(3S,3aR,9bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methoxy-3a-trifluoromethyl-1,3,3a,4,5,9b-hexahydro-cyclopenta[a]naphthalen-2-one | 162788-79-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (3S,3aR,9bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methoxy-3a-trifluoromethyl-1,3,3a,4,5,9b-hexahydro-cyclopenta[a]naphthalen-2-one
• CAS: 162788-79-6
• 化学式: C₂₂H₃₁F₃O₃Si
• 分子量: 428.567
• InChiKey: MEWHWMLKPSEHRQ-LVCYWYKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.88
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,3aR,9bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methoxy-3a-trifluoromethyl-1,3,3a,4,5,9b-hexahydro-cyclopenta[a]naphthalen-2-one 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以66%的产率得到(3aS,9bS)-cis-3a,4,5,9b-Tetrahydro-2-methylene-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalen-2-one
  参考文献：
  名称：

  A Rapid Access to Both Enantiomers of 1,2,3,4-Tetranor B-Trienic 18,18,18-Trifluorosteroids. The First Enantiocontrolled Total Synthesis of 18,18,18-Trifluorosteroids

  摘要：

  Chiral A-tetranor B-trienic 18,18,18-trifluorosteroid 2a and its enantiomer 1a were synthesised by the thermolysis of chiral olefinic benzocyclobutenes 7b and 7a which were in turn prepared by the aldol reaction of chiral oxazolidinone 5 and 11 with 2-(4-methoxybenzocyclobutenyl-1)-acetaldehyde as a key step. The compound 1a was then transformed into 18,18,18-trifluorosteroid 9 via the ketone 13 and the diketone 14.

  DOI：

  10.1021/jo00108a022
• 作为产物：
  描述：

  (2S,3S,3aS,9bS)-cis-3-<<(tert-Butyldimethylsilyl)oxy>methyl>-2,3,3a,4,5,9b-hexahydro-2-hydroxy-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene 在 4 A molecular sieve 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以88%的产率得到(3S,3aR,9bR)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methoxy-3a-trifluoromethyl-1,3,3a,4,5,9b-hexahydro-cyclopenta[a]naphthalen-2-one
  参考文献：
  名称：

  A Rapid Access to Both Enantiomers of 1,2,3,4-Tetranor B-Trienic 18,18,18-Trifluorosteroids. The First Enantiocontrolled Total Synthesis of 18,18,18-Trifluorosteroids

  摘要：

  Chiral A-tetranor B-trienic 18,18,18-trifluorosteroid 2a and its enantiomer 1a were synthesised by the thermolysis of chiral olefinic benzocyclobutenes 7b and 7a which were in turn prepared by the aldol reaction of chiral oxazolidinone 5 and 11 with 2-(4-methoxybenzocyclobutenyl-1)-acetaldehyde as a key step. The compound 1a was then transformed into 18,18,18-trifluorosteroid 9 via the ketone 13 and the diketone 14.

  DOI：

  10.1021/jo00108a022