benzyl (3S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate | 1262967-89-4

• 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: benzyl (3S)-5-hydroxy-3-phenylisoxazolidine-2-carboxylate
• 英文别名: benzyl (3S)-5-hydroxy-3-phenyl-1,2-oxazolidine-2-carboxylate
• CAS: 1262967-89-4
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: XZFLEFKXRXPSCF-VYRBHSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  反式肉桂醛 、 N-(苄羰氧基)羟基胺 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 24.0h， 以90%的产率得到benzyl (3S)-5-hydroxy-3-phenylisoxazolidine-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

文献信息

• α,α-Diarylprolinol-derived chiral ionic liquids: recoverable organocatalysts for the domino reaction between α,β-enals and N-protected hydroxylamines
  作者：Oleg V. Maltsev、Alexandr S. Kucherenko、Alexandr L. Chimishkyan、Sergei G. Zlotin

  DOI：10.1016/j.tetasy.2010.10.020

  日期：2010.11

  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