(2R)-2-hydroxy-(1S)-{[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-propyl}-carbamic acid benzyl ester | 1280627-21-5

• 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: (2R)-2-hydroxy-(1S)-{[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-propyl}-carbamic acid benzyl ester
• CAS: 1280627-21-5
• 化学式: C₂₉H₃₄N₂O₅
• 分子量: 490.599
• InChiKey: GUPXOWYKHYOUDZ-NYMACZPPSA-N

物化性质

• 熔点：
  120-122 °C
• 沸点：
  744.4±60.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.74
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107.89
• 氢给体数：
  4.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2R)-2-hydroxy-(1S)-{[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-propyl}-carbamic acid benzyl ester 在 六氟磷酸钾 、 4-二甲氨基吡啶 、 5% Pd(II)/C(eggshell) 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 5.0~80.0 ℃ 、100.0 kPa 条件下， 反应 14.08h， 生成 1-(4-{(2S)-2-amino-2-[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-(R)-1-methyl-ethoxycarbonyl}-butyl)-3-methyl-3H-imidazol-1-ium hexafluorophosphates
  参考文献：
  名称：

  (S)-Threonine/α,α-(S)-diphenylvalinol-derived chiral ionic liquid: an immobilized organocatalyst for asymmetric syn-aldol reactions

  摘要：

  Chiral ionic liquids containing (S)- or (R)-threonine amide and alpha,alpha-(S)-diphenylvalinol units were synthesized In the presence of the (S)-threonine-derived catalyst reactions between ketones with secondary carbon atom(s) at the alpha-position with respect to the carbonyl group and aromatic (heteroaromatic) aldehydes afforded the corresponding syn-aldols in high yields (up to 99%) and with high diastereo-(syn/anti up to 97:3) and enantioselectivity (up to 99% ee), which was maintained over three reaction cycles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.017
• 作为产物：
  描述：

  (S)-(-)-2-氨基-3-甲基-1,1-二苯基-1-丁醇 、 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 17.25h， 以5.4 g的产率得到(2R)-2-hydroxy-(1S)-{[(S)-1-(hydroxy-diphenyl-methyl)-2-methyl-propylcarbamoyl]-propyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  (S)-Threonine/α,α-(S)-diphenylvalinol-derived chiral ionic liquid: an immobilized organocatalyst for asymmetric syn-aldol reactions

  摘要：

  Chiral ionic liquids containing (S)- or (R)-threonine amide and alpha,alpha-(S)-diphenylvalinol units were synthesized In the presence of the (S)-threonine-derived catalyst reactions between ketones with secondary carbon atom(s) at the alpha-position with respect to the carbonyl group and aromatic (heteroaromatic) aldehydes afforded the corresponding syn-aldols in high yields (up to 99%) and with high diastereo-(syn/anti up to 97:3) and enantioselectivity (up to 99% ee), which was maintained over three reaction cycles. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.01.017