(4S*,5R*)-4-(but-3-en-1-yl)-5-methyloxazolidin-2-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4S*,5R*)-4-(but-3-en-1-yl)-5-methyloxazolidin-2-one
• 英文别名: (4S,5R)-4-but-3-enyl-5-methyl-1,3-oxazolidin-2-one
• 化学式: C₈H₁₃NO₂
• 分子量: 155.197
• InChiKey: FLIRLMJPHASERS-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4S*,5R*)-4-(but-3-en-1-yl)-5-methyloxazolidin-2-one 、 4-溴-N,N-二甲基苯胺 在 palladium diacetate 、 sodium t-butanolate 、 2-二环己基磷-2',6'-二异丙氧基-1,1'-联苯 作用下， 以 苯 为溶剂， 反应 7.0h， 以70%的产率得到(1R*,5S*,7aS*)-5-[4-(Dimethylamino)benzyl]-1-methyltetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
  参考文献：
  名称：

  Pd-Catalyzed Carboamination of Oxazolidin-2-ones: A Stereoselective Route to trans-2,5-Disubstituted Pyrrolidines

  摘要：

  Palladium-catalyzed carboamination reactions between aryl bromides and 4-(but-3-enyl)-substituted oxazolidin-2-ones are described. These transformations afford bicyclic oxazolidin-2-one derivatives that can be converted to trans-2,5-disubstituted pyrrolidines in one step. The starting materials are easily prepared from amino acid precursors, and products that contain up to three stereocenters are generated with >20:1 dr.

  DOI：

  10.1021/ol1006828
• 作为产物：
  描述：

  (2R*,3S*)-tert-butyl 2-hydroxyhept-6-en-3-ylcarbamate 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 1.0h， 以97%的产率得到(4S*,5R*)-4-(but-3-en-1-yl)-5-methyloxazolidin-2-one
  参考文献：
  名称：

  Pd-Catalyzed Carboamination of Oxazolidin-2-ones: A Stereoselective Route to trans-2,5-Disubstituted Pyrrolidines

  摘要：

  Palladium-catalyzed carboamination reactions between aryl bromides and 4-(but-3-enyl)-substituted oxazolidin-2-ones are described. These transformations afford bicyclic oxazolidin-2-one derivatives that can be converted to trans-2,5-disubstituted pyrrolidines in one step. The starting materials are easily prepared from amino acid precursors, and products that contain up to three stereocenters are generated with >20:1 dr.

  DOI：

  10.1021/ol1006828

文献信息

• Pd-Catalyzed Carboamination of Oxazolidin-2-ones: A Stereoselective Route to <i>trans</i>-2,5-Disubstituted Pyrrolidines
  作者：Georgia S. Lemen、John P. Wolfe

  DOI：10.1021/ol1006828

  日期：2010.5.21

  Palladium-catalyzed carboamination reactions between aryl bromides and 4-(but-3-enyl)-substituted oxazolidin-2-ones are described. These transformations afford bicyclic oxazolidin-2-one derivatives that can be converted to trans-2,5-disubstituted pyrrolidines in one step. The starting materials are easily prepared from amino acid precursors, and products that contain up to three stereocenters are generated with >20:1 dr.