3-hydroxy-14,15-secoestra-1,3,5(10)-trien-15-yn-17-one | 104849-42-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 3-hydroxy-14,15-secoestra-1,3,5(10)-trien-15-yn-17-one
• 英文别名: 1-[(2S,4aS,10aS)-7-hydroxy-2-methyl-3,4,4a,9,10,10a-hexahydro-1H-phenanthren-2-yl]prop-2-yn-1-one
• CAS: 104849-42-5
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: HYTVYLVVJDEURY-OWQGQXMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-hydroxy-14,15-secoestra-1,3,5(10)-trien-15-yn-17-one 以 乙醇 为溶剂， 反应 1.5h， 以60%的产率得到(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-phenanthrenecarboxaldehyde 在 jones reagent 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 生成 3-hydroxy-14,15-secoestra-1,3,5(10)-trien-15-yn-17-one
  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

• 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：——
• US4874891A
  申请人：——

  公开号：US4874891A

  公开（公告）日：1989-10-17