[3S,5S,7aR]-5-isopropyl-3-phenyl-hexahydropyrrolo[2,1-b]oxazole | 1071227-13-8

• 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: [3S,5S,7aR]-5-isopropyl-3-phenyl-hexahydropyrrolo[2,1-b]oxazole
• 英文别名: (3S,5S,7aR)-3-phenyl-5-propan-2-yl-2,3,5,6,7,7a-hexahydropyrrolo[2,1-b][1,3]oxazole
• CAS: 1071227-13-8
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: RDUIHCDXUXDMAW-RRFJBIMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [3S,5S,7aR]-5-isopropyl-3-phenyl-hexahydropyrrolo[2,1-b]oxazole 、 正丁基氯化镁 在 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(2S)-2-((2R,5S)-2-butyl-5-isopropylpyrrolidin-1-yl)-2-phenylethanol
  参考文献：
  名称：

  Short Enantioselective Syntheses of trans-5-Alkylprolines from New Functionalized Amino Alcohols

  摘要：

  GraphicsAmino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.

  DOI：

  10.1021/jo8014243
• 作为产物：
  描述：

  (2S)-2-((1S)-1-isopropyl-4-methoxybut-3-enylamino)-2-phenylethanol 在 硫酸 、 sodium hydroxide 作用下， 以 乙醚 、 水 为溶剂， 以100%的产率得到[3S,5S,7aR]-5-isopropyl-3-phenyl-hexahydropyrrolo[2,1-b]oxazole
  参考文献：
  名称：

  Short Enantioselective Syntheses of trans-5-Alkylprolines from New Functionalized Amino Alcohols

  摘要：

  GraphicsAmino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.

  DOI：

  10.1021/jo8014243

文献信息

• Palladium-Catalyzed Cyclization of Unsaturated β-Amino Alcohols: A New Access to Enantiopure Bicyclic Oxazolidines
  作者：Jeanne Alladoum、Emmanuel Vrancken、Pierre Mangeney、Sylvain Roland、Catherine Kadouri-Puchot

  DOI：10.1021/ol901375w

  日期：2009.8.20

  Chiral unsaturated beta-amino alcohols possessing a dialkylamino function cyclize in the presence of Pd(II) catalysts and reoxidants to afford enantiopure bicyclic oxazolidines with total regio- and stereocontrol. The scope and limitations of this transformation have been studied.
• Short Enantioselective Syntheses of <i>trans</i>-5-Alkylprolines from New Functionalized Amino Alcohols
  作者：Jeanne Alladoum、Sylvain Roland、Emmanuel Vrancken、Pierre Mangeney、Catherine Kadouri-Puchot

  DOI：10.1021/jo8014243

  日期：2008.12.19

  GraphicsAmino alcohols, having an enol ether function, cyclized in acidic medium to give quantitatively diastereosomerically pure bicyclic compounds that were transformed in five steps in enantiopure trans-5-alkylproline derivatives.