(+/-)-(2R,3S)-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: (+/-)-(2R,3S)-2-bromo-3-hydroxy-3-phenylpropanoic acid
• 英文别名: (+/-)-2r_F-bromo-3t_F-hydroxy-3cat_F-phenyl-propionic acid；(+/-)-2r_F-Brom-3t_F-hydroxy-3cat_F-phenyl-propionsaeure；rac.threo-2-Brom-3-hydroxy-3-phenylpropionsaeure；(2R,3S)-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-SFYZADRCSA-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：

  (+/-)-(2R,3S)-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 22.0h， 生成 顺-(2S,3S)甲基环氧肉桂酸酯
  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：

  別桂皮酸 在 sodium hypobromide 、 potassium carbonate 作用下， 生成 (+/-)-(2R,3S)-2-bromo-3-hydroxy-3-phenylpropanoic acid
  参考文献：
  名称：

  Berner; Riiber, Chemische Berichte, 1921, vol. 54, p. 1957

  摘要：

  DOI：

文献信息

• Asymmetric bromination-aldolization of chiral acetate titanium enolate derived from thioimide. A general approach to the synthesis of enantiopure α-bromo-β-hydroxy carboxylic acids
  作者：Ying-Chuan Wang、Dah-Wei Su、Chen-Men Lin、Hsi-Liang Tseng、Chi-Lung Li、Tu-Hsin Yan

  DOI：10.1016/s0040-4039(99)00576-6

  日期：1999.4

  Chiral acetate titanium enolate derived from thioimide efficiently effects one-step bromination-aldolization with excellent yields and exceptionally high levels of asymmetric induction in aldol additions. General base promoted oxazolidinethione deacylation provides direct access to chiral α-bromo-β-hydroxy acids.

  衍生自硫酰亚胺的手性乙酸烯醇钛酸酯可有效完成一步溴化-醛缩醛化反应，并具有优异的收率，并且在添加醛醇缩合剂时异常高的不对称诱导率。一般的碱促进的恶唑烷硫酮脱酰作用可直接获得手性α-溴-β-羟基酸。
• Berner; Riiber, Chemische Berichte, 1921, vol. 54, p. 1957
  作者：Berner、Riiber

  DOI：——

  日期：——
• 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.