(+)-(3R,4S)-4-({[4-(dimethylamino)phenyl]imino}methyl)-3-methoxy-1-(4-methoxyphenyl)azetidin-2-one

• 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: (+)-(3R,4S)-4-({[4-(dimethylamino)phenyl]imino}methyl)-3-methoxy-1-(4-methoxyphenyl)azetidin-2-one
• 英文别名: (3R,4S)-4-[[4-(dimethylamino)phenyl]iminomethyl]-3-methoxy-1-(4-methoxyphenyl)azetidin-2-one
• 化学式: C₂₀H₂₃N₃O₃
• 分子量: 353.421
• InChiKey: XQEFIKOJPPJWSK-RBUKOAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(3R,4S)-4-({[4-(dimethylamino)phenyl]imino}methyl)-3-methoxy-1-(4-methoxyphenyl)azetidin-2-one 在 氰化四丁基铵 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以53%的产率得到(+)-(3R)-5-{[4-(dimethylamino)phenyl]imino}-3-methoxy-1-(4-methoxyphenyl)-pyrrolidin-2-one
  参考文献：
  名称：

  Organocatalytic Ring Expansion of β-Lactams to γ-Lactams through a Novel N1−C4 Bond Cleavage. Direct Synthesis of Enantiopure Succinimide Derivatives

  摘要：

  Tetrabutylammonium cyanide (20 mol %) catalyzes ring expansion of 4-(arylimino)methylazetidin-2-ones 2 to 5-aryliminopyrrolidin-2-ones 3 through a novel N1-C4 bond cleavage of the beta-lactam nucleus. New, efficient one-pot protocols to enantiopure succinimide derivatives 3 and 4 from beta-lactam aldehydes 1 have also been developed.

  DOI：

  10.1021/ol051504a
• 作为产物：
  描述：

  N,N-二甲基-对苯二胺 、 3-methoxy-1-(4-methoxy-phenyl)-4-oxo-azetidine-2-carbaldehyde 在 4 A molecular sieve 作用下， 以 苯 为溶剂， 反应 5.5h， 以100%的产率得到(+)-(3R,4S)-4-({[4-(dimethylamino)phenyl]imino}methyl)-3-methoxy-1-(4-methoxyphenyl)azetidin-2-one
  参考文献：
  名称：

  Organocatalytic Ring Expansion of β-Lactams to γ-Lactams through a Novel N1−C4 Bond Cleavage. Direct Synthesis of Enantiopure Succinimide Derivatives

  摘要：

  Tetrabutylammonium cyanide (20 mol %) catalyzes ring expansion of 4-(arylimino)methylazetidin-2-ones 2 to 5-aryliminopyrrolidin-2-ones 3 through a novel N1-C4 bond cleavage of the beta-lactam nucleus. New, efficient one-pot protocols to enantiopure succinimide derivatives 3 and 4 from beta-lactam aldehydes 1 have also been developed.

  DOI：

  10.1021/ol051504a

文献信息

• Organocatalytic Ring Expansion of β-Lactams to γ-Lactams through a Novel N1−C4 Bond Cleavage. Direct Synthesis of Enantiopure Succinimide Derivatives
  作者：Benito Alcaide、Pedro Almendros、Gema Cabrero、M. Pilar Ruiz

  DOI：10.1021/ol051504a

  日期：2005.9.1

  Tetrabutylammonium cyanide (20 mol %) catalyzes ring expansion of 4-(arylimino)methylazetidin-2-ones 2 to 5-aryliminopyrrolidin-2-ones 3 through a novel N1-C4 bond cleavage of the beta-lactam nucleus. New, efficient one-pot protocols to enantiopure succinimide derivatives 3 and 4 from beta-lactam aldehydes 1 have also been developed.