder and Michael-type adducts. It has been shown that the Diels-Alder reactivities were well correlated with the HOMO energy levels of the 2-pyridone form and the yields of the Michael-type adduct were closely associated with the tautomeric equilibria. In summary, the chemoselectivities of 2-pyridones in the reaction with benzyne were largely affected by the tautomeric properties.

  对2-吡啶酮与苯炔的反应进行了研究，以获取有关该互变异构体系中结构-反应性-化学选择性关系的深入见解。所有检查的反应都导致了狄尔斯-阿尔德和迈克尔型加成物的形成。研究表明，狄尔斯-阿尔德的反应性与2-吡啶酮形式的最高占据分子轨道（HOMO）能级之间有良好的相关性，而迈克尔型加成物的产率与互变平衡密切相关。总之，2-吡啶酮与苯炔反应中的化学选择性受到互变特性的很大影响。
• KUZUYA, MASAYUKI;MANO, EI-ICHI;ADACHI, MICHIHIRO;NOGUCHI, AKIHIRO;OKUDA, +, CHEM. LETT., 1982, N 4, 475-478
  作者：KUZUYA, MASAYUKI、MANO, EI-ICHI、ADACHI, MICHIHIRO、NOGUCHI, AKIHIRO、OKUDA, +

  DOI：——

  日期：——
• KUZUYA, MASAYUKI;NOGUCHI, AKIHIRO;KAMIYA, SHOJI;OKUDA, TAKACHIYO, CHEM. AND PHARM. BULL., 1985, 33, N 6, 2313-2322
  作者：KUZUYA, MASAYUKI、NOGUCHI, AKIHIRO、KAMIYA, SHOJI、OKUDA, TAKACHIYO

  DOI：——

  日期：——
• DIELS–ALDER ADDUCTS FROM N-UNSUBSTITUTED TAUTOMERIC 2(1<i>H</i>)-PYRIDONE-2-HYDROXYPYRIDINES; 5,6-BENZO-2-AZABARRELENONES AND 5,6-BENZO-2-AZABARRELENES
  作者：Masayuki Kuzuya、Ei-ichi Mano、Michihiro Adachi、Akihiro Noguchi、Takachiyo Okuda

  DOI：10.1246/cl.1982.475

  日期：1982.4.5

  Diels–Alder reactions of several N-unsubstituted tautomeric 2(1H)-pyridone-2-hydroxypyridines with benzyne were examined and found to afford 5,6-benzo-2-azabarrelenones, which were converted to hitherto unknown 5,6-benzo-2-azabarrelenes.

  对几种无取代的互变异构体2(1H)-吡啶酮-2-羟基吡啶与苯炔的Diels–Alder反应进行了研究，发现它们生成了5,6-苯并-2-氮杂巴伦酮，随后这些化合物被转化为迄今未知的5,6-苯并-2-氮杂巴伦烯。