(2S,5S)-2-(3-fluorophenoxy)-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one

• 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: (2S,5S)-2-(3-fluorophenoxy)-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one
• 英文别名: (1S,3aS)-1-(3-fluorophenoxy)-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphole 1-oxide
• 化学式: C₁₁H₁₃FNO₃P
• 分子量: 257.201
• InChiKey: JIXSVEBKGNLTID-BTDLBPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2-(3-fluorophenoxy)-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以65%的产率得到(2R,5S)-2-(2-fluoro-6-hydroxyphenyl)-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one
  参考文献：
  名称：

  Chiral (o-Hydroxyaryl)oxazaphospholidine Oxides: A New Class of Bifunctional Catalysts in the Enantioselective Borane Reduction of Ketones

  摘要：

  The synthesis of a new class of bifunctional organophosphorus catalysts for the asymmetric borane reduction of prochiral ketones has been investigated. Keys to the architecture of effective catalysts are an oxazaphospholidine structural unit and a hydroxyaryl moiety. These (o-hydroxyary-1)oxazaphospholidine oxides have been successfully applied to the catalytic (2 mol-%) asymmetric borane reduction of numerous prochiral ketones with enantiomeric excesses up to 84% ee.

  DOI：

  10.1002/1099-0690(200010)2000:19<3313::aid-ejoc3313>3.0.co;2-m
• 作为产物：
  描述：

  3-氟苯酚 、 (S)-吡咯烷-2-基甲醇 在 三(二甲胺基)膦 、 叔丁基过氧化氢 作用下， 以 甲苯 、 癸烷 、 二氯甲烷 为溶剂， 反应 7.0h， 以62%的产率得到(2S,5S)-2-(3-fluorophenoxy)-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one
  参考文献：
  名称：

  Chiral (o-Hydroxyaryl)oxazaphospholidine Oxides: A New Class of Bifunctional Catalysts in the Enantioselective Borane Reduction of Ketones

  摘要：

  The synthesis of a new class of bifunctional organophosphorus catalysts for the asymmetric borane reduction of prochiral ketones has been investigated. Keys to the architecture of effective catalysts are an oxazaphospholidine structural unit and a hydroxyaryl moiety. These (o-hydroxyary-1)oxazaphospholidine oxides have been successfully applied to the catalytic (2 mol-%) asymmetric borane reduction of numerous prochiral ketones with enantiomeric excesses up to 84% ee.

  DOI：

  10.1002/1099-0690(200010)2000:19<3313::aid-ejoc3313>3.0.co;2-m

文献信息

• Chiral (o-Hydroxyaryl)oxazaphospholidine Oxides: A New Class of Bifunctional Catalysts in the Enantioselective Borane Reduction of Ketones
  作者：Jean Michel Brunel、Olivier Legrand、Gérard Buono

  DOI：10.1002/1099-0690(200010)2000:19<3313::aid-ejoc3313>3.0.co;2-m

  日期：2000.10

  The synthesis of a new class of bifunctional organophosphorus catalysts for the asymmetric borane reduction of prochiral ketones has been investigated. Keys to the architecture of effective catalysts are an oxazaphospholidine structural unit and a hydroxyaryl moiety. These (o-hydroxyary-1)oxazaphospholidine oxides have been successfully applied to the catalytic (2 mol-%) asymmetric borane reduction of numerous prochiral ketones with enantiomeric excesses up to 84% ee.