N-benzyl-1-[(2S,3R)-3-methoxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]methanimine oxide | 474086-03-8

• 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: N-benzyl-1-[(2S,3R)-3-methoxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]methanimine oxide
• CAS: 474086-03-8
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: GDYVBSAIAQOBRV-HUKQRPNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzyl-1-[(2S,3R)-3-methoxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]methanimine oxide 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 8.0h， 生成 dimethyl (3R,4S,5R)-2-benzyl-3-[(1S,2R)-2,3-dimethoxy-1-(4-methoxyanilino)-3-oxopropyl]-1,2-oxazolidine-4,5-dicarboxylate
  参考文献：
  名称：

  Efficient Entry to Highly Functionalized β-Lactams by Regio- and Stereoselective 1,3-Dipolar Cycloaddition Reaction of 2-Azetidinone-Tethered Nitrones. Synthetic Applications

  摘要：

  Racemic as well as optically pure 2-azetidinone-tethered nitrones, both cyclic and acyclic, were smoothly prepared from 4-oxoazetidine-2-carbaldehydes. The regio- and diastereoselectivities of the intermolecular 1,3-dipolar cycloaddition reactions of 2-azetidinone-tethered nitrones with substituted alkenes and alkynes were investigated. 2-Azetidinone-tethered nitrones on reacting with various dipolarophiles yielded isoxazolinyl-, isoxazolidinyl-, or fused polycyclic-beta-lactams, exhibiting good regio- and facial stereoselectivity in the most of the cases. In addition, some interesting transformations of these cycloadducts were performed, yielding aziridinyl beta-lactams or functionalized beta-alkoxycarbonyl gamma-lactams (derivatives of the aza analogue of paraconic acid).

  DOI：

  10.1021/jo025924e
• 作为产物：
  描述：

  N-苄基羟胺盐酸盐 、 3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carbaldehyde 在 三乙胺 作用下， 以 苯 为溶剂， 反应 16.0h， 以86%的产率得到N-benzyl-1-[(2S,3R)-3-methoxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]methanimine oxide
  参考文献：
  名称：

  Efficient Entry to Highly Functionalized β-Lactams by Regio- and Stereoselective 1,3-Dipolar Cycloaddition Reaction of 2-Azetidinone-Tethered Nitrones. Synthetic Applications

  摘要：

  Racemic as well as optically pure 2-azetidinone-tethered nitrones, both cyclic and acyclic, were smoothly prepared from 4-oxoazetidine-2-carbaldehydes. The regio- and diastereoselectivities of the intermolecular 1,3-dipolar cycloaddition reactions of 2-azetidinone-tethered nitrones with substituted alkenes and alkynes were investigated. 2-Azetidinone-tethered nitrones on reacting with various dipolarophiles yielded isoxazolinyl-, isoxazolidinyl-, or fused polycyclic-beta-lactams, exhibiting good regio- and facial stereoselectivity in the most of the cases. In addition, some interesting transformations of these cycloadducts were performed, yielding aziridinyl beta-lactams or functionalized beta-alkoxycarbonyl gamma-lactams (derivatives of the aza analogue of paraconic acid).

  DOI：

  10.1021/jo025924e

文献信息

• Efficient Entry to Highly Functionalized β-Lactams by Regio- and Stereoselective 1,3-Dipolar Cycloaddition Reaction of 2-Azetidinone-Tethered Nitrones. Synthetic Applications
  作者：Benito Alcaide、Pedro Almendros、Jose M. Alonso、Moustafa F. Aly、Carmen Pardo、Elena Sáez、M. Rosario Torres

  DOI：10.1021/jo025924e

  日期：2002.10.1

  Racemic as well as optically pure 2-azetidinone-tethered nitrones, both cyclic and acyclic, were smoothly prepared from 4-oxoazetidine-2-carbaldehydes. The regio- and diastereoselectivities of the intermolecular 1,3-dipolar cycloaddition reactions of 2-azetidinone-tethered nitrones with substituted alkenes and alkynes were investigated. 2-Azetidinone-tethered nitrones on reacting with various dipolarophiles yielded isoxazolinyl-, isoxazolidinyl-, or fused polycyclic-beta-lactams, exhibiting good regio- and facial stereoselectivity in the most of the cases. In addition, some interesting transformations of these cycloadducts were performed, yielding aziridinyl beta-lactams or functionalized beta-alkoxycarbonyl gamma-lactams (derivatives of the aza analogue of paraconic acid).