4,5-dimethyl-2-(1,1,2,2-tetrafluoroethyl)-2-{[(1S)-endo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]oxy}-3,6-dihydro-2H-thiopyran | 1240463-75-5

• 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: 4,5-dimethyl-2-(1,1,2,2-tetrafluoroethyl)-2-{[(1S)-endo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]oxy}-3,6-dihydro-2H-thiopyran
• CAS: 1240463-75-5
• 化学式: C₁₉H₂₈F₄OS
• 分子量: 380.49
• InChiKey: MALJPUCWYFKMHK-MJKDJBKUSA-N

反应信息

• 作为产物：
  描述：

  O-[(1S)-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]-2,2,3,3-tetrafluoropropanethioate 、 2,3-二甲基-1,3-丁二烯 以 苯 为溶剂， 反应 5.0h， 以75%的产率得到4,5-dimethyl-2-(1,1,2,2-tetrafluoroethyl)-2-{[(1S)-endo-1,7,7-trimethylbicyclo[2.2.1]hept-2-yl]oxy}-3,6-dihydro-2H-thiopyran
  参考文献：
  名称：

  Asymmetric induction in thia-Diels-Alder reactions of chiral polyfluoroalkylthionocarboxylates

  摘要：

  A series of chiral S- or O-alkyl thionoesters have been synthesized by treatment of trifluorothioacetyl- or 2,2,3,3-tetrafluorothiopropionyl chloride with corresponding thiols or alcohols. The thia-Diels-Alder reaction of the thionoesters with symmetrical 1,3-dienes proceeds with diastereoselectivity up to 60%. Structures of cycloaddition products and corresponding transition states have been studied at the DFT level of approximation. The experimentally observed diastereomeric excess has been referred to differences in activation energies of transition states, preceding formation of the diastereomeric cycloaducts. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.11.011