(2S,3S,3aR,9bS)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene | 162788-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: (2S,3S,3aR,9bS)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene
• 英文别名: (1R,10S,11S,16S)-5-methoxy-14,14-dimethyl-10-(trifluoromethyl)-13,15-dioxatetracyclo[8.7.0.02,7.011,16]heptadeca-2(7),3,5-triene
• CAS: 162788-70-7
• 化学式: C₁₉H₂₃F₃O₃
• 分子量: 356.385
• InChiKey: FEGAZKLSDWIYEA-CVYDXHPNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  6

上下游信息

反应信息

• 作为反应物：
  描述：

  (2S,3S,3aR,9bS)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene 在 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 生成 (2S,3S,3aR,9bS)-trans-2,3,3a,4,5,9b-Hexahydro-7-methoxy-3a-(trifluoromethyl)-2-<(trimethylsilyl)oxy>-3-<<(trimethylsilyl)oxy>methyl>-1H-yclopentanaphthalene
  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：

  (3-methoxybicyclo[4.2.0]octa-1,3,5-triene-7-yl)acetaldehyde 在 camphor-10-sulfonic acid 作用下， 以 二氯甲烷 、 邻二氯苯 为溶剂， 反应 10.0h， 生成 (2S,3S,3aR,9bS)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene
  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

文献信息

• 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
  作者：Hideo Nemoto、Atsushi Satoh、Keiichiro Fukumoto、Chizuko Kabuto

  DOI：10.1021/jo00108a022

  日期：1995.2

  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.