(+)-trans-1,4-diphenyl-3-N-(benzoylamino)-3-methylazetidin-2-one | 74185-87-8

• 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: (+)-trans-1,4-diphenyl-3-N-(benzoylamino)-3-methylazetidin-2-one
• 英文别名: trans-1,4-diphenyl-3-N-(benzoylamino)-3-methylazetidin-2-one；(-)-1,4-diphenyl-3-N-(benzoylamino)-3-methylazetidin-2-one；N-(3-methyl-2-oxo-1-diphenyl-azetidin-3-yl)-benzamide；3-Benzoylamino-3-methyl-1,4-diphenyl-2-azetidinone
• CAS: 74185-87-8
• 化学式: C₂₃H₂₀N₂O₂
• 分子量: 356.424
• InChiKey: QWMIJWONOJDVKF-REWPJTCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  49.41
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  N-(3-methyl-2-oxo-1,4-diphenyl-azetidin-3-yl)-phthalimide 在 盐酸 、 一水合肼 作用下， 以 吡啶 为溶剂， 反应 3.0h， 生成 (+)-trans-1,4-diphenyl-3-N-(benzoylamino)-3-methylazetidin-2-one
  参考文献：
  名称：

  Kumar, Pradeep; Mukerjee, Arya K., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 5, p. 420 - 421

  摘要：

  DOI：

文献信息

• Solid-Phase Synthesis of β-Lactams via the Ester Enolate−Imine Condensation Route
  作者：Stefan Schunk、Dieter Enders

  DOI：10.1021/ol0055465

  日期：2000.4.1

  The ester enolate-imine condensation route to beta-lactams via an immobilized ester enolate has been achieved for the first time. The key reaction in the synthesis is the cyclization of the resin bound ester dianion and an imine. Traceless cleavage from the T1-triazene linker system yields the desired beta-lactams.

  首次实现了通过固定化的酯烯酸酯的酯烯酸酯-亚胺缩合路线生成β-内酰胺。合成中的关键反应是树脂结合的酯二阴离子和亚胺的环化。从T1-三氮烯接头系统进行无痕切割可得到所需的β-内酰胺。
• Preparation of .beta.-lactams by the condensation of lithium ester enolates with aryl aldimines
  作者：Charles Gluchowski、Lynn Cooper、David E. Bergbreiter、Martin Newcomb

  DOI：10.1021/jo01305a008

  日期：1980.8
• Solid-Phase Synthesis of Monocyclic β-Lactam Derivatives
  作者：S. Schunk、D. Enders

  DOI：10.1021/jo0261552

  日期：2002.11.1

  Liquid-phase studies concerning the solid-phase synthesis of monocyclic beta-lactams via the esterenolate imine condensation route have been conducted utilizing triazene esters 1 and 2 as model compounds. Esters were attached to benzylamine resin 6 by a triazene linker employing the respective diazonium salts. Immobilized ester-enolates 8 and 10 were reacted with various imines and imine precursors to give polymer-bound beta-lactams 14 and 17 in different substitution patterns. Traceless cleavage from the triazene linker yields the desired beta-lactams 16 and 19.