(1S,5S,7S)-4-Fluoro-6,6-dimethoxy-10,10-dimethyl-3-thia-4-aza-tricyclo[5.2.1.0^1,5]decane 3,3-dioxide

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,5S,7S)-4-Fluoro-6,6-dimethoxy-10,10-dimethyl-3-thia-4-aza-tricyclo[5.2.1.0^1,5]decane 3,3-dioxide
• 英文别名: (1S,5S,7S)-4-fluoro-6,6-dimethoxy-10,10-dimethyl-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide；(1S,5S,7S)-4-fluoro-6,6-dimethoxy-10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
• 化学式: C₁₂H₂₀FNO₄S
• 分子量: 293.36
• InChiKey: ARFLRBZGYZMDJH-ATZCPNFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (1S,5S,7S)-6,6-Dimethoxy-10,10-dimethyl-3-thia-4-aza-tricyclo[5.2.1.0^1,5]decane 3,3-dioxide 在 fluorine 、 sodium fluoride 作用下， 以 氯仿 为溶剂， 反应 1.5h， 以34%的产率得到(1S,5S,7S)-4-Fluoro-6,6-dimethoxy-10,10-dimethyl-3-thia-4-aza-tricyclo[5.2.1.0^1,5]decane 3,3-dioxide
  参考文献：
  名称：

  Asymmetric Fluorination of Enolates with Nonracemic N-Fluoro-2,10-Camphorsultams

  摘要：

  The asymmetric "electrophilic" fluorination of tertiary enolates by nonracemic N-fluoro-2,10-camphorsultams 3 affords quaternary alpha-fluoro carbonyl compounds in modest yield and ee. The highest asymmetric induction was observed for the fluorination of the sodium enolate of 2-methyl-1-tetralone (8a) by (-)-N-fluoro-2,10-(3,3-dichlorocamphorsultam) (3b) to give (S)-(+)-2-fluoro-2-methyl-1-tetralone (9a) in 70% ee. The absolute configuration was established by X-ray crystallography of the corresponding diastereomeric beta-hydroxy sulfoximine prepared from (+/-)-9a and the Johnson reagent. The asymmetric induction exhibited by 3 is opposite to that of the closely related enolate hydroxylation reagents nonracemic (camphorylsulfonyl)oxaziridines 4. The N-fluoro sultams 3 were prepared by fluorination (10% F-2/N-2) of the corresponding sultams 5.

  DOI：

  10.1021/jo972045x

文献信息

• Asymmetric Fluorination of Enolates with Nonracemic <i>N</i>-Fluoro-2,10-Camphorsultams
  作者：Franklin A. Davis、Ping Zhou、Christopher K. Murphy、Gajendran Sundarababu、Hongyan Qi、Wei Han、Robert M. Przeslawski、Bang-Chi Chen、Patrick J. Carroll

  DOI：10.1021/jo972045x

  日期：1998.4.1

  The asymmetric "electrophilic" fluorination of tertiary enolates by nonracemic N-fluoro-2,10-camphorsultams 3 affords quaternary alpha-fluoro carbonyl compounds in modest yield and ee. The highest asymmetric induction was observed for the fluorination of the sodium enolate of 2-methyl-1-tetralone (8a) by (-)-N-fluoro-2,10-(3,3-dichlorocamphorsultam) (3b) to give (S)-(+)-2-fluoro-2-methyl-1-tetralone (9a) in 70% ee. The absolute configuration was established by X-ray crystallography of the corresponding diastereomeric beta-hydroxy sulfoximine prepared from (+/-)-9a and the Johnson reagent. The asymmetric induction exhibited by 3 is opposite to that of the closely related enolate hydroxylation reagents nonracemic (camphorylsulfonyl)oxaziridines 4. The N-fluoro sultams 3 were prepared by fluorination (10% F-2/N-2) of the corresponding sultams 5.