5-methyl-6a-phenylhexahydro-6H-pyrrolo[3,4-c]isoxazol-6-one

• 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-6H-pyrrolo[3,4-c]isoxazol-6-one
• 英文别名: (3aR,6aS)-5-methyl-6a-phenyl-1,3,3a,4-tetrahydropyrrolo[3,4-c][1,2]oxazol-6-one
• 化学式: C₁₂H₁₄N₂O₂
• 分子量: 218.255
• InChiKey: GMZFREFVDFJAGQ-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  D(+)-10-樟脑磺酸 、 5-methyl-6a-phenylhexahydro-6H-pyrrolo[3,4-c]isoxazol-6-one 以 丙酮 为溶剂， 以93%的产率得到5-methyl-6-oxo-6a-phenylhexahydro-1H-pyrrolo[3,4-c][1,2]oxazol-1-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：

  氧代(苯基)乙酰氯 在 吡啶 、 盐酸羟胺 、 碳酸氢钠 、 对苯二酚 作用下， 以 乙醇 、 二氯甲烷 、 xylene 为溶剂， 反应 40.0h， 生成 5-methyl-6a-phenylhexahydro-6H-pyrrolo[3,4-c]isoxazol-6-one
  参考文献：
  名称：

  α-酮酰胺作为杂环的前体-哌嗪5酮硝酮的生成和环加成反应。

  摘要：

  发现由丙酮酸或苯甲酰基甲酸与烯丙基胺反应形成的α-酮酰胺10a，b以单一的旋转异构体形式存在，而它们的叔酰胺类似物10c，d在室温下以两种旋转异构体的形式存在。羟基亚氨基衍生物8具有其母体的构象特征。可以看出，新的α-酰胺肟的几何结构取决于起始酸的结构和酰胺基的取代程度。衍生自丙酮酸和烯丙胺的肟8a仅作为（E）-异构体形成，而其叔酰胺类似物8c既作为（E）-异构体也形成（Z）异构体。衍生自苯甲酰基甲酸的肟具有相反的选择性，两种几何异构体均由仲酰胺8b形成，而只有（Z）-异构体由叔酰胺8d形成。除8b外，所有肟的构型均稳定，其中（Z）-异构体反应形成异恶唑并吡咯烷酮11-具有相对稀少的双环核的化合物，并且（E）-异构体环化成哌嗪-5-一硝基1-酮哌嗪N迄今为止，氧化物在文献中仅出现过一次。新的硝基化合物被苯基乙烯基砜，乙炔二甲酸二甲酯和丙炔酸甲酯截留，生成异恶唑烷和异恶唑啉稠合的哌嗪酮13、

  DOI：

  10.1039/b210943n

文献信息

• 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.
• α-Keto amides as precursors to heterocycles—generation and cycloaddition reactions of piperazin-5-one nitrones
  作者：Frances Heaney、Julie Fenlon、Patrick McArdle、Desmond Cunningham

  DOI：10.1039/b210943n

  日期：2003.3.27

  acid and allyl amine is formed solely as the (E)-isomer whilst its tertiary amido analogue 8c is formed as both (E)- and (Z)-isomers. Oximes derived from benzoylformic acid have the opposite selectivity with both geometrical isomers forming from the secondary amide 8b and only the (Z)-isomer from the tertiary amide 8d. With the exception of 8b all oximes were configurationally stable with (Z)-isomers

  发现由丙酮酸或苯甲酰基甲酸与烯丙基胺反应形成的α-酮酰胺10a，b以单一的旋转异构体形式存在，而它们的叔酰胺类似物10c，d在室温下以两种旋转异构体的形式存在。羟基亚氨基衍生物8具有其母体的构象特征。可以看出，新的α-酰胺肟的几何结构取决于起始酸的结构和酰胺基的取代程度。衍生自丙酮酸和烯丙胺的肟8a仅作为（E）-异构体形成，而其叔酰胺类似物8c既作为（E）-异构体也形成（Z）异构体。衍生自苯甲酰基甲酸的肟具有相反的选择性，两种几何异构体均由仲酰胺8b形成，而只有（Z）-异构体由叔酰胺8d形成。除8b外，所有肟的构型均稳定，其中（Z）-异构体反应形成异恶唑并吡咯烷酮11-具有相对稀少的双环核的化合物，并且（E）-异构体环化成哌嗪-5-一硝基1-酮哌嗪N迄今为止，氧化物在文献中仅出现过一次。新的硝基化合物被苯基乙烯基砜，乙炔二甲酸二甲酯和丙炔酸甲酯截留，生成异恶唑烷和异恶唑啉稠合的哌嗪酮13、