(2S,4S,5R)-2-(5-bromo-2-hydroxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2S,4S,5R)-2-(5-bromo-2-hydroxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine
• 英文别名: 4-bromo-2-((2S,4S,5R)-3,4-dimethyl-5-phenyloxazolidyn-2-yl)phenol；4-bromo-2-[(2S,4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl]phenol
• 化学式: C₁₇H₁₈BrNO₂
• 分子量: 348.239
• InChiKey: USLVDHPPHHAWNG-GOPGUHFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  麻黄碱 、 5-溴水杨醛 以 苯 为溶剂， 反应 2.0h， 以82.5%的产率得到(2S,4S,5R)-2-(5-bromo-2-hydroxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidine
  参考文献：
  名称：

  Synthesis and crystal structure of (2S,4S,5R)-2-(5-bromo-2-hydroxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidines

  摘要：

  Condensation of ephedrine alkaloids with 5-bromo-2-hydroxybenzaldehyde was studied, and X-ray diffraction analysis of the synthesized (2S,4S,5R)-2-(2-hydroxy-5-bromophenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidines was performed.

  DOI：

  10.1134/s1070363207090198

文献信息

• Synthesis and crystal structure of (2S,4S,5R)-2-(5-bromo-2-hydroxyphenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidines
  作者：O. A. Nurkenov、A. M. Gazaliev、D. M. Turdybekov、A. R. Dzhandigulov、S. M. Adekenov

  DOI：10.1134/s1070363207090198

  日期：2007.9

  Condensation of ephedrine alkaloids with 5-bromo-2-hydroxybenzaldehyde was studied, and X-ray diffraction analysis of the synthesized (2S,4S,5R)-2-(2-hydroxy-5-bromophenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidines was performed.
• Structural and electronic effects of oxazolidine ligands derived from (1R,2S)-ephedrine in the asymmetric addition of diethylzinc to aldehydes
  作者：Ewelina Błocka、Magdalena Jaworska、Anna Kozakiewicz、Mirosław Wełniak、Andrzej Wojtczak

  DOI：10.1016/j.tetasy.2010.02.029

  日期：2010.3

  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.