(2R)-2-[[(2S)-2-hydroxy-2-phenylacetyl]amino]propanoic acid | 127984-19-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2R)-2-[[(2S)-2-hydroxy-2-phenylacetyl]amino]propanoic acid
• CAS: 127984-19-4
• 化学式: C₁₁H₁₃NO₄
• 分子量: 223.229
• InChiKey: ZMKSFSXGEGKOSB-APPZFPTMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  PhCOCO-(R)-Ala-OH 在 RH(I)-Cy-POP-Ae (Rh+) 氢气 作用下， 以 甲醇 为溶剂， 以12%的产率得到(2R)-2-[[(2S)-2-hydroxy-2-phenylacetyl]amino]propanoic acid
  参考文献：
  名称：

  α-酮酸衍生物与 Rh(I)-手性二亚膦酸盐体系的不对称氢化。卤化物反离子对不对称感应的影响

  摘要：

  具有二环己基膦氧基和二甲氨基部分的手性二次膦酸配体 (Cy-POP-AE) 可在温和条件下通过 Rh(I) 催化剂有效地对 N-(苯甲酰基甲酰基) 氨基酸进行不对称氢化。中性铑 (I) 前体在甲醇中实现双重不对称诱导，而阳离子前体导致主要由底物手性控制的不对称诱导。

  DOI：

  10.1246/bcsj.63.281

文献信息

• Stereochemical effects in mass spectrometry. 7. Determination of absolute configuration of some organic molecules by reaction mass spectrometry
  作者：Yao-Zu Chen、Hung Li、Hou-Jun Yang、Su-Ming Hua、Hai-Quan Li、Fan-Zhi Zhao、Nen-Yu Chen

  DOI：10.1002/oms.1210231205

  日期：1988.12

  AbstractIt was found that in the chemical ionization (isobutane) mass spectra of some asymmetric secondary alcohols and α‐amino acids, when a pair of enantiomers (such as R‐ and S‐2‐phenyIbutyric anhydride, R‐ and S‐mandelic acid, R‐ and S‐2‐methylbutanoic acid or R‐ and S‐α‐phenyl ethyl amine) were used as reaction reagents, the relative abundances of characteristic ions formed by the stereoselective reaction between sample and reagent of the same configuration were much higher than those ions formed by the sample and a reagent of a different configuration. The absolute configuration of the sample molecule may be predicted by examination of mass spectra of the sample measured with R‐ and S‐reagent respectively. This approach proved to be a convenient way for determination of the absolute configurations of organic molecules on a micromole level by mass Spectrometry.