17β-(2-methoxyethylamino)estra-1,3,5(10)-triene-3,16α-diol | 244622-97-7

• 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: 17β-(2-methoxyethylamino)estra-1,3,5(10)-triene-3,16α-diol
• 英文别名: (8R,9S,13S,14S,16R,17R)-17-(2-methoxyethylamino)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16-diol
• CAS: 244622-97-7
• 化学式: C₂₁H₃₁NO₃
• 分子量: 345.482
• InChiKey: XIGQIFVRBJNGFQ-YQPXSLGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  61.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17β-(2-methoxyethylamino)estra-1,3,5(10)-triene-3,16α-diol 在 sodium tetrahydroborate 、 jones reagent 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 0.66h， 生成 17β-(2-methoxyethylamino)estra-1,3,5(10)-triene-3,16β-diol
  参考文献：
  名称：

  Structure of the adduct of 16α-hydroxyestrone with a primary amine: evidence for the heyns rearrangement of steroidal D-ring α-hydroxyimines

  摘要：

  16-alpha-Hydroxyestrone, a product of estrogen 16-alpha-hydroxylation in humans that is suspected to be implicated in cell transformation, has been found to form stable adducts with nuclear components. The stable covalent adduct formed from 16-alpha-hydroxyestrone with 2-methoxyethylamine via the Heyns rearrangement of the alpha-hydroxyimine was identified as 3-hydroxy-17-beta-(2-methoxyethylamino)estra-1,3,5(10)-trien-16-one. Since the same product was obtained from 16-beta-hydroxyestrone with the amine, the alpha-hydroxyenamine is the most likely intermediate of the Heyns rearrangement. The adduct was fairly stable at 37 C in phosphate buffer (pH 7.4)/methanol (1:1 v/v), while the adduct formed from 16-oxoestradiol was disrupted reversely and completely within 6 hours. The evidence suggests that N-(3-hydroxy-16-oxoestra-1,3,5(10)-trien-17-beta-yl)amine is the partial structure of the stable adducts formed from D-ring alpha-ketol estrogens with proteins.

  DOI：

  10.1016/0039-128x(91)90068-7
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 26.33h， 生成 17β-(2-methoxyethylamino)estra-1,3,5(10)-triene-3,16α-diol
  参考文献：
  名称：

  Structure of the adduct of 16α-hydroxyestrone with a primary amine: evidence for the heyns rearrangement of steroidal D-ring α-hydroxyimines

  摘要：

  16-alpha-Hydroxyestrone, a product of estrogen 16-alpha-hydroxylation in humans that is suspected to be implicated in cell transformation, has been found to form stable adducts with nuclear components. The stable covalent adduct formed from 16-alpha-hydroxyestrone with 2-methoxyethylamine via the Heyns rearrangement of the alpha-hydroxyimine was identified as 3-hydroxy-17-beta-(2-methoxyethylamino)estra-1,3,5(10)-trien-16-one. Since the same product was obtained from 16-beta-hydroxyestrone with the amine, the alpha-hydroxyenamine is the most likely intermediate of the Heyns rearrangement. The adduct was fairly stable at 37 C in phosphate buffer (pH 7.4)/methanol (1:1 v/v), while the adduct formed from 16-oxoestradiol was disrupted reversely and completely within 6 hours. The evidence suggests that N-(3-hydroxy-16-oxoestra-1,3,5(10)-trien-17-beta-yl)amine is the partial structure of the stable adducts formed from D-ring alpha-ketol estrogens with proteins.

  DOI：

  10.1016/0039-128x(91)90068-7