(S)-(-)-3-(tert-butylsulfinyl)quinoline

• 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)-(-)-3-(tert-butylsulfinyl)quinoline
• 英文别名: 3-[(S)-tert-butylsulfinyl]quinoline
• 化学式: C₁₃H₁₅NOS
• 分子量: 233.334
• InChiKey: YRTMGFVVFUDJLH-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴喹啉 、 (S)-(-)-叔丁基亚磺酸硫代叔丁酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以37%的产率得到(S)-(-)-3-(tert-butylsulfinyl)quinoline
  参考文献：
  名称：

  ortho-Metalation of Enantiopure Aromatic Sulfoxides and Stereocontrolled Addition to Imines

  摘要：

  Enantiopure aromatic (phenyl, naphthyl) and heteroaromatic (pyridyl, quinolyl, diazinyl) sulfoxides have been synthesized by reaction of (S)-tert-butyl tert-butanethiosulfinate with aryl- or heteroaryllithium derivatives. The ortho-directed metalation of the sulfoxides was performed with lithium bases. Subsequent addition of the lithiated intermediates to N-tosylimines afforded tosylaminoalkyl tert-butylsulfinyl arenes. In most cases a complete asymmetric induction was highlighted in favor of (S,S) isomers. Heating the aminosulfoxides provided an original cyclization to form novel cyclic sulfenamides. A novel enantiopure synthesis of a benzylamine was described. An application of an enantiopure aminosulfoxide as N,S ligand for the asymmetric catalysis of allylic nucleophilic substitution has been successfully tested.

  DOI：

  10.1021/jo052358p

文献信息

• <i>ortho</i>-Metalation of Enantiopure Aromatic Sulfoxides and Stereocontrolled Addition to Imines
  作者：Nicolas Le Fur、Ljubica Mojovic、Nelly Plé、Alain Turck、Vincent Reboul、Patrick Metzner

  DOI：10.1021/jo052358p

  日期：2006.3.31

  Enantiopure aromatic (phenyl, naphthyl) and heteroaromatic (pyridyl, quinolyl, diazinyl) sulfoxides have been synthesized by reaction of (S)-tert-butyl tert-butanethiosulfinate with aryl- or heteroaryllithium derivatives. The ortho-directed metalation of the sulfoxides was performed with lithium bases. Subsequent addition of the lithiated intermediates to N-tosylimines afforded tosylaminoalkyl tert-butylsulfinyl arenes. In most cases a complete asymmetric induction was highlighted in favor of (S,S) isomers. Heating the aminosulfoxides provided an original cyclization to form novel cyclic sulfenamides. A novel enantiopure synthesis of a benzylamine was described. An application of an enantiopure aminosulfoxide as N,S ligand for the asymmetric catalysis of allylic nucleophilic substitution has been successfully tested.