2-[(2S,4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-[(2S,4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol
• 英文别名: ((2S,4S,5R)-3,4-dimethyl-5-phenyl-oxazolidyn-2-yl)phenol；2-[(2S,4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidin-2-yl]phenol
• 化学式: C₁₇H₁₉NO₂
• 分子量: 269.343
• InChiKey: BOKYNTRREGYZJE-ZLIFDBKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 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：

  邻甲基苄醇 、 麻黄碱 在 sodium sulfate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以55%的产率得到2-[(2S,4S,5R)-3,4-dimethyl-5-phenyloxazolidin-2-yl]phenol
  参考文献：
  名称：

  Intramolecular chiral relay at stereogenic nitrogen: oxazolidine catalysts derived from Ephedra alkaloids

  摘要：

  A series of oxazolidines have been prepared by reaction of either (1R,2S)-ephedrine or (1S,2S)-pseudoephedrine with salicylaldehyde derivatives. The resultant oxazolidines were used as catalytic ligands in the addition of diethylzinc to a variety of aromatic and aliphatic aldehydes. It was determined that the (1R,2S)-ephedrine based oxazolidine derivative 9 gave the highest enantioselectivities. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.12.029

文献信息

• 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.
• Bourne, Susan A.; Fitz, Lawrence D.; Kashyap, Ram P., Journal of Chemical Crystallography, 1997, vol. 27, # 1, p. 35 - 44
  作者：Bourne, Susan A.、Fitz, Lawrence D.、Kashyap, Ram P.、Krawiec, Mariusz、Walker, Richard B.、Watson, William H.、Williams, Lance M.

  DOI：——

  日期：——
• Intramolecular chiral relay at stereogenic nitrogen: oxazolidine catalysts derived from Ephedra alkaloids
  作者：Raleigh W. Parrott、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2006.12.029

  日期：2007.2

  A series of oxazolidines have been prepared by reaction of either (1R,2S)-ephedrine or (1S,2S)-pseudoephedrine with salicylaldehyde derivatives. The resultant oxazolidines were used as catalytic ligands in the addition of diethylzinc to a variety of aromatic and aliphatic aldehydes. It was determined that the (1R,2S)-ephedrine based oxazolidine derivative 9 gave the highest enantioselectivities. (c) 2007 Elsevier Ltd. All rights reserved.