1-(3-oxa-2-azabicyclo[2.2.2]oct-5-en-2-yl)heptan-1-one

• 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: 1-(3-oxa-2-azabicyclo[2.2.2]oct-5-en-2-yl)heptan-1-one
• 英文别名: 1-(2-Oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl)heptan-1-one；1-(2-oxa-3-azabicyclo[2.2.2]oct-5-en-3-yl)heptan-1-one
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: RDBQEBYOAXKTRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  庚烷氧肟酸 、 1,3-环己二烯 在 t-BOOH 作用下， 以 癸烷 、 二氯甲烷 为溶剂， 反应 1.0h， 以48%的产率得到1-(3-oxa-2-azabicyclo[2.2.2]oct-5-en-2-yl)heptan-1-one
  参考文献：
  名称：

  Dual Function Catalysts. Dehydrogenation and Asymmetric Intramolecular Diels−Alder Cycloaddition of N-Hydroxy Formate Esters and Hydroxamic Acids:  Evidence for a Ruthenium−Acylnitroso Intermediate

  摘要：

  The chiral ruthenium salen complex, 13b, functions as an efficient catalyst for the sequential oxidation and asymmetric Diels-Alder cycloaddition of hydroxamic acids and N-hydroxy formate esters. This result provides evidence for the formation of a ruthenium-nitroso formate (acyl nitroso) intermediate. The Diels-Alder precursors are prepared from simple building blocks, and the cycloadducts, bridged oxazinolactams, can serve as useful intermediates in organic synthesis.

  DOI：

  10.1021/ja050059b

文献信息

• The mild oxidation of nitrile oxides affords a convenient entry to nitrosocarbonyl intermediates, versatile tools in organic syntheses
  作者：P. Quadrelli、M. Mella、A. Gamba Invernizzi、P. Caramella

  DOI：10.1016/s0040-4020(99)00574-8

  日期：1999.8

  Nitrile oxides are oxidized by tertiary amine N-oxides in different solvents at room temperature to afford in the presence of dienes nitrosocarbonyl adducts in fair yields. The mild conditions used in oxidizing a variety of nitrile oxides promise a wide application of this method in synthetic processes.

  在室温下，在不同的溶剂中，叔丁胺N-氧化物将腈氧化物氧化，在二烯亚硝基羰基加合物的存在下以合理的收率提供。用于氧化多种腈氧化物的温和条件使该方法在合成过程中得到广泛应用。
• Dual Function Catalysts. Dehydrogenation and Asymmetric Intramolecular Diels−Alder Cycloaddition of <i>N</i>-Hydroxy Formate Esters and Hydroxamic Acids:  Evidence for a Ruthenium−Acylnitroso Intermediate
  作者：Chun P. Chow、Kenneth J. Shea

  DOI：10.1021/ja050059b

  日期：2005.3.1

  The chiral ruthenium salen complex, 13b, functions as an efficient catalyst for the sequential oxidation and asymmetric Diels-Alder cycloaddition of hydroxamic acids and N-hydroxy formate esters. This result provides evidence for the formation of a ruthenium-nitroso formate (acyl nitroso) intermediate. The Diels-Alder precursors are prepared from simple building blocks, and the cycloadducts, bridged oxazinolactams, can serve as useful intermediates in organic synthesis.