1,3-Diphenyl-4-benzoyl-azetidinon-(2) | 15088-38-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 1,3-Diphenyl-4-benzoyl-azetidinon-(2)
• 英文别名: 4-benzoyl-1,3-diphenylazetidin-2-one
• CAS: 15088-38-7
• 化学式: C₂₂H₁₇NO₂
• 分子量: 327.382
• InChiKey: ZTEDSAWGUPNMCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  C-benzoyl-N-phenylnitrone 、 苯乙炔 在 CuI * pyridine potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以50%的产率得到1,3-Diphenyl-4-benzoyl-azetidinon-(2)
  参考文献：
  名称：

  Copper-Catalyzed Reaction of Terminal Alkynes with Nitrones. Selective Synthesis of 1-Aza-1-buten-3-yne and 2-Azetidinone Derivatives

  摘要：

  Reaction of arylacetylenes with C,N-diarylnitrones using a catalyst system of CuI-dppe (dppe = 1,2-bis(diphenylphosphino)ethane) in the presence of potassium carbonate in DMF predominantly affords the corresponding 1,2,4-triaryl-1-aza- 1-buten-3-ynes in good yields. In contrast, the catalytic reaction using CuI in the presence of an excess amount of pyridine as the ligand gives 1,3,4-triaryl-2-azetidinones as the major products. The reaction with aliphatic terminal alkynes in place of arylacetylenes produces the latter products irrespective of the catalyst system used. Asymmetric induction is also observed in the reaction of phenylacetylene with alpha,N-diphenylnitrone to give 1,2,4-triphenyl-2-azetidinone in the presence of chiral bisoxazoline-type ligands.

  DOI：

  10.1021/jo00121a018

文献信息

• Alcaide, Benito; Dominguez, Gema; Plumet, Joaquin, Heterocycles, 1988, vol. 27, # 6, p. 1317 - 1320
  作者：Alcaide, Benito、Dominguez, Gema、Plumet, Joaquin、Sierra, Miguel A.

  DOI：——

  日期：——
• Cu(I)/Bis(azaferrocene)-Catalyzed Enantioselective Synthesis of β-Lactams via Couplings of Alkynes with Nitrones
  作者：Michael M.-C. Lo、Gregory C. Fu

  DOI：10.1021/ja025833z

  日期：2002.5.1

  As a consequence of the wide-ranging significance of beta-lactams (e.g., use as drugs and as chiral building blocks), a great deal of effort has been dedicated to the development of methods for their stereoselective synthesis. Although considerable progress has been achieved, nearly all of the approaches that have been described are based on the use of chiral precursors; direct catalytic enantioselective routes to beta-lactams are rare as well as limited in scope. In this communication, we establish that, using a new C2-symmetric planar-chiral bis(azaferrocene) ligand, we can generate beta-lactams with very good enantiomeric excess and cis diastereoselection via catalytic enantioselective Kinugasa reactions (couplings of alkynes with nitrones). Appealing attributes of this process include the ready availability of the starting materials, the functional-group tolerance of the reaction, and the convergency of the approach.