{(3R,5S)-1-benzyl-5-[bis(3,5-dimethylphenyl)(hydroxy)methyl]pyrrolidin-3-yl} 5-bromopentanoate | 1262967-63-4

• 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: {(3R,5S)-1-benzyl-5-[bis(3,5-dimethylphenyl)(hydroxy)methyl]pyrrolidin-3-yl} 5-bromopentanoate
• CAS: 1262967-63-4
• 化学式: C₃₃H₄₀BrNO₃
• 分子量: 578.59
• InChiKey: STMCBGQCWMXVMS-JSOSNVBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.91
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-甲基咪唑 、 {(3R,5S)-1-benzyl-5-[bis(3,5-dimethylphenyl)(hydroxy)methyl]pyrrolidin-3-yl} 5-bromopentanoate 反应 0.17h， 以88%的产率得到1-{5-[(3R,5S)-1-benzyl-5(bis(3.5-dimethylphenyl)(hydroxy)methyl)pyrrolidin-3-yloxy]-5-oxopentyl}-3-methyl-1H-imidazol-3-ium bromide
  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
• 作为产物：
  描述：

  5-溴戊酸 、 (3R,5S)-1-benzyl-5-[bis(3,5-dimethylphenyl)(hydroxy)methyl]pyrrolidin-3-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 以97%的产率得到{(3R,5S)-1-benzyl-5-[bis(3,5-dimethylphenyl)(hydroxy)methyl]pyrrolidin-3-yl} 5-bromopentanoate
  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