| 1312798-39-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• CAS: 1312798-39-2
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: LVWKMWHGOIZHAP-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.95
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  在 Chiralpack AD 作用下， 以 邻二甲苯 为溶剂， 反应 24.0h， 生成 、
  参考文献：
  名称：

  Determination of the absolute configuration of the enantiomers of dihydroquinolines, isolated by chiral chromatography, by non empirical analysis of circular dichroism spectra and X-ray analysis

  摘要：

  The enantiomers of racemic 3,4-dihydroquinolines with an acetal or thioacetal Spiro ring and a quaternary stereogenic carbon have been isolated through semipreparative chiral chromatography using a polysaccharide-derived chiral stationary phase (Chiralpak AD) and n-hexane/ethanol as a mobile phase. The absolute configurations of the enantiomers of four compounds have been determined by a comparison of density functional theory (DFT) calculations of their electronic circular dichroism (ECD) spectra with the experimental ECD data. A detailed conformer population search to achieve a conformational average of these compounds was crucial, due to the flexibility of these molecules. The conformer distribution was evaluated by SPARTAN 02 and the structure of each of the conformers found within 4 kcal/mol energy range was optimized with DFT. The final calculated ECD spectrum obtained after Boltzmann averaging was compared with the ECD spectrum of the less well retained enantiomer and the correlation (R)/(-) was established for all compounds. The monocrystals of both enantiomers of one compound were obtained from the HPLC eluates. Their absolute configurations were determined by X-ray crystallographic analysis and confirmed by ECD analysis. In all cases, the second-eluted enantiomer in chiral HPLC exhibits an (R)-configuration. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.01.010

文献信息

• Determination of the absolute configuration of the enantiomers of dihydroquinolines, isolated by chiral chromatography, by non empirical analysis of circular dichroism spectra and X-ray analysis
  作者：Salvatore Caccamese、Giovanni Battista Barrano、Mateo Alajarin、Baltasar Bonillo、Ángel Vidal、Giuseppe Bruno、Giuseppe Mazzeo、Carlo Rosini

  DOI：10.1016/j.tetasy.2011.01.010

  日期：2011.2

  The enantiomers of racemic 3,4-dihydroquinolines with an acetal or thioacetal Spiro ring and a quaternary stereogenic carbon have been isolated through semipreparative chiral chromatography using a polysaccharide-derived chiral stationary phase (Chiralpak AD) and n-hexane/ethanol as a mobile phase. The absolute configurations of the enantiomers of four compounds have been determined by a comparison of density functional theory (DFT) calculations of their electronic circular dichroism (ECD) spectra with the experimental ECD data. A detailed conformer population search to achieve a conformational average of these compounds was crucial, due to the flexibility of these molecules. The conformer distribution was evaluated by SPARTAN 02 and the structure of each of the conformers found within 4 kcal/mol energy range was optimized with DFT. The final calculated ECD spectrum obtained after Boltzmann averaging was compared with the ECD spectrum of the less well retained enantiomer and the correlation (R)/(-) was established for all compounds. The monocrystals of both enantiomers of one compound were obtained from the HPLC eluates. Their absolute configurations were determined by X-ray crystallographic analysis and confirmed by ECD analysis. In all cases, the second-eluted enantiomer in chiral HPLC exhibits an (R)-configuration. (C) 2011 Elsevier Ltd. All rights reserved.