1-methyl-2,3,4-triphenyl-2H-pyrrol-5-one | 67302-58-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1-methyl-2,3,4-triphenyl-2H-pyrrol-5-one
• CAS: 67302-58-3
• 化学式: C₂₃H₁₉NO
• 分子量: 325.41
• InChiKey: XTGFVHQJXWZTLE-UHFFFAOYSA-N

物化性质

• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  1-methyl-2,3,4-triphenyl-2H-pyrrol-5-one 在 三氟甲磺酸 作用下， 以100%的产率得到2-methyl-3-phenyl-2,3-dihydro-dibenzo[e,g]isoindol-1-one
  参考文献：
  名称：

  Aza-Nazarov Reaction and the Role of Superelectrophiles

  摘要：

  [GRAPHICS]The superacid-catalyzed reactions of N-acyliminium ion salts have been studied. The new conversions are remarkably similar to the Nazarov reaction and dicationic superelectrophilic species are thought to be involved. Experimental studies show that the cyclizations may be used to prepare varied heterocyclic products, while theoretical studies show that formation of the superelectrophiles can lead to very favorable reaction energetics.

  DOI：

  10.1021/ol0711570
• 作为产物：
  描述：

  苯亚甲基甲胺 在 三氟甲磺酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.0h， 生成 1-methyl-2,3,4-triphenyl-2H-pyrrol-5-one
  参考文献：
  名称：

  Aza-Nazarov Reaction and the Role of Superelectrophiles

  摘要：

  [GRAPHICS]The superacid-catalyzed reactions of N-acyliminium ion salts have been studied. The new conversions are remarkably similar to the Nazarov reaction and dicationic superelectrophilic species are thought to be involved. Experimental studies show that the cyclizations may be used to prepare varied heterocyclic products, while theoretical studies show that formation of the superelectrophiles can lead to very favorable reaction energetics.

  DOI：

  10.1021/ol0711570

文献信息

• Reaction of aminocarbene complexes of chromium with alkynes 9.
  作者：Henri Rudler、Andrée Parlier、Michèle Rudler、Jacqueline Vaissermann

  DOI：10.1016/s0022-328x(98)00672-x

  日期：1998.9

  to give pyrrolinones as the result of the insertions of the alkyne, of CO and the migration of an alkyl group from nitrogen to a carbon atom in α or γ with respect to the nitrogen atom. The mechanism of this new reaction has been thoroughly investigated: a nitrogen ylid originating from the interaction of the nitrogen atom of the starting aminocarbene complex with the central carbon of the ketene formed

  铬的络合物Aminocarbene具有通式结构（CO）5 CrC（R）NR 1 - [R 2与二苯基乙炔反应，得到pyrrolinones作为炔的插入，CO和一个烷基的选自氮到迁移的结果在碳原子α或γ相对于氮原子上。已对该新反应的机理进行了深入研究：源自起始氨基卡宾配合物的氮原子与炔烃和CO插入氨基卡宾配合物形成的乙烯酮中心碳相互作用的氮基是这些反应中的关键中间体。这种ylid配合物，其结构可以确定为25，导致在热解时观察到的吡咯烷酮。基于环丙基羰基取代的氨基卡宾配合物45a，b的反应，已经放弃了涉及自由基的机理：如吡咯烷酮46b的X射线结构所示，在其迁移时未观察到环丙基羰基的重排。还消除了涉及离子对或金属参与的机理。为此，已经建立了两个配合物51和52的X射线结构，其中金属不与迁移基团的苯环键合。最后，在氢中，从氮到五元杂环碳的烷基一致的（1,5）σ迁移。25个观察结果最佳。金属的作用
• Reaction of aminocarbene complexes of chromium with alkynes IV. New transformations of the nitrogen ylide complexes derived therefrom
  作者：Cecile Bouancheau、Michele Rudler、Evelyne Chelain、Henri Rudler、Jacqueline Vaissermann、Jean-Claude Daran

  DOI：10.1016/0022-328x(95)05447-w

  日期：1995.6

  obtained from aminocarbene complexes of chromium and diphenylacetylene failed. With dioxygen under UV irradiation, insertion of an oxygen atom into the NC(O) bond gave aminolactones 8 instead. With sulfur a series of aminofuran complexes 9 were obtained. Olefins such as cyclopentadiene and cyclooctene did not cycloadd to these ylide complexes. Whereas no reaction was observed with cylooctene, with cyclopentadiene

  试图从由铬和二苯基乙炔的氨基卡宾配合物获得的一系列N- ylide配合物中除去Cr（CO）3基团的尝试失败了。在紫外线照射下，用双氧将氧原子插入NC（O）键可得到氨基内酯8。用硫获得了一系列氨基呋喃配合物9。烯烃如环戊二烯和环辛烯没有环加到这些叶立德络合物中。而没有反应物用cylooctene观察到，与环戊二烯的总质子化脱甲基-脱金属反应ñ -二甲基内鎓盐络合物图4a和4b中的pyrrolinones 10A和10B发生。用（ArPS 2）2观察到相同的质子化-脱烷基化反应。因此4a，4b和4d导致10a，10b和10d。通过对衍生自哌啶的N-基化物4f和4g进行类似的反应来确定离去烷基的命运，得到内酯硫醇11f和11g。氨基呋喃配合物9b的结构通过X射线晶体学明确地确定。N的结构之间的关系-叶立德配合物和反应产物进行了讨论。
• Aza-Nazarov Reaction and the Role of Superelectrophiles
  作者：Douglas A. Klumpp、Yiliang Zhang、Matthew J. O'Connor、Pierre M. Esteves、Leonardo S. de Almeida

  DOI：10.1021/ol0711570

  日期：2007.8.1

  [GRAPHICS]The superacid-catalyzed reactions of N-acyliminium ion salts have been studied. The new conversions are remarkably similar to the Nazarov reaction and dicationic superelectrophilic species are thought to be involved. Experimental studies show that the cyclizations may be used to prepare varied heterocyclic products, while theoretical studies show that formation of the superelectrophiles can lead to very favorable reaction energetics.