(2ambo,5S)-2-phenoxy-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one | 188755-65-9

• 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: (2ambo,5S)-2-phenoxy-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one
• 英文别名: (3aS)-1-phenoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaphosphole 1-oxide
• CAS: 188755-65-9
• 化学式: C₁₁H₁₄NO₃P
• 分子量: 239.211
• InChiKey: UNCRZCCGENEKMH-VQVVDHBBSA-N

物化性质

• 沸点：
  324.4±25.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (2ambo,5S)-2-phenoxy-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one 、 lithium diisopropyl amide 以 四氢呋喃 为溶剂， 反应 0.75h， 以12%的产率得到(2S,5S)-2-(2-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：

  L-脯氨酸 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 3.0h， 生成 (2ambo,5S)-2-phenoxy-1-aza-3-oxa-2-phosphabicyclo[3.3.0]octan-2-one
  参考文献：
  名称：

  STUDIES ON CHIRAL THIOPHOSPHORIC ACIDS AND THEIR DERIV ATIVES 16.-THE ASYMMETRIC CYCLIZATION OF L-(+)- PROLINOL WITH (THIO)PHOSPHORO(-NO)DICHLORIDATES

  摘要：

  The cyclizations of L-(+)-prolinol 5 with (thio)phosphoro(-no)dichloridates 6 give 1,2,3-azaphosphaoxabicyclo[3.3.0]octanes 7 consisting of unequal amounts of diastereoisomers, eight pairs of which have been successfully resolved by silica gel column chromatography or recrystallization. The influences of reaction temperature, solvent and substrate concentration upon the asymmetric induction have also been investigated.

  DOI：

  10.1080/10426509708040496

文献信息

• Synthesis of chiral phosphorus reagents and their catalytic activity in asymmetric borane reduction ofN-phenyl imine of acetophenone
  作者：Li Kangying、Zhou Zhenghong、Zhao Guofeng、Tang Chuchi

  DOI：10.1002/hc.10190

  日期：——

  Eleven chiral trivalent or quatrivalent phosphorus reagents were synthesized starting from L-proline, D-camphor, (+)- or (−)-1,1′-binaphthalene-2,2′-diol, (−)-α-phenylethylamine, etc. and their application as catalysts in asymmetric borane reduction of N-phenyl imine of acetophenone was preliminarily investigated. N-Phenyl α-phenylethylamine was obtained in good yield with low to moderate enantioselectivity

  以 L-脯氨酸、D-樟脑、(+)- 或 (-)-1,1'-联萘-2,2'-二醇、(-)-α-苯乙胺为原料合成了 11 种手性三价或四价磷试剂，初步研究了它们作为催化剂在苯乙酮N-苯基亚胺不对称硼烷还原反应中的应用。N-苯基α-苯乙胺以良好的收率获得，具有低至中等的对映选择性。© 2003 Wiley Periodicals, Inc. 杂原子化学 14:546–550, 2003; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10190
• STUDIES ON CHIRAL THIOPHOSPHORIC ACIDS AND THEIR DERIV ATIVES 16.-THE ASYMMETRIC CYCLIZATION OF L-(+)- PROLINOL WITH (THIO)PHOSPHORO(-NO)DICHLORIDATES
  作者：Zheng-Jie He、You-Ming Wang、Chu-Chi Tang

  DOI：10.1080/10426509708040496

  日期：1997.8.1

  The cyclizations of L-(+)-prolinol 5 with (thio)phosphoro(-no)dichloridates 6 give 1,2,3-azaphosphaoxabicyclo[3.3.0]octanes 7 consisting of unequal amounts of diastereoisomers, eight pairs of which have been successfully resolved by silica gel column chromatography or recrystallization. The influences of reaction temperature, solvent and substrate concentration upon the asymmetric induction have also been investigated.
• 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.