4-methyl-8-oxo-2-(phenylmethoxy)-2-azabicyclo[3.2.1]oct-6-en-3-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吖庚因类
• 英文名称: 4-methyl-8-oxo-2-(phenylmethoxy)-2-azabicyclo[3.2.1]oct-6-en-3-one
• 英文别名: (+/-)-(4S,5R,1S)4-methyl-8-oxo-2-(phenylmethoxy)-2-azabicyclo[3.2.1]oct-6-en-3-one；(1S,4S,5R)-4-methyl-2-phenylmethoxy-8-oxa-2-azabicyclo[3.2.1]oct-6-en-3-one
• 化学式: C₁₄H₁₅NO₃
• 分子量: 245.278
• InChiKey: QFHOABUNZRCIBR-UHTWSYAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苄氧基胺盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 、 2,2,2-三氟乙醇 为溶剂， 反应 16.0h， 生成 4-methyl-8-oxo-2-(phenylmethoxy)-2-azabicyclo[3.2.1]oct-6-en-3-one
  参考文献：
  名称：

  Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4 + 3] Cycloaddition Reactions for Heterocycle Synthesis

  摘要：

  Aza-[4 + 3] cycloadditions of putative azaoxyallyl cationic intermediates and cyclic dienes are reported. The intermediate is generated by the dehydrohalogenation of alpha-haloamides. The reaction is general to a variety of alpha-haloamides and is diastereoselective. Computational and experimental data suggest that an N-alkoxy substituent stabilizes the aza-oxyallyl cationic intermediate.

  DOI：

  10.1021/ja201901d

文献信息

• NITROGEN-CONTAINING HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING THE SAME
  申请人：Jeffrey Christopher S.

  公开号：US20120271046A1

  公开（公告）日：2012-10-25

  The present invention relates to 7-membered nitrogen-containing heterocyclic compounds and methods of making the same. Using a novel aza-[4+3] cycloaddition reaction, the 7-membered heterocyclic compounds are synthesized by reacting a first reactant and a second reactant. Exemplary first reactants and second reactants include α-halohydroxamates and dienes, respectively.

  本发明涉及7-成员含氮杂环化合物及其制备方法。利用一种新颖的aza-[4+3]环加成反应，通过将第一反应物和第二反应物反应合成了7-成员杂环化合物。示例中的第一反应物和第二反应物包括α-卤羟羟肟酸酯和二烯。
• US9163033B2
  申请人：——

  公开号：US9163033B2

  公开（公告）日：2015-10-20
• Generation and Reactivity of Aza-Oxyallyl Cationic Intermediates: Aza-[4 + 3] Cycloaddition Reactions for Heterocycle Synthesis
  作者：Christopher S. Jeffrey、Korry L. Barnes、John A. Eickhoff、Christopher R. Carson

  DOI：10.1021/ja201901d

  日期：2011.5.25

  Aza-[4 + 3] cycloadditions of putative azaoxyallyl cationic intermediates and cyclic dienes are reported. The intermediate is generated by the dehydrohalogenation of alpha-haloamides. The reaction is general to a variety of alpha-haloamides and is diastereoselective. Computational and experimental data suggest that an N-alkoxy substituent stabilizes the aza-oxyallyl cationic intermediate.