(2S,3S,3aR,9bS,1''R,2''S,5''R)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1',2-O-(2''-isopropyl-5''-methylcyclohexylidene)-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene

• 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,1''R,2''S,5''R)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1',2-O-(2''-isopropyl-5''-methylcyclohexylidene)-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene
• 英文别名: (2S,3S,3aR,9bS,1''R,2''S,5''R)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1',2-O-(2''-isopropyl-5''-methylcyclohexylidene)-7-methoxy-3a-(trifluoromethyl)-1H-yclopenta[a]naphthalene；(1R,2'S,5'R,10S,11S,14R,16S)-5-methoxy-5'-methyl-2'-propan-2-yl-10-(trifluoromethyl)spiro[13,15-dioxatetracyclo[8.7.0.02,7.011,16]heptadeca-2(7),3,5-triene-14,1'-cyclohexane]
• 化学式: C₂₆H₃₅F₃O₃
• 分子量: 452.557
• InChiKey: ODAMTBRMFYKEOP-SJBQZFOSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 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

• 作为产物：
  描述：

  (2S,3S,3aR,9bS)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-7-methoxy-3a-(trifluoromethyl)-1H-yclopentanaphthalene 在 三氟甲磺酸三甲基硅酯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 (2S,3S,3aR,9bS,1''R,2''S,5''R)-trans-2,3,3a,4,5,9b-Hexahydro-2-hydroxy-3-(hydroxymethyl)-1',2-O-(2''-isopropyl-5''-methylcyclohexylidene)-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.