(4S)-3-(1-Oxo-2-phenylpropyl)-4-(1-methylethyl)oxazolidine-2-selone | 136794-59-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-3-(1-Oxo-2-phenylpropyl)-4-(1-methylethyl)oxazolidine-2-selone
• 英文别名: 2-phenyl-1-[(4S)-4-propan-2-yl-2-selanylidene-1,3-oxazolidin-3-yl]propan-1-one
• CAS: 136794-59-7；136794-66-6
• 化学式: C₁₅H₁₉NO₂Se
• 分子量: 324.281
• InChiKey: XMDGIMJGYPMSBA-GLGOKHISSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (S)-4-isopropyl-4,5-dihydrooxazole 在 selenium 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (4S)-3-(1-Oxo-2-phenylpropyl)-4-(1-methylethyl)oxazolidine-2-selone
  参考文献：
  名称：

  An improved synthesis of chiral oxazolidine-2-selones: highly sensitive selenium-77 NMR reagents for the detection and quantitation of chirality

  摘要：

  The synthesis of the title compounds from readily available oxazolines has been accomplished in one step in high yield. These chiral reagents exhibit extraordinary Se-77 chemical shift sensitivity and are useful for the detection and quantitation of chirality at remotely disposed chiral centers.

  DOI：

  10.1021/jo00024a003

文献信息

• Synthesis and Characterization of Acylated Chiral Oxazolidine-2-selones: Selone Chiral Derivatizing Agents for the Detection and Quantitation of Remotely Disposed Chiral Centers
  作者：Jie Peng、Mary E. Barr、David A. Ashburn、Lukasz Lebioda、Albert R. Garber、Rodolfo A. Martinez、Jerome D. Odom、R. Bruce Dunlap、Louis A. Silks

  DOI：10.1021/jo00122a039

  日期：1995.9

  Racemic and chiral carboxylic acids and acid chlorides are coupled cleanly to oxazolidine-2-selone chiral derivatizing agents (CDA's) with yields ranging from 85 to 99%. Se-77 NMR spectroscopy provides a highly sensitive method for the determination of the enantiomeric excesses of these remotely disposed chiral centers. The geometrical relationship between the selenocarbonyl and the adduct carbonyl (syn or anti) appears to have a profound effect on the chemical shift difference (Delta delta(Se)) observed for pairs of adduct diastereomers. Crystallographic and solution state NMR studies suggest that the syn orbital overlap enhances the Delta delta(Se).