5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c]isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c]isoxazole
• 英文别名: (3aS,6aR)-5-methyl-6a-phenyl-3,3a,4,6-tetrahydro-1H-pyrrolo[3,4-c][1,2]oxazole
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: RXXUCXBVXKQWMT-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  24.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c]isoxazole 、 D(+)-10-樟脑磺酸 以 丙酮 为溶剂， 以100%的产率得到5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c][1,2]oxazol-5-ium (7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methane sulfonate
  参考文献：
  名称：

  NH-Isoxazolo-bicycles; new molecular scaffolds for organocatalysis

  摘要：

  A new scaffold for organocatalysis of the Diels-Alder reaction is disclosed; an isoxazolidine ring forms the core of the catalyst and its activity is enhanced by judicious fusion of a second five-membered heterocycle to the c-edge. The catalyst performance is improved by the incorporation of an endo-cyclic electron withdrawing group adjacent to the fusion point. The organic core is effective only in the presence of an acid co-catalyst and whilst the two-component system shows potential as an enantioselective catalyst it is demonstrated that stereocontrol is a feature of the organic core and is fully independent of the choice of co-catalyst. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.034
• 作为产物：
  描述：

  2-[allyl(methyl)amino]-1-phenyl-1-ethanone oxime 以 甲苯 为溶剂， 反应 15.0h， 以62%的产率得到5-methyl-6a-phenylhexahydro-1H-pyrrolo[3,4-c]isoxazole
  参考文献：
  名称：

  δ-烯基肟的构效关系研究；竞争性热反应，导致环硝酮和/或N-未取代的双环异恶唑烷

  摘要：

  C-芳基δ-烯基肟的热反应通过分子内肟环烯烃加成途径（IOOC）和/或通过氮杂苯丙氨酸环转移（APT）途径的环状硝酮，产生N-未取代的双环内酯，内酰胺和吡咯烷稠合的异恶唑烷；许多因素，包括芳基的性质，肟的几何形状以及肟和末端烯烃之间的连接基的结构，都对竞争产生了影响。

  DOI：

  10.1016/j.tet.2010.06.005

文献信息

• An investigation of structure-reactivity relationships of δ-alkenyl oximes; competitive thermal reactions leading to cyclic nitrones and/or N-unsubstituted bicyclic isoxazolidines
  作者：Linda Doyle、Frances Heaney

  DOI：10.1016/j.tet.2010.06.005

  日期：2010.8

  Thermal reactions of C-aryl δ-alkenyl oximes give N-unsubstituted bicylic lactone, lactam and pyrrolidine fused isoxazolidines by an intramolecular oxime olefin cycloaddition pathway (IOOC) and/or cyclic nitrones by an azaprotio cyclotransfer (APT) route; a number of factors, including the nature of the aryl group, the oxime geometry and the structure of the linker between the oxime and the terminal

  C-芳基δ-烯基肟的热反应通过分子内肟环烯烃加成途径（IOOC）和/或通过氮杂苯丙氨酸环转移（APT）途径的环状硝酮，产生N-未取代的双环内酯，内酰胺和吡咯烷稠合的异恶唑烷；许多因素，包括芳基的性质，肟的几何形状以及肟和末端烯烃之间的连接基的结构，都对竞争产生了影响。
• NH-Isoxazolo-bicycles; new molecular scaffolds for organocatalysis
  作者：Linda Doyle、Frances Heaney

  DOI：10.1016/j.tet.2011.01.034

  日期：2011.3

  A new scaffold for organocatalysis of the Diels-Alder reaction is disclosed; an isoxazolidine ring forms the core of the catalyst and its activity is enhanced by judicious fusion of a second five-membered heterocycle to the c-edge. The catalyst performance is improved by the incorporation of an endo-cyclic electron withdrawing group adjacent to the fusion point. The organic core is effective only in the presence of an acid co-catalyst and whilst the two-component system shows potential as an enantioselective catalyst it is demonstrated that stereocontrol is a feature of the organic core and is fully independent of the choice of co-catalyst. (C) 2011 Elsevier Ltd. All rights reserved.