(8R,9S,13S,14S,16S,17S)-16-(hydroxymethyl)-3-methoxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopenta[a]phenanthren-17(6H)-ol | 158498-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (8R,9S,13S,14S,16S,17S)-16-(hydroxymethyl)-3-methoxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopenta[a]phenanthren-17(6H)-ol
• CAS: 158498-11-4
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: TYPXYBMZQWSCFK-ZCHQJCHRSA-N

物化性质

• 沸点：
  508.7±50.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,16S,17S)-16-(hydroxymethyl)-3-methoxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopenta[a]phenanthren-17(6H)-ol 在 吡啶 、 氢氧化钾 、 臭氧 、 三苯基膦 作用下， 以 甲醇 为溶剂， 反应 60.58h， 生成 14-formylmethyl-3-methoxy-14β-estra-1,3,5(10)-trien-17-one
  参考文献：
  名称：

  Cycloaddition-fragmentation route to 14β-allylestrone and the derived 14α,17α-ethano analogue of estriol

  摘要：

  3-Methoxyestra-1,3,5(10),14,16-pentaen-17-yl acetate (1) undergoes efficient baron trifluoride catalysed cycloaddition at 20 degrees C with. acrolein to give the corresponding 17 beta-acetoxy 14 alpha,17 alpha-etheno 16 alpha-carbaldebyde (2). The derived 16 alpha-tosyloxymethyl intermediates are converted via Wharton fragmentation into 14 beta-allyl derivatives of estrone. Oxidative cleavage of 14-allyl-3-methoxy-14 beta-estra-1,3,5(10)-trien-17-one (14) furnishes the 14 beta-formylmethyl derivative (17). Intramolecular reductive cyclisation of 17, followed by stepwise protection-deprotection of functionality provides an efficient synthetic route to 14,17 alpha-ethanoestra-1,3,5(10)-triene-3,16 alpha,17 beta-triol (23), the structure of which is confirmed with the aid of X-ray crystallographic analysis of the derived triacetate.

  DOI：

  10.1016/s0040-4020(01)80653-0
• 作为产物：
  描述：

  17β-acetoxy-3-methoxy-14,17α-ethenooestra-1,3,5(10)-triene-16α-carbaldahyde 在 10% palladium on active carbon lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 1.83h， 生成 (8R,9S,13S,14S,16S,17S)-16-(hydroxymethyl)-3-methoxy-13-methyl-7,8,9,11,12,13,15,16-octahydro-14,17-ethanocyclopenta[a]phenanthren-17(6H)-ol
  参考文献：
  名称：

  Cycloaddition-fragmentation route to 14β-allylestrone and the derived 14α,17α-ethano analogue of estriol

  摘要：

  3-Methoxyestra-1,3,5(10),14,16-pentaen-17-yl acetate (1) undergoes efficient baron trifluoride catalysed cycloaddition at 20 degrees C with. acrolein to give the corresponding 17 beta-acetoxy 14 alpha,17 alpha-etheno 16 alpha-carbaldebyde (2). The derived 16 alpha-tosyloxymethyl intermediates are converted via Wharton fragmentation into 14 beta-allyl derivatives of estrone. Oxidative cleavage of 14-allyl-3-methoxy-14 beta-estra-1,3,5(10)-trien-17-one (14) furnishes the 14 beta-formylmethyl derivative (17). Intramolecular reductive cyclisation of 17, followed by stepwise protection-deprotection of functionality provides an efficient synthetic route to 14,17 alpha-ethanoestra-1,3,5(10)-triene-3,16 alpha,17 beta-triol (23), the structure of which is confirmed with the aid of X-ray crystallographic analysis of the derived triacetate.

  DOI：

  10.1016/s0040-4020(01)80653-0