(+)-(3R)-3-methoxy-1-(4-methoxyphenyl)-5-[(4-methoxyphenyl)imino]pyrrolidin-2-one | 865357-59-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (+)-(3R)-3-methoxy-1-(4-methoxyphenyl)-5-[(4-methoxyphenyl)imino]pyrrolidin-2-one
• 英文别名: (3R)-3-methoxy-1-(4-methoxyphenyl)-5-(4-methoxyphenyl)iminopyrrolidin-2-one
• CAS: 865357-59-1
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: LENBSGXKRPOOPV-QGZVFWFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-(3R)-3-methoxy-1-(4-methoxyphenyl)-5-[(4-methoxyphenyl)imino]pyrrolidin-2-one 在 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 4.5h， 以55 mg的产率得到(+)-(3R)-3-methoxy-1-(4-methoxyphenyl)pyrrolidine-2,5-dione
  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：

  (3R,4S)-3-methoxy-1-(4-methoxyphenyl)-4-[(4-methoxyphenyl)iminomethyl]azetidin-2-one 在 氰化四丁基铵 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以64%的产率得到(+)-(3R)-3-methoxy-1-(4-methoxyphenyl)-5-[(4-methoxyphenyl)imino]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

文献信息

• Stereoselective cyanation of 4-formyl and 4-imino-?-lactams: application to the synthesis of polyfunctionalized ?-lactams
  作者：Benito Alcaide、Pedro Almendros、Gema Cabrero、M. Pilar Ruiz

  DOI：10.1016/j.tet.2012.02.062

  日期：2012.12

  The stereoselective reaction of 4-oxoazetidine-2-carbaldehydes and their corresponding imines with cyanide-based reagents give β-lactam α-aminonitriles, which are chameleonic building blocks for the controlled synthesis of a variety of new compounds including functionalized γ-lactams, succinimide derivatives, and diamino-lactams derivatives in optically pure form.

  4-氧杂氮杂环丁烷-2-甲醛及其相应的亚胺与氰基试剂的立体选择性反应产生β-内酰胺α-氨基腈，它们是香豆油的结构单元，可控制合成各种新化合物，包括官能化的γ-内酰胺，琥珀酰亚胺衍生物和光学纯形式的二氨基-内酰胺衍生物。
• 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.