[(R,R)-2-(2-diphenylphosphinophenyl)-5-methyl-4,5-dihydrooxazol-4-yl]methanol

• 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,R)-2-(2-diphenylphosphinophenyl)-5-methyl-4,5-dihydrooxazol-4-yl]methanol
• 英文别名: [(4R,5R)-2-(2-diphenylphosphanylphenyl)-5-methyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
• 化学式: C₂₃H₂₂NO₂P
• 分子量: 375.407
• InChiKey: PFMJAVYMBRVKID-DYESRHJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氟苯腈 在 正丁基锂 、 cadmium(II) acetate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯苯 为溶剂， 反应 17.0h， 生成 [(R,R)-2-(2-diphenylphosphinophenyl)-5-methyl-4,5-dihydrooxazol-4-yl]methanol
  参考文献：
  名称：

  Conformational Preferences and Enantiodiscrimination of Phosphino-4-(1-hydroxyalkyl)oxazoline−Metal−Olefin Complexes Resulting from an OH−Metal Hydrogen Bond

  摘要：

  Phosphinooxazolines carrying (1-hydroxy-1-phenyl)methyl and (1-methoxy-1-phenyl)methyl substituents in the 4 position of the oxazoline ring exhibit contrasting behavior in Pd-and Ir-catalyzed allylic alkylations. Whereas catalysts with the methoxy-containing ligand generally provide products with high ee's, use of catalysts prepared from the hydroxy-containing ligand results in products with low ee's or even racemates. DFT calculations suggest the presence of a hydrogen bond with Pd(0) as the proton acceptor in the hydroxy-containing olefin-Pd(0) complexes, which induces a conformational change in the ligand, leading to different stereoselectivity.

  DOI：

  10.1021/jo051610q

文献信息

• Conformational Preferences and Enantiodiscrimination of Phosphino-4-(1-hydroxyalkyl)oxazoline−Metal−Olefin Complexes Resulting from an OH−Metal Hydrogen Bond
  作者：Anders Frölander、Serghey Lutsenko、Timofei Privalov、Christina Moberg

  DOI：10.1021/jo051610q

  日期：2005.11.1

  Phosphinooxazolines carrying (1-hydroxy-1-phenyl)methyl and (1-methoxy-1-phenyl)methyl substituents in the 4 position of the oxazoline ring exhibit contrasting behavior in Pd-and Ir-catalyzed allylic alkylations. Whereas catalysts with the methoxy-containing ligand generally provide products with high ee's, use of catalysts prepared from the hydroxy-containing ligand results in products with low ee's or even racemates. DFT calculations suggest the presence of a hydrogen bond with Pd(0) as the proton acceptor in the hydroxy-containing olefin-Pd(0) complexes, which induces a conformational change in the ligand, leading to different stereoselectivity.