16α-<3-(trimethylsilyl)-2-propynyl>-3-<(tert-butyldimethylsilyl)oxy>estra-1,3,5(10)-trien-17β-ol | 106139-65-5

• 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: 16α-<3-(trimethylsilyl)-2-propynyl>-3-<(tert-butyldimethylsilyl)oxy>estra-1,3,5(10)-trien-17β-ol
• CAS: 106139-65-5
• 化学式: C₃₀H₄₈O₂Si₂
• 分子量: 496.881
• InChiKey: DIFHJVRUVNOMBH-BWFCKMRWSA-N

物化性质

• 沸点：
  525.0±50.0 °C(Predicted)
• 密度：
  0.995±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.78
• 重原子数：
  34.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  16α-<3-(trimethylsilyl)-2-propynyl>-3-<(tert-butyldimethylsilyl)oxy>estra-1,3,5(10)-trien-17β-ol 在 甲醇 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以89.4%的产率得到16α-(2-propynyl)estra-1,3,5(10)-triene-3,17β-diol
  参考文献：
  名称：

  Estrogen receptor binding tolerance of 16α-substituted estradiol derivatives

  摘要：

  In order to examine the tolerance of the estrogen receptor for 16 alpha-substituents in estradiol, we have synthesized various 16 alpha-substituted estrogens and determined their binding affinity for receptor by a competitive radiometric binding assay. The substituents ranged from small, single-atom substituents (halogens), two-atom substituents (halomethyl groups), to larger alkyl groups and ultimately alkyl groups bearing various functionality, including fluorescent (nitrobenzoxadiazole, NBD) and photoreactive (nitroazidophenyl, NAP) groups. The estrogen receptor seems to have a moderate tolerance for bulky substituents: All of the halogen and halomethyl substituents bind with an affinity at least 50% that of estradiol; in the three atom alkyl series, the affinity declined markedly from propargyl (44%) and allyl (38%) to propyl (5%), suggestive of detailed steric constraints or a preference for unsaturation. The larger, more highly functionalized derivatives ranged in affinity from 0.1-7%, with the highest affinity binders being benzyl (5%) and 4-phenoxy-2(E)-butenyl (7%); most of the lowest affinity ones were the bulky fluorescent and photoreactive derivatives. Thus, the estrogen receptor has good tolerance for estradiol derivatives substituted at the 16 alpha-position with nonpolar groups of moderate bulk; however, with groups of larger bulk, affinity is much lower and becomes highly dependent upon the polarity and detailed structure of the substituents.

  DOI：

  10.1016/0039-128x(88)90046-3
• 作为产物：
  描述：

  3-(O-tert-butyl(dimethyl)silyl)estrone 在 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 生成 16α-<3-(trimethylsilyl)-2-propynyl>-3-<(tert-butyldimethylsilyl)oxy>estra-1,3,5(10)-trien-17β-ol
  参考文献：
  名称：

  A short, stereoselective route to 16.alpha.-(substituted-alkyl)estradiol derivatives

  摘要：

  DOI：

  10.1021/jo00378a015

文献信息

• A short, stereoselective route to 16.alpha.-(substituted-alkyl)estradiol derivatives
  作者：Thomas L. Fevig、John A. Katzenellenbogen

  DOI：10.1021/jo00378a015

  日期：1987.1
• Estrogen receptor binding tolerance of 16α-substituted estradiol derivatives
  作者：Thomas L. Fevig、Michael K. Mao、John A. Katzenellenbogen

  DOI：10.1016/0039-128x(88)90046-3

  日期：1988.5

  In order to examine the tolerance of the estrogen receptor for 16 alpha-substituents in estradiol, we have synthesized various 16 alpha-substituted estrogens and determined their binding affinity for receptor by a competitive radiometric binding assay. The substituents ranged from small, single-atom substituents (halogens), two-atom substituents (halomethyl groups), to larger alkyl groups and ultimately alkyl groups bearing various functionality, including fluorescent (nitrobenzoxadiazole, NBD) and photoreactive (nitroazidophenyl, NAP) groups. The estrogen receptor seems to have a moderate tolerance for bulky substituents: All of the halogen and halomethyl substituents bind with an affinity at least 50% that of estradiol; in the three atom alkyl series, the affinity declined markedly from propargyl (44%) and allyl (38%) to propyl (5%), suggestive of detailed steric constraints or a preference for unsaturation. The larger, more highly functionalized derivatives ranged in affinity from 0.1-7%, with the highest affinity binders being benzyl (5%) and 4-phenoxy-2(E)-butenyl (7%); most of the lowest affinity ones were the bulky fluorescent and photoreactive derivatives. Thus, the estrogen receptor has good tolerance for estradiol derivatives substituted at the 16 alpha-position with nonpolar groups of moderate bulk; however, with groups of larger bulk, affinity is much lower and becomes highly dependent upon the polarity and detailed structure of the substituents.