(R)-3-Hydroxy-5-[(2S,3R)-3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-1-methyl-pyrrolidin-2-one | 474086-30-1

• 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: (R)-3-Hydroxy-5-[(2S,3R)-3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-1-methyl-pyrrolidin-2-one
• 英文别名: (5R)-3-hydroxy-5-[(2S,3R)-3-methoxy-1-(4-methoxyphenyl)-4-oxoazetidin-2-yl]-1-methylpyrrolidin-2-one
• CAS: 474086-30-1
• 化学式: C₁₆H₂₀N₂O₅
• 分子量: 320.345
• InChiKey: ZZPVLVKJFZSXNN-NIWMIYJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-3-Hydroxy-5-[(2S,3R)-3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-1-methyl-pyrrolidin-2-one 在 甲基磺酰氯 、 三乙胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 以80%的产率得到(R)-3-Chloro-5-[(2S,3R)-3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-1-methyl-pyrrolidin-2-one
  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：

  3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carbaldehyde 在 hexacarbonyl molybdenum 、 三乙胺 作用下， 以 甲苯 、 乙腈 、 苯 为溶剂， 反应 20.0h， 生成 (R)-3-Hydroxy-5-[(2S,3R)-3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidin-2-yl]-1-methyl-pyrrolidin-2-one
  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