3-benzoyl-5-methoxy-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexane-1-carboxylic acid methyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 3-benzoyl-5-methoxy-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexane-1-carboxylic acid methyl ester
• 英文别名: Methyl 3-benzoyl-5-methoxy-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexane-1-carboxylate；methyl 3-benzoyl-5-methoxy-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexane-1-carboxylate
• 化学式: C₁₄H₁₃NO₆
• 分子量: 291.26
• InChiKey: GVTZYKAICUBCNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-苯甲酰基甘氨酸甲酯 在 rhodium(II) acetate dimer N-苯基马来酰亚胺 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 10.0h， 生成 3-benzoyl-5-methoxy-2-oxo-6-oxa-3-azabicyclo[3.1.0]hexane-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Site selectivity in the rhodium(II)-catalyzed reaction of α-diazoimides. Ligand and substituent effects

  摘要：

  The product distribution obtained from Rh(II)-catalyzed decomposition of alpha-diazoimides derived from glycine methyl ester has been found to be selectively controlled by the proper choice of catalyst. When the reaction was carried out using perfluorinated ligands, the diazoimide cyclized to produce an isomunchnone dipole whose formation could be monitored by NMR spectroscopy. Reaction of the dipole with a trapping agent such as N-phenylmaleimide resulted in the isolation of a 1,3-dipolar cycloadduct in high yield. The product distribution changed dramatically when rhodium(II)-acetate was employed as the catalyst. The products obtained from this reaction were derived from an azabicyclic epoxide intermediate. The catalyst effect can be modulated by the addition of Sc(OTf)(3) as a Lewis acid or by using nitromethane as the solvent. Changing the nature of the interacting carbonyl group had little effect on the cyclization pathways. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00479-1

文献信息

• Site selectivity in the rhodium(II)-catalyzed reaction of α-diazoimides. Ligand and substituent effects
  作者：Michael Prein、Peter J. Manley、Albert Padwa

  DOI：10.1016/s0040-4020(97)00479-1

  日期：1997.6

  The product distribution obtained from Rh(II)-catalyzed decomposition of alpha-diazoimides derived from glycine methyl ester has been found to be selectively controlled by the proper choice of catalyst. When the reaction was carried out using perfluorinated ligands, the diazoimide cyclized to produce an isomunchnone dipole whose formation could be monitored by NMR spectroscopy. Reaction of the dipole with a trapping agent such as N-phenylmaleimide resulted in the isolation of a 1,3-dipolar cycloadduct in high yield. The product distribution changed dramatically when rhodium(II)-acetate was employed as the catalyst. The products obtained from this reaction were derived from an azabicyclic epoxide intermediate. The catalyst effect can be modulated by the addition of Sc(OTf)(3) as a Lewis acid or by using nitromethane as the solvent. Changing the nature of the interacting carbonyl group had little effect on the cyclization pathways. (C) 1997 Elsevier Science Ltd.