3-acetoxy-16α,17α-epoxy-19-norpregna-1,3,5(10)-trien-20-yne | 55812-84-5

• 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: 3-acetoxy-16α,17α-epoxy-19-norpregna-1,3,5(10)-trien-20-yne
• 英文别名: [(1R,2S,4R,6S,7S,10S)-6-ethynyl-7-methyl-5-oxapentacyclo[8.8.0.02,7.04,6.011,16]octadeca-11(16),12,14-trien-14-yl] acetate
• CAS: 55812-84-5
• 化学式: C₂₂H₂₄O₃
• 分子量: 336.431
• InChiKey: CTMMNYCYSQVDGS-OVQJPPBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetoxy-16α,17α-epoxy-19-norpregna-1,3,5(10)-trien-20-yne 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 3-hydroxy-19-norpregna-1,3,5(10),16-tetraen-20-yne
  参考文献：
  名称：

  Synthesis and estrogenic properties of 17-epi-ethynylestradiol and its ether derivatives epimestranol and epiquinestrol

  摘要：

  The synthesis of 17-epi-ethynylestradiol (10), the 17 beta-ethynyl-17 alpha-ol epimer of the well-known orally active estrogen, ethynylestradiol (1), was achieved by LiA1H4 reduction of epoxide 9, as well as by demethylating epimestranol (11) with CH3MgI. Compound 11 was obtained by the unusual 17 beta-ethynylation of estrone 3-methyl ether 22 under equilibrating conditions. The in vitro estrogen receptor-binding affinity and the oral estrogenicity in the rat for the 17-epi compounds 10, 11 and 20 (epiquinestrol) was evaluated. Despite moderate estrogen receptor-binding affinity, compound 10 was devoid of measurable estrogenicity at 10 mg/kg or antiestrogenicity at 3 mg/kg.

  DOI：

  10.1021/jm00198a021

文献信息

• US3983112A
  申请人：——

  公开号：US3983112A

  公开（公告）日：1976-09-28
• US4022892A
  申请人：——

  公开号：US4022892A

  公开（公告）日：1977-05-10