17-acetoxy-3-methoxy-13α-estra-1,3,5(10), 16 tetraene | 25089-53-6

• 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: 17-acetoxy-3-methoxy-13α-estra-1,3,5(10), 16 tetraene
• 英文别名: 3-Methoxy-13α-oestra-1,3,5(10),16-tetraen-17-ol-acetat
• CAS: 25089-53-6
• 化学式: C₂₁H₂₆O₃
• 分子量: 326.436
• InChiKey: RIKGARKVVXQXPM-WERVVEIQSA-N

物化性质

• 沸点：
  465.5±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.61
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  17-acetoxy-3-methoxy-13α-estra-1,3,5(10), 16 tetraene 在 lithium aluminium tetrahydride 、 溴 、 potassium carbonate 作用下， 以 四氯化碳 、 乙醚 为溶剂， 生成 16β-bromo-3-methoxy-13α-estra-1,3,5(10)-triene-17β-ol
  参考文献：
  名称：

  Nambara,T. et al., Chemical and pharmaceutical bulletin, 1969, vol. 17, # 11, p. 2366 - 2370

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酸异丙烯酯 、 3-methoxy-13α-estra-1,3,5(10)-trien-17-one 在 硫酸 、 对甲苯磺酸 作用下， 反应 22.0h， 以71.6%的产率得到17-acetoxy-3-methoxy-13α-estra-1,3,5(10), 16 tetraene
  参考文献：
  名称：

  Synthesis and conformation of four 16,17-diols in the 3-methoxy-13α-estra-1,3,5(10)-triene series

  摘要：

  All four diasteromeric 16,17-diols in the 3-methoxy-13alpha-estra-1,3,5(10)-triene series have been synthesized. The trans-diols 1 and 2 can be obtained by hydroborating the 17-enol acetate 6 (61%, ratio 27:73, preferred alpha attack). OsO4 dihydroxylation of the olefin 7 ;yielded the cis-diols 3 and 4 (ratio 13:87). The dihydroxylation proceeds with preference for beta attack caused b a C-ring twist-boat form of 7. The conformations of the diols 2 and 4, the 17-benzyl-17-hydroxy compounds 9 and 10 (obtained by Grignard reaction), and the 16alpha-bromo-17beta-hydroxy compound 8 were determined by X-ray analysis and by H-1 NMR spectroscopy in solution. Some compounds, in spite of a 17beta-hydroxy group, had a conformation with a ring C chair form (4, 8, 9) caused by intermolecular interaction in the solid state. The rest of the compounds studied here (2, 10) possessed a conformation with a ring C twist-boat form, which has been also found for all 1beta-substituted compounds in solution. The preferred conformation of the D-ring with 17beta-substituents seems to be the 16beta-envelope form or near this form, but the existence of the 16beta-envelope form (inversion of the ring D) for some compounds showed great variance in the conformation of ring D, which is substituent dependent. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00175-7