(8R,9S,10R,13S,14S,17S)-13-乙基-17-乙炔基-3-氧代-2,3,6,7,8,9,10,11,12,13,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基环丁烷羧酸酯 | 86679-36-9

• 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
• 中文名称: (8R,9S,10R,13S,14S,17S)-13-乙基-17-乙炔基-3-氧代-2,3,6,7,8,9,10,11,12,13,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基环丁烷羧酸酯
• 英文名称: D-(-)-norgestrel 17β-cyclobutanecarboxylate
• 英文别名: levonorgestrel 17β-cyclobutylcarboxylate；levonorgestrel cyclobutylcarboxylate；13-Ethyl-17alpha-hydroxy-18,19-dinorpregn-4-en-20-yn-3-one cyclobutanecarboxylate；[(8R,9S,10R,13S,14S,17R)-13-ethyl-17-ethynyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] cyclobutanecarboxylate
• CAS: 86679-36-9
• 化学式: C₂₆H₃₄O₃
• 分子量: 394.554
• InChiKey: WWGTWFPUIPEHNX-UKNJCJGYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  左炔诺孕酮 、 环丁基甲酰氯 在 thallium (I) ethoxide 作用下， 生成 (8R,9S,10R,13S,14S,17S)-13-乙基-17-乙炔基-3-氧代-2,3,6,7,8,9,10,11,12,13,14,15,16,17-十四氢-1H-环戊二烯并[a]菲-17-基环丁烷羧酸酯
  参考文献：
  名称：

  Long-acting contraceptive agents: Design of the who chemical synthesis programme

  摘要：

  The great demand for improved long-acting injectable steroid contraceptives, particularly in developing countries, and the relative lack of interest from the pharmaceutical industry to develop such products stimulated WHO to launch a synthetic and screening programme to find improved, safe and acceptable injectable preparations. More than 210 esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) and levonorgestrel (D-(-)-13 beta-ethyl-17 alpha-ethynyl-17 beta-hydroxygon-4-en-3-one) have been prepared in university-based research laboratories situated mainly in developing countries, and then screened by NICHHD in animal models. The following three compounds, levonorgestrel butanoate, cyclopropylcarboxylate and cyclobutylcarboxylate, proved to be particularly long-acting when administered as microcrystalline suspensions. The overall strategy of this research and development programme is described.

  DOI：

  10.1016/0039-128x(83)90095-8

文献信息

• Norethisterone and levonorgestrel esters: A novel synthetic method
  作者：S.L. Leung、R. Karunanithy、G. Becket、S.H. Yeo

  DOI：10.1016/0039-128x(85)90027-3

  日期：1985.7

  Aliphatic, alicyclic and arylcarboxylic esters of norethisterone and levonorgestrel were prepared in a one-step synthesis and in near-quantitative yield using trifluoroacetic anhydride.
• Long-acting contraceptive agents: Design of the who chemical synthesis programme
  作者：Pierre Crabbé、Sydney Archer、Giuseppe Benagiano、Egon Diczfalusy、Carl Djerassi、Josef Fried、Takeru Higuchi

  DOI：10.1016/0039-128x(83)90095-8

  日期：1983.3

  The great demand for improved long-acting injectable steroid contraceptives, particularly in developing countries, and the relative lack of interest from the pharmaceutical industry to develop such products stimulated WHO to launch a synthetic and screening programme to find improved, safe and acceptable injectable preparations. More than 210 esters of norethisterone (17 alpha-ethynyl-17 beta-hydroxyestr-4-en-3-one) and levonorgestrel (D-(-)-13 beta-ethyl-17 alpha-ethynyl-17 beta-hydroxygon-4-en-3-one) have been prepared in university-based research laboratories situated mainly in developing countries, and then screened by NICHHD in animal models. The following three compounds, levonorgestrel butanoate, cyclopropylcarboxylate and cyclobutylcarboxylate, proved to be particularly long-acting when administered as microcrystalline suspensions. The overall strategy of this research and development programme is described.