(2R,3R,3aS,9bR)-trans-1,2,3,3a,4,5,6,8,9,9b-Decahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-3a-(trifluoromethyl)cyclopentanaphthalen-7-one | 162788-83-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R,3aS,9bR)-trans-1,2,3,3a,4,5,6,8,9,9b-Decahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-3a-(trifluoromethyl)cyclopentanaphthalen-7-one
• 英文别名: (1S,10R,11R,16R)-14,14-dimethyl-10-(trifluoromethyl)-13,15-dioxatetracyclo[8.7.0.02,7.011,16]heptadec-2(7)-en-5-one
• CAS: 162788-83-2
• 化学式: C₁₈H₂₃F₃O₃
• 分子量: 344.374
• InChiKey: HVMDRHNPKJGOOU-KLZNWCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  24.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (2R,3R,3aS,9bR)-trans-1,2,3,3a,4,5,6,8,9,9b-Decahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-3a-(trifluoromethyl)cyclopentanaphthalen-7-one 在 盐酸 、 对甲苯磺酸 、 potassium iodide 作用下， 以 苯 为溶剂， 反应 5.5h， 生成 (2R,3R,3aR,9aS,9bS)-6-((E)-3-Chloro-but-2-enyl)-2-hydroxy-3-hydroxymethyl-3a-trifluoromethyl-1,2,3,3a,4,5,8,9,9a,9b-decahydro-cyclopenta[a]naphthalen-7-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：

  (2R,3R)-4-(3-Methoxy-bicyclo[4.2.0]octa-1⁽⁶⁾,2,4-trien-7-yl)-2-(1-trifluoromethyl-vinyl)-butane-1,3-diol 在 camphor-10-sulfonic acid 、 氨 、 sodium 、 草酸 作用下， 以 二氯甲烷 、 邻二氯苯 为溶剂， 反应 32.33h， 生成 (2R,3R,3aS,9bR)-trans-1,2,3,3a,4,5,6,8,9,9b-Decahydro-2-hydroxy-3-(hydroxymethyl)-1'2-O-isopropylidene-3a-(trifluoromethyl)cyclopentanaphthalen-7-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

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.