[(R,R)-2-(2-fluorophenyl)-5-methyl-4,5-dihydrooxazol-4-yl]methanol | 872052-25-0

• 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-fluorophenyl)-5-methyl-4,5-dihydrooxazol-4-yl]methanol
• 英文别名: [(4R,5R)-2-(2-fluorophenyl)-5-methyl-4,5-dihydro-1,3-oxazol-4-yl]methanol
• CAS: 872052-25-0
• 化学式: C₁₁H₁₂FNO₂
• 分子量: 209.22
• InChiKey: MGZMTFATBYHDSA-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(R,R)-2-(2-fluorophenyl)-5-methyl-4,5-dihydrooxazol-4-yl]methanol 在 正丁基锂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 (R,R)-2-(2-diphenylphosphinophenyl)-5-methyl-4-(tetrahydropyran-2-yloxymethyl)-4,5-dihydrooxazole
  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
• 作为产物：
  描述：

  2-氟苯腈 、 L-苏氨醇 在 cadmium(II) acetate 作用下， 以 氯苯 为溶剂， 反应 16.0h， 以28%的产率得到[(R,R)-2-(2-fluorophenyl)-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.