(8'S,9'S,11'S,13'S,14'S)-11'-methoxy-13'-methyl-3'-phenylmethoxyspiro[1,3-dioxolane-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene] | 83274-63-9

• 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: (8'S,9'S,11'S,13'S,14'S)-11'-methoxy-13'-methyl-3'-phenylmethoxyspiro[1,3-dioxolane-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene]
• CAS: 83274-63-9
• 化学式: C₂₈H₃₄O₄
• 分子量: 434.576
• InChiKey: GWNIHZINGBPZQR-JUCVYKANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (8'S,9'S,11'S,13'S,14'S)-11'-methoxy-13'-methyl-3'-phenylmethoxyspiro[1,3-dioxolane-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene] 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 11β-methoxyestrone
  参考文献：
  名称：

  Novel Estradiol Derivatives Labeled with Ru, W, and Co Complexes. Influence on Hormone-Receptor Affinity of Several Organometallic Groups at the 17 Position

  摘要：

  In order to elucidate the extent to which recognition of the estrogen receptor is influenced by addition of an organometallic substituent at the 17alpha position, modification of 17beta-estradiol at this position was carried out by using the organometallic groups -CdropC-(eta(5)-C5H4)RuCp, CH2-(eta(5)-C5H4)RuCp, -CdropC-(eta(5)-C5H4)-W(CO)(3)(Me), -(CdropCCHO)Co-2(CO)(6), and -(CdropCCH(2)OH)CO2(CO)(6). The relative binding affinity (RBA) values for estradiol receptor alpha showed that recognition was good (RBA between 20 and 13.5%) when the organometallic moiety was attached at the end of a rigid alkyne spacer. However, the affinity of the modified hormone for the receptor was severely reduced. (RBA = 1%) for a substituent such as -CH2-(eta(5)-C5H4)-RuCp, in which the spacer is reduced to a single flexible sp(3) carbon atom, allowing the organometallic moiety greater freedom of movement around the attachment point. The RBA values found were in agreement with results obtained from a molecular-modeling study in which 5, an organometallic hormone with a rigid spacer, or 7, a molecule with a flexible spacer, was inserted into the cavity of the recently characterized Ligand-Binding Domain of estrogen receptor alpha.

  DOI：

  10.1002/1521-3765(20021115)8:22<5241::aid-chem5241>3.0.co;2-m
• 作为产物：
  描述：

  3-benxyloxy-17,17-ethylenedioxyestra-1,3,5(10)-trien-11β-ol 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 14.0h， 以71%的产率得到(8'S,9'S,11'S,13'S,14'S)-11'-methoxy-13'-methyl-3'-phenylmethoxyspiro[1,3-dioxolane-2,17'-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene]
  参考文献：
  名称：

  Novel Estradiol Derivatives Labeled with Ru, W, and Co Complexes. Influence on Hormone-Receptor Affinity of Several Organometallic Groups at the 17 Position

  摘要：

  In order to elucidate the extent to which recognition of the estrogen receptor is influenced by addition of an organometallic substituent at the 17alpha position, modification of 17beta-estradiol at this position was carried out by using the organometallic groups -CdropC-(eta(5)-C5H4)RuCp, CH2-(eta(5)-C5H4)RuCp, -CdropC-(eta(5)-C5H4)-W(CO)(3)(Me), -(CdropCCHO)Co-2(CO)(6), and -(CdropCCH(2)OH)CO2(CO)(6). The relative binding affinity (RBA) values for estradiol receptor alpha showed that recognition was good (RBA between 20 and 13.5%) when the organometallic moiety was attached at the end of a rigid alkyne spacer. However, the affinity of the modified hormone for the receptor was severely reduced. (RBA = 1%) for a substituent such as -CH2-(eta(5)-C5H4)-RuCp, in which the spacer is reduced to a single flexible sp(3) carbon atom, allowing the organometallic moiety greater freedom of movement around the attachment point. The RBA values found were in agreement with results obtained from a molecular-modeling study in which 5, an organometallic hormone with a rigid spacer, or 7, a molecule with a flexible spacer, was inserted into the cavity of the recently characterized Ligand-Binding Domain of estrogen receptor alpha.

  DOI：

  10.1002/1521-3765(20021115)8:22<5241::aid-chem5241>3.0.co;2-m