benzyl (3S)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-hydroxyisoxazolidine-2-carboxylate | 1262967-93-0

• 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: benzyl (3S)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-hydroxyisoxazolidine-2-carboxylate
• CAS: 1262967-93-0
• 化学式: C₂₃H₂₇NO₆
• 分子量: 413.47
• InChiKey: BTMLHNVWBNDNAH-YDNXMHBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  77.46
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-(苄羰氧基)羟基胺 、 (E)-3-(3-(cyclopentyloxy)-4-methoxyphenyl)acrylaldehyde 在 3-(5-((3R,5S)-5-(diphenyl(trimethylsilyloxy)methyl)pyrrolidin-3-yloxy)-5-oxopentyl)-1-methyl-1H-imidazol-3-ium hexafluorophosphate 、 silica gel 作用下， 以 甲苯 、 正己烷 、 乙酸乙酯 为溶剂， 反应 48.0h， 生成 benzyl (3R)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-hydroxyisoxazolidine-2-carboxylate 、 benzyl (3S)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-hydroxyisoxazolidine-2-carboxylate
  参考文献：
  名称：

  α,α-Diarylprolinol-derived chiral ionic liquids: recoverable organocatalysts for the domino reaction between α,β-enals and N-protected hydroxylamines

  摘要：

  Chiral ionic liquids bearing alpha alpha-diarylprolinol units were synthesized and applied for the first time as organocatalysts for the domino reaction between alpha beta-enals and N-protected hydroxylamines involving aza-Michael and intramolecular acetalization steps Corresponding 5-hydroxy-3-arylisoxazolidines with either an (S)- or (R)-configuration at C-3 were obtained in excellent yields (up to 94%) and with moderate to high enantioselectivities (64 to >99% ee) The ionic liquid supported catalyst can be easily recycled and reused for at least four times without a significant loss of chemical yield or enantioselectivity (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.020