(8R,9S,13S,14S,16R,17R)-3,16,17-trihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-4-carbaldehyde | 1336906-94-5

• 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: (8R,9S,13S,14S,16R,17R)-3,16,17-trihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-4-carbaldehyde
• CAS: 1336906-94-5
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: KEYCBGDXAXFTFB-YBKSATHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 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：
  0.63
• 拓扑面积：
  77.76
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 雌三醇 在 三乙胺 、 magnesium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 (8R,9S,13S,14S,16R,17R)-3,16,17-trihydroxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-4-carbaldehyde 、 3,16a,17β-trihydroxyestra-1,3,5(10)-triene-2-carbaldehyde
  参考文献：
  名称：

  ortho-Formylation of estrogens. Synthesis of the anti-cancer agent 2-methoxyestradiol

  摘要：

  Several estrogens were mono-formylated using a mixture of paraformaldehyde. MgCl2, and Et3N in refluxing THF. In all cases, the 2-isomer was formed as the major product with high regioselectivity compared to the 4-isomer. Excellent to high yields were obtained in all examples except one. The method was applied for an efficient synthesis of the anti-cancer agent 2-methoxyestradiol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.005