17aβ-acetoxy-3-methoxy-D-homo-8α-estra-1,3,5(10)-triene | 2930-76-9

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 17aβ-acetoxy-3-methoxy-D-homo-8α-estra-1,3,5(10)-triene
• 英文别名: [(1S,4aS,4bS,10bS,12aS)-8-methoxy-12a-methyl-2,3,4,4a,4b,5,6,10b,11,12-decahydro-1H-chrysen-1-yl] acetate
• CAS: 2930-76-9
• 化学式: C₂₂H₃₀O₃
• 分子量: 342.478
• InChiKey: YRAJYNGPNLOZQO-FXTUREPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  17aβ-acetoxy-3-methoxy-D-homo-8α-estra-1,3,5(10)-triene 在 sodium tetrahydroborate 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 二乙二醇二甲醚 为溶剂， 以64%的产率得到3-methoxy-17αb-ethoxy-D-homo-8-isoestra-1,3,5(10)-triene
  参考文献：
  名称：

  摘要：

  New modulators of estradiol receptors were synthesized, 17(gamma-alkoxy-3-oxo-8-isoestr-5(10)-enes) and the respective D-homoanalogs. Reaction of these compounds with CuBr2 in acetonitrile famished steroids with aromatic A ring possessing hypocholesterolemic and osteoprotective activity.

  DOI：

  10.1023/a:1025584018313
• 作为产物：
  描述：

  17aβ-acetoxy-3-methoxy-D-homoestra-1,3,5(10),8,14-pentaene 在 氢气 作用下， 以 苯 为溶剂， 60.0~70.0 ℃ 、15.69 MPa 条件下， 以95%的产率得到17aβ-acetoxy-3-methoxy-D-homo-8α-estra-1,3,5(10)-triene
  参考文献：
  名称：

  Catalytic hydrogenation on Raney nickel of estra-1,3,5(10),8,14-pentaenes with sterically accessible double bonds

  摘要：

  The catalytic hydrogenation of estra-1,3,5(10),8,14-pentaenes with sterically accessible double bonds in the presence of Raney nickel in 2-propanol at elevated pressure and at heating to 110-120 degrees C resulted in prevailing formation of estrogens 8 alpha-analogs alongside a considerable quantity of estra-5,7,9-trienes. Although the hydrogenation at 45-60 degrees C provided a higher yield of estrogens 8 alpha-analogs, the synthesis of steroids of this group gave better results at hydrogenation in a high purity benzene.

  DOI：

  10.1134/s1070428008050060

文献信息

• Synthesis and biological activity of some 8α-analogs of steroidal estrogens
  作者：S. N. Morozkina、Sh. N. Abusalimov、S. I. Selivanov、A. G. Shavva

  DOI：10.1134/s1070428013040180

  日期：2013.4

  8 alpha-Analogs of steroidal estrogens containing a methyl group on C-1 or an oxo group on C-6 were synthesized with a view to obtain compounds exhibiting selective biological activity, and their steric structure was studied. As shown with 1,3-O-dimethyl-8 alpha-estrone as an example, such compounds in solution can exist as two conformers, whereas the oxo group on C-6 almost does not affect conformation of the modified derivative as compared to the parent structure. Some newly synthesized compounds exhibited hypocholesterolemic activity in combination with reduced uterotropic effect, which is important for the design of drugs for the treatment of atherosclerosis. 6-Oxo-8 alpha-analogs showed osteoprotective activity, so that introduction of an oxo group into the 6-position is promising from the viewpoint of hormone replacement therapy.
• Shavva, A. G.; Eliseev, I. I.; Burova, E. B., Russian Journal of Organic Chemistry, 1986, vol. 22, p. 391 - 392
  作者：Shavva, A. G.、Eliseev, I. I.、Burova, E. B.、Koval'chuk, S. V.、Gindin, V. A.

  DOI：——

  日期：——