2-((3R,4S,5S)-5-Butyl-5-ethoxy-4-hydroxy-2-oxo-tetrahydro-furan-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester

• 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: 2-((3R,4S,5S)-5-Butyl-5-ethoxy-4-hydroxy-2-oxo-tetrahydro-furan-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-[(3R,4S,5S)-5-butyl-5-ethoxy-4-hydroxy-2-oxooxolan-3-yl]pyrrolidine-1-carboxylate
• 化学式: C₁₉H₃₃NO₆
• 分子量: 371.474
• InChiKey: GKECMGBSFRJWSE-SDMFIRNDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  85.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (3S,3aS,8aR,8bR)-3-Butyl-3-ethoxy-hexahydro-furo[3,4-d]pyrrolo[1,2-b]isoxazol-1-one 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以99%的产率得到2-((3R,4S,5S)-5-Butyl-5-ethoxy-4-hydroxy-2-oxo-tetrahydro-furan-3-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Asymmetric Functionalization of Chromium Carbene-Derived Optically Active 4,4-Disubstituted Butenolides

  摘要：

  Optically active 4,4-disubstituted butenolides were readily prepared by photolysis of chromium alkoxycarbene complexes with optically active ene carbamates, followed by Baeyer-Villiger oxidation/oxazolidinone elimination. These butenolides underwent clean 1,3-dipolar cycloaddition reactions with cyclic nitrones exclusively from the more hindered face of the butenolide. Azomethine ylides were considerably less stereoselective. Conjugate addition reactions also occurred from the more hindered face, while cis hydroxylation occurred from the opposite face.

  DOI：

  10.1021/jo00117a034

文献信息

• Asymmetric Functionalization of Chromium Carbene-Derived Optically Active 4,4-Disubstituted Butenolides
  作者：A. D. Reed、Louis S. Hegedus

  DOI：10.1021/jo00117a034

  日期：1995.6

  Optically active 4,4-disubstituted butenolides were readily prepared by photolysis of chromium alkoxycarbene complexes with optically active ene carbamates, followed by Baeyer-Villiger oxidation/oxazolidinone elimination. These butenolides underwent clean 1,3-dipolar cycloaddition reactions with cyclic nitrones exclusively from the more hindered face of the butenolide. Azomethine ylides were considerably less stereoselective. Conjugate addition reactions also occurred from the more hindered face, while cis hydroxylation occurred from the opposite face.