(5S,6R)-5-(4-Hydroxy-phenyl)-6-phenyl-5,6,7,8-tetrahydro-naphthalen-2-ol | 72105-62-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5S,6R)-5-(4-Hydroxy-phenyl)-6-phenyl-5,6,7,8-tetrahydro-naphthalen-2-ol
• CAS: 72105-62-5
• 化学式: C₂₂H₂₀O₂
• 分子量: 316.4
• InChiKey: AQRJVZJHYJLAEV-RBBKRZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-碘-2,3-丙二醇 、 (5S,6R)-5-(4-Hydroxy-phenyl)-6-phenyl-5,6,7,8-tetrahydro-naphthalen-2-ol 生成 3-{(5S,6R)-5-[4-(2,3-Dihydroxy-propoxy)-phenyl]-6-phenyl-5,6,7,8-tetrahydro-naphthalen-2-yloxy}-propane-1,2-diol
  参考文献：
  名称：

  Antiestrogens and antiestrogen metabolites: preparation of tritium-labeled (.+-.)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol and characterization and synthesis of a biologically important metabolite

  摘要：

  The Upjohn antiestrogen (+/-)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol (2b, U 23469) has been prepared in tritium-labeled form by reduction of an unsaturated dihydronaphthalene precursor with carrier-free tritium gas over a palladium catalyst followed by alkylation with 3-iodo-1,2-propanediol. After extensive chromatographic purification, the final material was obtained with a specific activity of 13 Ci/mmol and a radiochemical purity of 94%. In vivo studies with immature rats show that [3H]2b is slowly converted to a more polar metabolite that is selectively accumulated in the nuclear fraction of the uterus where it is bound to the estrogen receptor. Chromatographic comparisons indicate that this metabolite is the demethylated analogue 2c, a compound that has an affinity for estrogen receptor more than 300 times greater than that of 2b. These studies suggest that the demethylated analogue 2c may be a biologically important metabolite of 2b that is involved in the action of this antiestrogen.

  DOI：

  10.1021/jm00198a015
• 作为产物：
  描述：

  4-(6-甲氧基-2-苯基-3,4-二氢萘并醛烯-1-基)苯酚 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 生成 (5S,6R)-5-(4-Hydroxy-phenyl)-6-phenyl-5,6,7,8-tetrahydro-naphthalen-2-ol
  参考文献：
  名称：

  Antiestrogens and antiestrogen metabolites: preparation of tritium-labeled (.+-.)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol and characterization and synthesis of a biologically important metabolite

  摘要：

  The Upjohn antiestrogen (+/-)-cis-3-[p-(1,2,3,4-tetrahydro-6-methoxy-2-phenyl-1-naphthyl)phenoxy]-1,2-propanediol (2b, U 23469) has been prepared in tritium-labeled form by reduction of an unsaturated dihydronaphthalene precursor with carrier-free tritium gas over a palladium catalyst followed by alkylation with 3-iodo-1,2-propanediol. After extensive chromatographic purification, the final material was obtained with a specific activity of 13 Ci/mmol and a radiochemical purity of 94%. In vivo studies with immature rats show that [3H]2b is slowly converted to a more polar metabolite that is selectively accumulated in the nuclear fraction of the uterus where it is bound to the estrogen receptor. Chromatographic comparisons indicate that this metabolite is the demethylated analogue 2c, a compound that has an affinity for estrogen receptor more than 300 times greater than that of 2b. These studies suggest that the demethylated analogue 2c may be a biologically important metabolite of 2b that is involved in the action of this antiestrogen.

  DOI：

  10.1021/jm00198a015