(S)-(4-benzyl-2,2-dimethyloxazolidin-3-yl)quinolin-3-yl-methanone | 936347-53-4

• 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
• 英文名称: (S)-(4-benzyl-2,2-dimethyloxazolidin-3-yl)quinolin-3-yl-methanone
• 英文别名: [(4S)-4-benzyl-2,2-dimethyl-1,3-oxazolidin-3-yl]-quinolin-3-ylmethanone
• CAS: 936347-53-4
• 化学式: C₂₂H₂₂N₂O₂
• 分子量: 346.429
• InChiKey: VEIYFARGWYGQGZ-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(4-benzyl-2,2-dimethyloxazolidin-3-yl)quinolin-3-yl-methanone 、 烯丙基三丁基锡 、 氯甲酸甲酯 反应 21.0h， 生成 (4S,2'S)-2-allyl-3-(4-benzyl-2,2-dimethyl-oxazolidine-3-carbonyl)-2H-quinoline-1-carboxylic acid methyl ester 、 (4S,2'R)-2-allyl-3-(4-benzyl-2,2-dimethyl-oxazolidine-3-carbonyl)-2H-quinoline-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Regio- and Stereoselective Addition of Allylmetal Reagents to Pyridinium−π and Quinolinium−π Complexes

  摘要：

  Regio- and stereoselective allylation of pyridinium and quinolinium salts was performed by the addition of allylindium and allyltributyltin reagents toward intermediary cation-pi complexes. The reaction with allylindium and allyltributyltin reagents afforded a 1,2-adduct, whereas the addition of a prenylindium reagent gave a 1,4-adduct with good regio- and stereoselectivities. X-ray structural analysis, H-1 NMR studies, and DFT calculations elucidated the intermediary cation-pi complex formation with face-to-face orientation.

  DOI：

  10.1021/ol070168q
• 作为产物：
  描述：

  喹啉-3-羧酸 、 (4S)-2,2-dimethyl-4-phenylmethyloxazolidine 在 氯化亚砜 、 N,N-二甲基甲酰胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 34.0h， 以50%的产率得到(S)-(4-benzyl-2,2-dimethyloxazolidin-3-yl)quinolin-3-yl-methanone
  参考文献：
  名称：

  Regio- and Stereoselective Addition of Allylmetal Reagents to Pyridinium−π and Quinolinium−π Complexes

  摘要：

  Regio- and stereoselective allylation of pyridinium and quinolinium salts was performed by the addition of allylindium and allyltributyltin reagents toward intermediary cation-pi complexes. The reaction with allylindium and allyltributyltin reagents afforded a 1,2-adduct, whereas the addition of a prenylindium reagent gave a 1,4-adduct with good regio- and stereoselectivities. X-ray structural analysis, H-1 NMR studies, and DFT calculations elucidated the intermediary cation-pi complex formation with face-to-face orientation.

  DOI：

  10.1021/ol070168q