1-((2S,4S,5R)-3,4-dimethyl-5-phenyl-oxazolidyn-2-yl)naphthalen-2-ol | 1233691-19-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-((2S,4S,5R)-3,4-dimethyl-5-phenyl-oxazolidyn-2-yl)naphthalen-2-ol
• CAS: 1233691-19-4
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: VMFQIOVKAKKPCS-WVFSVQOHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.64
• 重原子数：
  24.0
• 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：
  32.7
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  麻黄碱 、 2-羟基-1-萘甲醛 以 乙醇 为溶剂， 反应 24.0h， 以45%的产率得到1-((2S,4S,5R)-3,4-dimethyl-5-phenyl-oxazolidyn-2-yl)naphthalen-2-ol
  参考文献：
  名称：

  Structural and electronic effects of oxazolidine ligands derived from (1R,2S)-ephedrine in the asymmetric addition of diethylzinc to aldehydes

  摘要：

  The purpose of this research was to determine the activity of chiral oxazolidine ligands prepared from (1R,2S)-ephedrine for the enantioselective addition of diethylzinc to aldehydes. The configuration on the newly formed C2 stereogenic center was determined as (2S) by X-ray structural analysis. Oxazolidine ligands reveal medium enantioselectivity with the ee exceeding 57%, and the yields obtained being 68-99%. The results indicate that the absolute configuration of the addition product depends not only on the N3-methyl as an important stereocontrol element but also on both the electronic and steric effects of the substrates and oxazolidine ligands. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.029
• 作为试剂：
  描述：

  diethylzinc 、 2-氯苯甲醛 在 1-((2S,4S,5R)-3,4-dimethyl-5-phenyl-oxazolidyn-2-yl)naphthalen-2-ol 作用下， 以 正己烷 、 甲苯 为溶剂， 反应 72.0h， 以73%的产率得到(R)-1-(2-chlorophenyl)propanol
  参考文献：
  名称：

  Structural and electronic effects of oxazolidine ligands derived from (1R,2S)-ephedrine in the asymmetric addition of diethylzinc to aldehydes

  摘要：

  The purpose of this research was to determine the activity of chiral oxazolidine ligands prepared from (1R,2S)-ephedrine for the enantioselective addition of diethylzinc to aldehydes. The configuration on the newly formed C2 stereogenic center was determined as (2S) by X-ray structural analysis. Oxazolidine ligands reveal medium enantioselectivity with the ee exceeding 57%, and the yields obtained being 68-99%. The results indicate that the absolute configuration of the addition product depends not only on the N3-methyl as an important stereocontrol element but also on both the electronic and steric effects of the substrates and oxazolidine ligands. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.02.029