(-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime) | 196409-10-6

• 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: (-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime)
• 英文别名: (1R,2E)-2-methoxyimino-1-phenylpropan-1-ol
• CAS: 196409-10-6
• 化学式: C₁₀H₁₃NO₂
• 分子量: 179.219
• InChiKey: XFCZXXPRDPDALH-NGPGYTDTSA-N

物化性质

• 沸点：
  283.1±50.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime) 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 去甲麻黄碱 、 L-(-)-去甲伪麻黄碱
  参考文献：
  名称：

  Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime). A key step for a (−)-norephedrine synthesis

  摘要：

  The enantioselective Baker's yeast reduction of (E)-1-phenyl-1,2 propanedione 2-(O-methyloxime) 1 afforded (-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime) 2 with 97% of enantiomeric excess (ee) which was diastereoselectively reduced by LiAlH4 to obtain the (-)-(R,S)-norephedrine with ee=82% and (-)-(R,R)-norpseudoephedrine with ee=93% in a ratio 4:1 respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00280-2
• 作为产物：
  描述：

  1-苯基-1,2-丙二酮 在 baker's yeast 、 Montmorillonite K₁₀ 、 potassium chloride 、 蔗糖 作用下， 反应 24.0h， 生成 (-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime)
  参考文献：
  名称：

  Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime). A key step for a (−)-norephedrine synthesis

  摘要：

  The enantioselective Baker's yeast reduction of (E)-1-phenyl-1,2 propanedione 2-(O-methyloxime) 1 afforded (-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime) 2 with 97% of enantiomeric excess (ee) which was diastereoselectively reduced by LiAlH4 to obtain the (-)-(R,S)-norephedrine with ee=82% and (-)-(R,R)-norpseudoephedrine with ee=93% in a ratio 4:1 respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00280-2

文献信息

• Enantioselective bioreduction of ( E )-1-phenyl-1,2-alkanedione 2-( O- methyloxime)
  作者：Olyr C Kreutz、Renata C.M Segura、J.Augusto R Rodrigues、Paulo J.S Moran

  DOI：10.1016/s0957-4166(00)00163-4

  日期：2000.6

  The baker's yeast reduction of (E)-1-phenyI-1,2-alkanedione 2-(O-methyloxime), PhC(O)C(NOMe)R (R = Me, Et, n-Pr, n-Bu), gave the corresponding optically active alcohols PhCH2OHC(NOMe)R in 88-99% enantiomeric excess and 48-75% chemical yield. The R configuration was proposed for these alcohols based on circular dichroism analysis. Only the phenylglyoxal O-methylaldoxime (R=H) gave poor enantiomeric excess (65%) and chemical yield (14%). These compounds are potential chiral building blocks for the stereoselective synthesis of norephedrine analogs. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime). A key step for a (−)-norephedrine synthesis
  作者：Olyr C. Kreutz、Paulo J.S. Moran、J.Augusto R. Rodrigues

  DOI：10.1016/s0957-4166(97)00280-2

  日期：1997.8

  The enantioselective Baker's yeast reduction of (E)-1-phenyl-1,2 propanedione 2-(O-methyloxime) 1 afforded (-)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime) 2 with 97% of enantiomeric excess (ee) which was diastereoselectively reduced by LiAlH4 to obtain the (-)-(R,S)-norephedrine with ee=82% and (-)-(R,R)-norpseudoephedrine with ee=93% in a ratio 4:1 respectively. (C) 1997 Elsevier Science Ltd.