N,α-bis(4-methoxyphenyl)nitrone | 34007-84-6

• 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: N,α-bis(4-methoxyphenyl)nitrone
• 英文别名: N-(4-methoxyphenyl)-α-(4-methoxyphenyl)nitrone；N,1-bis(4-methoxyphenyl)methanimine oxide
• CAS: 34007-84-6
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: ISARSZOYUAALQL-WJDWOHSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  47.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,α-bis(4-methoxyphenyl)nitrone 、 苯乙炔 在 (-)-(S,S)-bis(hexamethylazaferrocene)methylene 、 copper(l) chloride N-甲基二环己基胺 作用下， 以 乙腈 为溶剂， 反应 184.0h， 生成 trans-1,4-di(4-methoxyphenyl)-3-phenyl-2-azetidinone 、 (3S,4S)-1,4-bis(4-methoxyphenyl)-3-phenylazetidin-2-one 、 (3R,4R)-1,4-di(4-methoxyphenyl)-3-phenyl-2-azetidinone
  参考文献：
  名称：

  Cu(I)/Bis(azaferrocene)-Catalyzed Enantioselective Synthesis of β-Lactams via Couplings of Alkynes with Nitrones

  摘要：

  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.

  DOI：

  10.1021/ja025833z
• 作为产物：
  描述：

  4-硝基苯甲醚 、 4-甲氧基苯甲醛 在 platinum on activated charcoal 甲烷磺酸 、 氢气 、 亚磷酸三乙酯 作用下， 以12%的产率得到N,α-bis(4-methoxyphenyl)nitrone
  参考文献：
  名称：

  Cu(I)/Bis(azaferrocene)-Catalyzed Enantioselective Synthesis of β-Lactams via Couplings of Alkynes with Nitrones

  摘要：

  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.

  DOI：

  10.1021/ja025833z