N-butyl, N-methyl-9-(3',17'β-dihydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-nonamide | 138743-01-8

• 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: N-butyl, N-methyl-9-(3',17'β-dihydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-nonamide
• 英文别名: N-butyl-9-[(8R,9S,13S,14S,17S)-3,17-dihydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-15-yl]-N-methylnonanamide
• CAS: 138743-01-8；138743-24-5
• 化学式: C₃₂H₅₁NO₃
• 分子量: 497.762
• InChiKey: YTPJDBMCZRXXFB-BSJLBJFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  60.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基丁胺 在 palladium on activated charcoal sodium tetrahydroborate 、 三正丁胺 、 氢气 、 氯甲酸异丁酯 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， -10.0~25.0 ℃ 、101.33 kPa 条件下， 反应 28.67h， 生成 N-butyl, N-methyl-9-(3',17'β-dihydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-nonamide
  参考文献：
  名称：

  Synthesis of 17β-estradiol derivatives with n-butyl, n-methyl alkylamide side chain at position 15

  摘要：

  New derivatives of 17-beta-estradiol with N-butyl, N-methyl alkylamide side chains of three different lengths at position 15 have been synthesized from estrone. Compounds 5 and 6 having a shorter alkylamide chain were obtained in eleven steps by introduction of a 15, 16 double bond followed by an 1, 4 addition of alkylcopper reagent and further transformations including hydrolysis, Jones' oxidation, amidation, reduction and cleavage of the protective group. Compound 7 having the longest alkylamide chain was synthesized by chain lengthening (five additional steps) of an intermediate obtained in the course of synthesis of compound 6.

  DOI：

  10.1016/s0040-4020(01)81933-5

文献信息

• Synthesis of 17β-estradiol derivatives with n-butyl, n-methyl alkylamide side chain at position 15
  作者：Donald Poirier、Yves Mérand、Fernand Labrie

  DOI：10.1016/s0040-4020(01)81933-5

  日期：1991.9

  New derivatives of 17-beta-estradiol with N-butyl, N-methyl alkylamide side chains of three different lengths at position 15 have been synthesized from estrone. Compounds 5 and 6 having a shorter alkylamide chain were obtained in eleven steps by introduction of a 15, 16 double bond followed by an 1, 4 addition of alkylcopper reagent and further transformations including hydrolysis, Jones' oxidation, amidation, reduction and cleavage of the protective group. Compound 7 having the longest alkylamide chain was synthesized by chain lengthening (five additional steps) of an intermediate obtained in the course of synthesis of compound 6.