2-hydroxyestriol 3-methylether | 28818-82-8

• 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: 2-hydroxyestriol 3-methylether
• 英文别名: 2-Hydroxy-oestriol-3-methylether；(8R,9S,13S,14S,16R,17R)-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2,16,17-triol
• CAS: 28818-82-8
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: KVPGEQWOSKQRRJ-YSYMNNNUSA-N

物化性质

• 熔点：
  268-271 °C(Solv: methanol (67-56-1); benzene (71-43-2))
• 沸点：
  486.4±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  23.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  69.92
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-hydroxyestriol 3-methylether 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 2-羟基雌三醇
  参考文献：
  名称：

  Water-soluble metabolites of the estrogens. Quantitation of C-18 tetrols in rat feces

  摘要：

  Several radioactive estrogens possessing one, two and three hydroxyl groups were injected orally (and in the case of estrone sulfate also intraperitoneally) into adult male rats. The rats were either intact or had ligated or cannulated bile ducts. Two unconjugated estrogen tetrols together represented 21 - 87% of the total metabolites in the intact rat. One of the tetrols was 2-hydroxyestriol (estra-1,3,5(10)-triene-2,3,16alpha,17beta-tetrol); the other may be estra-1,3,5(10)-triene-2,3,6xi,17beta-tetrol but this was not confirmed. It is concluded that poly-hydroxylated estrogens represent a very large proportion of the previously unidentified water-soluble metabolites of the estrogens in the adult male rat.

  DOI：

  10.1016/0039-128x(76)90055-6
• 作为产物：
  描述：

  2-Hydroxy-oestriol-3-methylether-16,17-diacetat 在 氢氧化钾 作用下， 生成 2-hydroxyestriol 3-methylether
  参考文献：
  名称：

  Catechol Derivatives of Estrogens¹

  摘要：

  DOI：

  10.1021/jo01074a026

文献信息

• New synthesis of 2-hydroxyestrogen 2-monoglucuronides.
  作者：TADASHI OHKUBO、FUMIKO TSUCHIKO、TOSHIO NAMBARA

  DOI：10.1248/cpb.36.419

  日期：——

  New synthetic routes leading to catechol estrogen 2-monoglucuronides are described. Selective introduction of a glucuronyl residue into the C-2 hydroxyl group was undertaken by utilizing a steric interaction of the 3-hydroxyl group with a bulky substituent at C-4. For this purpose, 4-bromo-2-hydroxyestriol 16, 17-diacetate was used as a key intermediate. The Koenigs-Knorr reaction of this catechol with methyl α-acetobromoglucuronate in the presence of cadmium carbonate proceeded preferentially toward the C-2 hydroxyl group. Subsequent reductive dehalogenation followed by alkaline hydrolysis provided the desired 2-hydroxyestriol 2-glucuronide. In a similar fashion, 2-hydroxyestradiol and-2-hydroxyestrone 2-glucuronides were also prepared.

  本文描述了合成儿茶酚雌激素 2-葡萄糖醛酸单酯的新合成路线。通过利用 3-羟基基团与 C-4 处大体积取代基的空间相互作用，选择性地将葡萄糖醛酸残基引入 C-2 羟基基团。为此，4-溴-2-羟基雌三醇 16,17-二乙酸酯被用作关键中间体。在碳酸镉存在下，儿茶酚与甲基 α-乙酰溴葡萄糖醛酸酯的 Koenigs-Knorr 反应优先朝向 C-2 羟基基团进行。随后的还原脱卤和碱性水解反应提供了所需的 2-羟基雌三醇 2-葡萄糖醛酸单酯。以类似的方式，2-羟基雌二醇和 2-羟基雌酮 2-葡萄糖醛酸单酯也可以制备。