(17α,20E)-21-(phenylseleno)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol | 108561-04-2

• 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: (17α,20E)-21-(phenylseleno)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol
• 英文别名: (8R,9S,13S,14S,17R)-13-methyl-17-[(E)-2-phenylselanylethenyl]-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
• CAS: 108561-04-2
• 化学式: C₂₆H₃₀O₂Se
• 分子量: 453.483
• InChiKey: RJZRUPAYMZVQHJ-DWBUVMIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.52
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苯基二硒醚 、 (17α,20E)-21-(tributylstannyl)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 在 溴 作用下， 生成 (17α,20E)-21-(phenylseleno)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol
  参考文献：
  名称：

  Electrophilic destannylation: stereospecific introduction of electrophiles at the 21 position of (17.alpha.)-19-norpregna-1,3,5(10),20-tetraene-3,17.beta.-diols

  摘要：

  DOI：

  10.1021/jo00392a036

文献信息

• Synthesis and estrogen receptor binding of (17α,20E)- and (17α,20Z)-21-phenylthio- and 21-phenylseleno-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols
  作者：Elio Napolitano、Rita Fiaschi、Lee W. Herman、Robert N. Hanson

  DOI：10.1016/0039-128x(96)00045-1

  日期：1996.6

  Previous studies from our laboratory using 17 alpha-E- and 17 alpha-Z-halovinyl estradiols demonstrated a marked enhancement of receptor binding by the Z-isomers. This suggested tolerance at the 17 alpha-position was not previously observed by investigations using 16 alpha and 17 alpha-substituted estradiols. Because of the synthetic access provided by vinyl tin chemistry, lye prepared the 17 alpha-E and Z-phenylthiovinyl and phenylselenovinyl estradiols and compared their binding characteristics to those of the previously reported 16 alpha/17 alpha-phenylseleno and methylseleno estradiols. The results, in addition to demonstrating a facile preparation of the target compounds, indicated that significant receptor affinity was retained by these compounds (relative binding affinity = 24.5-117). The highest affinity was demonstrated by the 17 alpha-Z-phenylthiovinyl estradiol 5a, which, by molecular modeling, exhibited a significantly different molecular conformation from the corresponding 17 alpha-E-phenylthiovinyl isomer or the 17 alpha-phenyl-thioethynyl analog. The current series possessed better binding characteristics than the phenylseleno and methylseleno estradiols brit somewhat poorer binding than the 17 alpha-phenylthiovinyl series. The observations suggest that some steric limitations exist ill a portion of the 17 alpha-region, and that the region is better accessed by compounds possessing Z-vinyl stereochemistry.