16β-methanesulfonyloxy-3-methoxy-14,17α-ethanoestra-1,3,5(10)-triene-17β-yl acetate | 158522-14-6

• 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: 16β-methanesulfonyloxy-3-methoxy-14,17α-ethanoestra-1,3,5(10)-triene-17β-yl acetate
• CAS: 158522-14-6
• 化学式: C₂₄H₃₂O₆S
• 分子量: 448.58
• InChiKey: DOMASVIUGUFFEO-PPOWDTIZSA-N

物化性质

• 沸点：
  591.0±50.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  78.9
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  16β-methanesulfonyloxy-3-methoxy-14,17α-ethanoestra-1,3,5(10)-triene-17β-yl acetate 在 aluminum oxide 、 氢氧化钾 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以80%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：

  [(1S,2R,11S,14S,15R)-7-methoxy-14-methyl-16-oxo-15-pentacyclo[13.2.2.01,14.02,11.05,10]nonadeca-5(10),6,8-trienyl] acetate 在 吡啶 、 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 78.75h， 生成 16β-methanesulfonyloxy-3-methoxy-14,17α-ethanoestra-1,3,5(10)-triene-17β-yl acetate
  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