(2S,4aS,10aS)-1,2,3,4,4a,9,10,10a-octahydro-7-hydroxy-2-methyl-2-phenanthrenecarboxaldehyde | 104849-43-6

• 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: (2S,4aS,10aS)-1,2,3,4,4a,9,10,10a-octahydro-7-hydroxy-2-methyl-2-phenanthrenecarboxaldehyde
• 英文别名: [2S-(2α,4aα,10aβ)]-1,2,3,4,4a,9,10,10a-Octahydro-7-hydroxy-2-methyl-2-phenanthrenecarboxaldehyde；(2S,4aS,10aS)-7-hydroxy-2-methyl-3,4,4a,9,10,10a-hexahydro-1H-phenanthrene-2-carbaldehyde
• CAS: 104849-43-6
• 化学式: C₁₆H₂₀O₂
• 分子量: 244.334
• InChiKey: IKRPZHKBLKELII-RCBQFDQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S,4aS,10aS)-1,2,3,4,4a,9,10,10a-octahydro-7-hydroxy-2-methyl-2-phenanthrenecarboxaldehyde 在 jones reagent 作用下， 以 四氢呋喃 、 乙醇 、 丙酮 为溶剂， 反应 1.5h， 生成 (17S)-14,15-secoestra-1,3,5(10)-trien-15-yne-3,17-diol
  参考文献：
  名称：

  Preparation of 14,15-secoestra-1,3,5(10)-trien-15-ynes, inhibitors of estradiol dehydrogenase

  摘要：

  The conversion of estrone to 14,15-secoestratrien-15-ynes, inactivators of estradiol dehydrogenase from human term placenta, is described. The optically pure precursor 7-acetoxy-octahydro-2-phenanthrenecarboxylic acid methyl ester is prepared from estrone in five steps and 40% yield. The unsubstituted propargylic secoestratriene diol, a mechanism-based inactivator of estradiol dehydrogenase, and the corresponding acetylenic ketone, an affinity label inactivator of the same enzyme, arise from the phenanthrene ester in three and four steps. The propargylic secoestratriene diol also competes with [3H]estradiol for binding to calf uterus estrogen receptor and possesses weak uterotrophic activity.

  DOI：

  10.1016/0039-128x(89)90147-5
• 作为产物：
  描述：

  (2S,4aS,10aS)-1,2,3,4,4a,9,10,10a-octahydro-7-hydroxy-2-methyl-2-phenanthrenemethanol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到(2S,4aS,10aS)-1,2,3,4,4a,9,10,10a-octahydro-7-hydroxy-2-methyl-2-phenanthrenecarboxaldehyde
  参考文献：
  名称：

  Preparation of 14,15-secoestra-1,3,5(10)-trien-15-ynes, inhibitors of estradiol dehydrogenase

  摘要：

  The conversion of estrone to 14,15-secoestratrien-15-ynes, inactivators of estradiol dehydrogenase from human term placenta, is described. The optically pure precursor 7-acetoxy-octahydro-2-phenanthrenecarboxylic acid methyl ester is prepared from estrone in five steps and 40% yield. The unsubstituted propargylic secoestratriene diol, a mechanism-based inactivator of estradiol dehydrogenase, and the corresponding acetylenic ketone, an affinity label inactivator of the same enzyme, arise from the phenanthrene ester in three and four steps. The propargylic secoestratriene diol also competes with [3H]estradiol for binding to calf uterus estrogen receptor and possesses weak uterotrophic activity.

  DOI：

  10.1016/0039-128x(89)90147-5

文献信息

• Method and compositions for increasing bone mass
  申请人：Manolagas C. Stavros

  公开号：US20050026223A1

  公开（公告）日：2005-02-03

  The invention as disclosed provides a method to increase bone mass without compromising bone strength or quality, through the administration to a host of a compound that binds to the estrogen or androgen receptor without causing hormonal transcriptional activation.

  本发明提供了一种方法，通过向宿主施用与雌激素或雄激素受体结合而不引起激素转录激活的化合物，在不影响骨强度或骨质量的情况下增加骨量。
• Trifluoromethylacetylenic alcohols as affinity labels: inactivation of estradiol dehydrogenase by a trifluoromethylacetylenic secoestradiol
  作者：Saurabh S. Lawate、Douglas F. Covey

  DOI：10.1021/jm00171a002

  日期：1990.9
• AUCHUS, RICHARD J.;PALMER, JAMES O.;CARRELL, H. L.;COVEY, DOUGLAS F., STEROIDS, 51,(1989) N-2, C. 77-96
  作者：AUCHUS, RICHARD J.、PALMER, JAMES O.、CARRELL, H. L.、COVEY, DOUGLAS F.

  DOI：——

  日期：——
• COVEY, DOUGLAS F.;AUCHUS, RICHARD J.
  作者：COVEY, DOUGLAS F.、AUCHUS, RICHARD J.

  DOI：——

  日期：——
• Methods of screening for apoptosis-controlling agents for bone anabolic therapies and uses thereof
  申请人：——

  公开号：US20040224884A1

  公开（公告）日：2004-11-11

  The invention as disclosed provides a method to increase bone mass without compromising bone strength or quality, through the administration to a host of a compound that binds to the estrogen or androgen receptor without causing hormonal transcriptional activation.