2-(3-hydroxyphenyl)-1,1-dimethyl-3-propan-2-ylinden-5-ol | 98876-54-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: 2-(3-hydroxyphenyl)-1,1-dimethyl-3-propan-2-ylinden-5-ol
• CAS: 98876-54-1
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: KNXJFEAHASYHKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  乙酸酐 、 2-(3-hydroxyphenyl)-1,1-dimethyl-3-propan-2-ylinden-5-ol 在 吡啶 作用下， 生成 [2-(3-acetyloxyphenyl)-1,1-dimethyl-3-propan-2-ylinden-5-yl] acetate
  参考文献：
  名称：

  2-Phenylindenes. Development of a new mammary tumor-inhibiting antiestrogen by combination of estrogenic side effect-lowering structural elements

  摘要：

  A new antiestrogenic, mammary tumor inhibiting 2-phenylindene was developed by the use of structural elements that we have shown to decrease estrogenic side effects but to increase antiestrogenic activity and retain the antitumor effect of certain stilbenes. The new 2-phenylindenes were synthesized from their corresponding methoxy-substituted 3,4-diphenylhexane-3,4-diols by cyclization with acetyl chloride and acetic anhydride and subsequent ether cleavage and acetylation. In this series, the 2-phenylindene derivative (compound 13) with a 5,6,3',4'-tetraacetoxy and a 1-methyl-3-ethyl substitution had the highest affinity for the estrogen receptor, the strongest antiestrogenic effect, and the lowest estrogenic effect. This compound was superior to the 2-phenylindenes with 5,3'-diacetoxy substitution or 1,1-dimethyl and 3-isopropyl moieties, respectively. Compound 13 exhibited a strong, significant inhibiting effect on the growth of the hormone-dependent MXT mouse mammary tumor without estrogenic side effects.

  DOI：

  10.1021/jm00151a012
• 作为产物：
  描述：

  1-(3-methoxyphenyl)-2-methylpropan-1-one 在 乙酸酐 、 三溴化硼 、 四氯化钛 、 乙酰氯 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 2-(3-hydroxyphenyl)-1,1-dimethyl-3-propan-2-ylinden-5-ol
  参考文献：
  名称：

  2-Phenylindenes. Development of a new mammary tumor-inhibiting antiestrogen by combination of estrogenic side effect-lowering structural elements

  摘要：

  A new antiestrogenic, mammary tumor inhibiting 2-phenylindene was developed by the use of structural elements that we have shown to decrease estrogenic side effects but to increase antiestrogenic activity and retain the antitumor effect of certain stilbenes. The new 2-phenylindenes were synthesized from their corresponding methoxy-substituted 3,4-diphenylhexane-3,4-diols by cyclization with acetyl chloride and acetic anhydride and subsequent ether cleavage and acetylation. In this series, the 2-phenylindene derivative (compound 13) with a 5,6,3',4'-tetraacetoxy and a 1-methyl-3-ethyl substitution had the highest affinity for the estrogen receptor, the strongest antiestrogenic effect, and the lowest estrogenic effect. This compound was superior to the 2-phenylindenes with 5,3'-diacetoxy substitution or 1,1-dimethyl and 3-isopropyl moieties, respectively. Compound 13 exhibited a strong, significant inhibiting effect on the growth of the hormone-dependent MXT mouse mammary tumor without estrogenic side effects.

  DOI：

  10.1021/jm00151a012