3,9α,17β-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether | 1923-05-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子
• 英文名称: 3,9α,17β-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether
• 英文别名: 17β-Acetoxy-9α-hydroxy-3-methoxy-oestratrien-(1.3.5,10)-on-(11)；9α,17β-dihydroxy-3-methoxy-11-oxo-estra-1,3,5(10)-triene 17-acetate
• CAS: 1923-05-3
• 化学式: C₂₁H₂₆O₅
• 分子量: 358.434
• InChiKey: LMPPBSCTXXHHGL-XYYCENQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,9α,17β-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether 在 sodium hydroxide 、 迭氮酸 、 乙醇 、 三氟化硼乙醚 作用下， 以 苯 为溶剂， 反应 40.08h， 生成 11-aza-3,17β-dihydroxy-C-homoestra-1,3,5(10),8(9)-tetraen-12-one 3-methyl ether
  参考文献：
  名称：

  Synthesis of novel 6-aza-B- and 11-aza-C-homoestranes as antifertility agents

  摘要：

  Reaction of 3,9alpha,17beta-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether (3) with N3H-BF3 etherate leads mainly to lactam (4) along with the N-azido compound (5) as a minor product. Under similar conditions, 3,17beta-dihydroxyestra-1,3,5(10)-trien-6-one 17-acetate 3-methyl ether gives lactam (12) and the tetrazolo derivative (9). Similar reaction of the diacetate (8) gives only the tetrazole derivative (11). Compounds 4, 6, and 10 prevent implantation in rats at 5-, 10-, and 5-mg/kg doses, respectively. Compounds 4, 6, 9, and 10 show significant estrogenic activity at the respective contraceptive doses.

  DOI：

  10.1016/0039-128x(93)90055-r
• 作为产物：
  描述：

  雌二醇 3-甲基醚 17-乙酸酯 在 chromium(VI) oxide 、 溶剂黄146 作用下， 以 水 为溶剂， 以50%的产率得到3,9α,17β-trihydroxyestra-1,3,5(10)-trien-11-one 17-acetate 3-methyl ether
  参考文献：
  名称：

  Synthesis and in vivo evaluation of 11-substituted estradiol derivatives as anti-implantation agents

  摘要：

  Synthesis of 11-substituted estradiol derivatives (12-17) has been carried out by the Grignard reaction with alkyl, allyl, and benzyl halides on 17 beta-hydroxy-3-methoxy-11-oxo-estra-1,3,5(10), 8(9)-tetraene (10). The novel compounds (10 and 12-17) were evaluated for their preliminary post-coital contraceptive (anti-implantation) activity in Sprague-Dawley rats. The tested compounds were administered orally and showed significant anti-implantation activity. Compound 13 is the most potent compound in the series which showed 100% contraceptive efficacy at 1.25 mg kg (1). (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.093