1-{5-[(3R,5S)-5-(bis(3.5-dimethylphenyl)(hydroxy)methyl)pyrrolidin-3-yloxy]-5-oxopentyl}-3-methyl-1H-imidazol-3-ium bromide | 1262967-68-9

• 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: 1-{5-[(3R,5S)-5-(bis(3.5-dimethylphenyl)(hydroxy)methyl)pyrrolidin-3-yloxy]-5-oxopentyl}-3-methyl-1H-imidazol-3-ium bromide
• CAS: 1262967-68-9
• 化学式: Br*C₃₀H₄₀N₃O₃
• 分子量: 570.57
• InChiKey: UYWWGYFPNSZQJB-CNORLSDQSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.93
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  67.37
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 1-{5-[(3R,5S)-5-(bis(3.5-dimethylphenyl)(hydroxy)methyl)pyrrolidin-3-yloxy]-5-oxopentyl}-3-methyl-1H-imidazol-3-ium bromide 在 三乙胺 、 六氟磷酸钾 作用下， 以 二氯甲烷 、 甲醇 、 水 为溶剂， 反应 20.17h， 以67%的产率得到1-{5-[(3R,5S)-5-(bis(3.5-dimethylphenyl)(trimethylsilyloxy)methyl)pyrrolidin-3-yloxy]-5-oxopentyl}-3-methyl-1H-imidazol-3-ium hexafluorophosphate
  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：

  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 在 5% Pd(II)/C(eggshell) 、 氢气 作用下， 以 甲醇 为溶剂， 以100%的产率得到1-{5-[(3R,5S)-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