(2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoic acid | 34882-18-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoic acid
• CAS: 34882-18-3；53530-49-7；63031-51-6；99094-07-2；130853-41-7；130853-42-8
• 化学式: C₉H₉BrO₃
• 分子量: 245.073
• InChiKey: PNZTVDQYHQRHKB-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoic acid 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 26.0h， 生成 methyl (2R,3R)-3-phenylglycidate
  参考文献：
  名称：

  Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones

  摘要：

  Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric alpha-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good. The ephedrine based aldol adducts were hydrolyzed to afford the alpha-bromo-beta-hydroxycarboxylic acids. The absolute stereochemistry and enantiomeric purity of these products were determined by chiral HPLC and specific rotation measurements. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.036
• 作为产物：
  描述：

  苯甲醛 在 硫酸 、 四氯化钛 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 26.0h， 生成 (2S,3R)-2-bromo-3-hydroxy-3-phenylpropanoic acid
  参考文献：
  名称：

  Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones

  摘要：

  Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric alpha-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good. The ephedrine based aldol adducts were hydrolyzed to afford the alpha-bromo-beta-hydroxycarboxylic acids. The absolute stereochemistry and enantiomeric purity of these products were determined by chiral HPLC and specific rotation measurements. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.06.036

文献信息

• Towards the development of oxadiazinanones as chiral auxiliaries: synthesis and application of N3-haloacetyloxadiazinanones
  作者：Trisha R. Hoover、Jonathan A. Groeper、Raleigh W. Parrott、Seshanand P. Chandrashekar、Jennifer M. Finefield、Alexandro Dominguez、Shawn R. Hitchcock

  DOI：10.1016/j.tetasy.2006.06.036

  日期：2006.7

  Oxadiazinanones derived from (1R,2S)-ephedrine and (1R,2S)-norephedrine were employed in the asymmetric alpha-halo aldol reaction. The optimized yields and diastereoselectivities for the ephedrine based oxadiazinanone aldol reaction ranged from fair to good. The ephedrine based aldol adducts were hydrolyzed to afford the alpha-bromo-beta-hydroxycarboxylic acids. The absolute stereochemistry and enantiomeric purity of these products were determined by chiral HPLC and specific rotation measurements. (c) 2006 Elsevier Ltd. All rights reserved.