3,9-dimethoxy-6aα,6bβ,12aβ,12bα-tetrahydrodibenzo(a,g)biphenylene-5,11(6H,12H)dione | 75456-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 3,9-dimethoxy-6aα,6bβ,12aβ,12bα-tetrahydrodibenzo(a,g)biphenylene-5,11(6H,12H)dione
• 英文别名: 3,9-dimethoxy-6aα,6bβ,12aβ,12bα-tetrahydrodibenzobiphenylene-5,11(6H,12H)dione；3,9-dimethoxy-6aα,6bβ,12aβ,12bα-tetrahydrodibenzo[a,g]biphenylene-5,11(6H,12H)dione
• CAS: 75456-20-1
• 化学式: C₂₂H₂₀O₄
• 分子量: 348.398
• InChiKey: VBJCEWQZLCBLDD-LHKLFAJASA-N

物化性质

• 熔点：
  170-171 °C
• 沸点：
  548.2±50.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.99
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3,9-dimethoxy-6aα,6bβ,12aβ,12bα-tetrahydrodibenzo(a,g)biphenylene-5,11(6H,12H)dione 在 palladium on activated charcoal 氢气 、 三溴化硼 、 镍 作用下， 以 二氯甲烷 为溶剂， 反应 16.25h， 生成 3,9-Dihydroxyoctahydrodibenzo(a,g)biphenylene
  参考文献：
  名称：

  Synthesis and antifertility activity of 3,9-dihydroxy-5,6,6a.alpha.,6b.beta.,11,12,12a.beta.,12b.alpha.-octahydrodibenzo[a,g]biphenylene, a structural relative of diethylstilbestrol

  摘要：

  The title diphenol, 1a, was synthesized from p,p'-dihydroxy-alpha-truxillic acid and shown to be active as an oral postcoital antifertility agent in rats: ED100 = 100 (micrograms/kg)/day. The oral uterotropic potency was estimated to be 16% of that of diethylstilbestrol (95% confidence limits of potency 8--35%). The structure of the diphenol, 1a, was confirmed by single-crystal X-ray analysis of the dimethyl ether.

  DOI：

  10.1021/jm00186a023
• 作为产物：
  描述：

  (1a,2a,3b,4b)-2,4-二(4-羟基苯基)-1,3-环丁烷二甲酸 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 PPA 、 silver benzoate 、 三乙胺 作用下， 以 乙醚 、 苯 为溶剂， 反应 32.08h， 生成 3,9-dimethoxy-6aα,6bβ,12aβ,12bα-tetrahydrodibenzo(a,g)biphenylene-5,11(6H,12H)dione
  参考文献：
  名称：

  Synthesis and antifertility activity of 3,9-dihydroxy-5,6,6a.alpha.,6b.beta.,11,12,12a.beta.,12b.alpha.-octahydrodibenzo[a,g]biphenylene, a structural relative of diethylstilbestrol

  摘要：

  The title diphenol, 1a, was synthesized from p,p'-dihydroxy-alpha-truxillic acid and shown to be active as an oral postcoital antifertility agent in rats: ED100 = 100 (micrograms/kg)/day. The oral uterotropic potency was estimated to be 16% of that of diethylstilbestrol (95% confidence limits of potency 8--35%). The structure of the diphenol, 1a, was confirmed by single-crystal X-ray analysis of the dimethyl ether.

  DOI：

  10.1021/jm00186a023