(4S,5R)-3,4-dimethyl-2-(2-naphthyl)-5-phenyloxazolidine | 103721-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4S,5R)-3,4-dimethyl-2-(2-naphthyl)-5-phenyloxazolidine
• CAS: 103721-34-2
• 化学式: C₂₁H₂₁NO
• 分子量: 303.404
• InChiKey: RXBBBSGVDLPKNG-JHVJFLLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  12.47
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4S,5R)-3,4-dimethyl-2-(2-naphthyl)-5-phenyloxazolidine 在 lithium aluminium tetrahydride 、 水 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以77%的产率得到(1R,2S)-2-((2-naphthylmethyl)(methyl)amino)-1-phenyl-1-propanol
  参考文献：
  名称：

  Aromatic motifs in the design of Ephedra ligands for application in the asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines

  摘要：

  Using N-benzylephedrine as a model, a collection of N-arylmethylephedrine derivatives has been prepared. These derivatives were prepared by treatment of ephedrine with selected aldehydes to create oxazolidines 8a-e. Reduction of the oxazolidines with lithium aluminum hydride afforded the target beta-amino alcohols 9a-e. When applied in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines, the derivatives yielded product enantioselectivities that were comparable to those of N-benzylephedrine. An N-cyclohexylmethylephedrine derivative was also prepared: this 13-aminoalcohol did not perform well in the catalytic addition of diethylzinc to 2-naphthaldehyde, thus suggesting that the aromatic motif is important in terms of maintaining a reasonable level of asymmetric induction. Finally, N-benzyl-N-methyl-2-amino-1,2-diphenyl-1-ethanol, an analogue of the N-benzylephedrine derivative, was prepared. This compound yielded comparable enantioselectivities in the catalytic asymmetric addition when employed as a ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.026
• 作为产物：
  描述：

  麻黄碱 、 2-萘甲醛 在 magnesium sulfate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以64%的产率得到(4S,5R)-3,4-dimethyl-2-(2-naphthyl)-5-phenyloxazolidine
  参考文献：
  名称：

  Aromatic motifs in the design of Ephedra ligands for application in the asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines

  摘要：

  Using N-benzylephedrine as a model, a collection of N-arylmethylephedrine derivatives has been prepared. These derivatives were prepared by treatment of ephedrine with selected aldehydes to create oxazolidines 8a-e. Reduction of the oxazolidines with lithium aluminum hydride afforded the target beta-amino alcohols 9a-e. When applied in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines, the derivatives yielded product enantioselectivities that were comparable to those of N-benzylephedrine. An N-cyclohexylmethylephedrine derivative was also prepared: this 13-aminoalcohol did not perform well in the catalytic addition of diethylzinc to 2-naphthaldehyde, thus suggesting that the aromatic motif is important in terms of maintaining a reasonable level of asymmetric induction. Finally, N-benzyl-N-methyl-2-amino-1,2-diphenyl-1-ethanol, an analogue of the N-benzylephedrine derivative, was prepared. This compound yielded comparable enantioselectivities in the catalytic asymmetric addition when employed as a ligand. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.026

文献信息

• Aromatic motifs in the design of Ephedra ligands for application in the asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines
  作者：Sucharita Banerjee、Anthony J. Camodeca、Gregory G. Griffin、Christopher G. Hamaker、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2010.02.026

  日期：2010.3

  Using N-benzylephedrine as a model, a collection of N-arylmethylephedrine derivatives has been prepared. These derivatives were prepared by treatment of ephedrine with selected aldehydes to create oxazolidines 8a-e. Reduction of the oxazolidines with lithium aluminum hydride afforded the target beta-amino alcohols 9a-e. When applied in the catalytic asymmetric addition of diethylzinc to aldehydes and diphenylphosphinoylimines, the derivatives yielded product enantioselectivities that were comparable to those of N-benzylephedrine. An N-cyclohexylmethylephedrine derivative was also prepared: this 13-aminoalcohol did not perform well in the catalytic addition of diethylzinc to 2-naphthaldehyde, thus suggesting that the aromatic motif is important in terms of maintaining a reasonable level of asymmetric induction. Finally, N-benzyl-N-methyl-2-amino-1,2-diphenyl-1-ethanol, an analogue of the N-benzylephedrine derivative, was prepared. This compound yielded comparable enantioselectivities in the catalytic asymmetric addition when employed as a ligand. (C) 2010 Elsevier Ltd. All rights reserved.