(1S,5R)-tert-butyl 3-oxo-2,4-diazabicyclo[3.2.0]-heptane-2-carboxylate | 1226907-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂卓
• 英文名称: (1S,5R)-tert-butyl 3-oxo-2,4-diazabicyclo[3.2.0]-heptane-2-carboxylate
• 英文别名: tert-butyl (1S,5R)-3-oxo-2,4-diazabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 1226907-31-8
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: JJGRTZWWZUYYCU-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1R,2S)-2-[[叔丁氧羰基]氨基]环丁烷羧酸 在 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 甲苯 为溶剂， 以68%的产率得到(1S,5R)-tert-butyl 3-oxo-2,4-diazabicyclo[3.2.0]-heptane-2-carboxylate
  参考文献：
  名称：

  Synthesis and structural features of cyclobutane-containing chiral bicyclic ureas

  摘要：

  Efficient and stereoselective synthetic routes have been developed for the preparation of chiral N-mono-protected cyclobutane bicyclic ureas in which one of the NH groups is protected as a benzyl or tert-butyl carbamate. Ureas in both enantiomeric forms were obtained from a common chiral precursor via the selective manipulation of functional groups. These compounds have been subjected to a structural study in solution and in the solid state. NMR, IR and TEM techniques evidence a strong tendency to aggregation in solution giving regular assemblies, which is a result of intermolecular urea N-H center dot center dot center dot O=C hydrogen bonding. In the solid state, X-ray analysis shows that two urea molecules interact through only one hydrogen bond yielding infinite chains. This fact and the almost complete coplanarity of both the urea and the carbamate carbonyl groups determine the crystal packing to be formed by a parallel molecular arrangement. All these structural features are well supported by theoretical calculations that allow us to conclude that the formation of a network based on hydrogen bonding is energetically favourable. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.01.020

文献信息

• Synthesis and structural features of cyclobutane-containing chiral bicyclic ureas
  作者：Esther Gorrea、Pau Nolis、Ángel Álvarez-Larena、Eric Da Silva、Vicenç Branchadell、Rosa M. Ortuño

  DOI：10.1016/j.tetasy.2010.01.020

  日期：2010.3

  Efficient and stereoselective synthetic routes have been developed for the preparation of chiral N-mono-protected cyclobutane bicyclic ureas in which one of the NH groups is protected as a benzyl or tert-butyl carbamate. Ureas in both enantiomeric forms were obtained from a common chiral precursor via the selective manipulation of functional groups. These compounds have been subjected to a structural study in solution and in the solid state. NMR, IR and TEM techniques evidence a strong tendency to aggregation in solution giving regular assemblies, which is a result of intermolecular urea N-H center dot center dot center dot O=C hydrogen bonding. In the solid state, X-ray analysis shows that two urea molecules interact through only one hydrogen bond yielding infinite chains. This fact and the almost complete coplanarity of both the urea and the carbamate carbonyl groups determine the crystal packing to be formed by a parallel molecular arrangement. All these structural features are well supported by theoretical calculations that allow us to conclude that the formation of a network based on hydrogen bonding is energetically favourable. (C) 2010 Elsevier Ltd. All rights reserved.