14-formylmethyl-3-methoxy-14β-estra-1,3,5(10),15-tetraene-17-one | 158522-12-4

• 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: 14-formylmethyl-3-methoxy-14β-estra-1,3,5(10),15-tetraene-17-one
• CAS: 158522-12-4
• 化学式: C₂₁H₂₄O₃
• 分子量: 324.42
• InChiKey: JEGAVPIVYCTSPW-UKAVVXHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 14-formylmethyl-3-methoxy-14β-estra-1,3,5(10),15-tetraene-17-one 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以93%的产率得到3,5'ξ-dimethoxy-15αH-dihydrofuro<3',2';14,15>-14β-estra-1,3,5(10)-trien-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 sodium periodate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以95 mg的产率得到14-formylmethyl-3-methoxy-14β-estra-1,3,5(10),15-tetraene-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