(1R,5R,7aR)-5-[4-(tert-butyl)benzyl]-1-methyltetrahydropyrrolo[1,2-c]oxazol-3(1H)-one | 1226916-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,5R,7aR)-5-[4-(tert-butyl)benzyl]-1-methyltetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
• 英文别名: (1R,5R,7aR)-5-[(4-tert-butylphenyl)methyl]-1-methyl-5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-3-one
• CAS: 1226916-04-6
• 化学式: C₁₈H₂₅NO₂
• 分子量: 287.402
• InChiKey: DYHNBRDLSPHSKD-DAXOMENPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  4-叔丁基溴苯 、 (+)-(4R,5R)-4-(but-3-en-1-yl)-5-methyloxazolidin-2-one 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 27.0h， 以71%的产率得到(1R,5R,7aR)-5-[4-(tert-butyl)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

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.