3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17-one | 158522-15-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17-one
• 英文别名: (1R,2R,11S,14S,16S)-7-methoxy-14-methylpentacyclo[14.2.1.01,14.02,11.05,10]nonadeca-5(10),6,8,17-tetraen-15-one
• CAS: 158522-15-7
• 化学式: C₂₁H₂₄O₂
• 分子量: 308.42
• InChiKey: SDFWIAIMKMYHCR-BUQAOYBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17-one 在 10% palladium on active carbon 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以99%的产率得到3-methoxy-14,17α-ethanoestra-1,3,5(10)-triene-17-one
  参考文献：
  名称：

  Cycloaddition mediated synthesis and rearrangement of 16-functionalised 14α,17α-etheno-19-norsteroids

  摘要：

  Estra-1,3,5(10),14,16-pentaen-17-yl acetates (1) undergo cycloaddition with 2-acetoxyacrylonitrile to give the corresponding 16 alpha,17 beta-diacetoxy 14 alpha,17 alpha-etheno 16 beta-carbonitriles (3), accompanied by minor regio- and stereoisomers depending upon reaction conditions. An X-ray crystal structure analysis of the major isomer derived from the reaction with 1b(3-OAc) confirmed the structure as 3,16 alpha,17 beta-triacetoxy-14,17 beta-ethenoestratriene-16 beta-carbonitrile (3b). Hydrolysis of the 16 alpha-acetoxy 16 beta-cyano moiety of 3 furnishes 17 beta-hydroxy 16-ketones which undergo stereoselective reduction to give mainly the corresponding 16 beta,17 beta-diols. Acid-mediated rearrangement of these diols or base treatment of the derived 17 beta-hydroxy 16 beta-mesylates results in ready 17(1)(17 --> 16)abeo rearrangement, thus providing synthetic access to 14 alpha,16 alpha-ethano derivatives of estrone.

  DOI：

  10.1016/s0040-4020(01)80652-9
• 作为产物：
  描述：

  3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-16β,17β-diol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以86%的产率得到3-methoxy-14,17α-ethenoestra-1,3,5(10)-triene-17-one
  参考文献：
  名称：

  Cycloaddition mediated synthesis and rearrangement of 16-functionalised 14α,17α-etheno-19-norsteroids

  摘要：

  Estra-1,3,5(10),14,16-pentaen-17-yl acetates (1) undergo cycloaddition with 2-acetoxyacrylonitrile to give the corresponding 16 alpha,17 beta-diacetoxy 14 alpha,17 alpha-etheno 16 beta-carbonitriles (3), accompanied by minor regio- and stereoisomers depending upon reaction conditions. An X-ray crystal structure analysis of the major isomer derived from the reaction with 1b(3-OAc) confirmed the structure as 3,16 alpha,17 beta-triacetoxy-14,17 beta-ethenoestratriene-16 beta-carbonitrile (3b). Hydrolysis of the 16 alpha-acetoxy 16 beta-cyano moiety of 3 furnishes 17 beta-hydroxy 16-ketones which undergo stereoselective reduction to give mainly the corresponding 16 beta,17 beta-diols. Acid-mediated rearrangement of these diols or base treatment of the derived 17 beta-hydroxy 16 beta-mesylates results in ready 17(1)(17 --> 16)abeo rearrangement, thus providing synthetic access to 14 alpha,16 alpha-ethano derivatives of estrone.

  DOI：

  10.1016/s0040-4020(01)80652-9

文献信息

• Cycloaddition mediated synthesis and rearrangement of 16-functionalised 14α,17α-etheno-19-norsteroids
  作者：James R Bull、Claudia Grundler、Henry Laurent、Rolf Bohlmann、Anke Müller-Fahrnow

  DOI：10.1016/s0040-4020(01)80652-9

  日期：1994.1

  Estra-1,3,5(10),14,16-pentaen-17-yl acetates (1) undergo cycloaddition with 2-acetoxyacrylonitrile to give the corresponding 16 alpha,17 beta-diacetoxy 14 alpha,17 alpha-etheno 16 beta-carbonitriles (3), accompanied by minor regio- and stereoisomers depending upon reaction conditions. An X-ray crystal structure analysis of the major isomer derived from the reaction with 1b(3-OAc) confirmed the structure as 3,16 alpha,17 beta-triacetoxy-14,17 beta-ethenoestratriene-16 beta-carbonitrile (3b). Hydrolysis of the 16 alpha-acetoxy 16 beta-cyano moiety of 3 furnishes 17 beta-hydroxy 16-ketones which undergo stereoselective reduction to give mainly the corresponding 16 beta,17 beta-diols. Acid-mediated rearrangement of these diols or base treatment of the derived 17 beta-hydroxy 16 beta-mesylates results in ready 17(1)(17 --> 16)abeo rearrangement, thus providing synthetic access to 14 alpha,16 alpha-ethano derivatives of estrone.