N-butyl, N-methyl-11-(3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-undecanamide | 138743-10-9

• 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
• 英文名称: N-butyl, N-methyl-11-(3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-undecanamide
• 英文别名: N-butyl-11-[(8R,9S,13S,14S,17S)-17-hydroxy-3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-15-yl]-N-methylundecanamide
• CAS: 138743-10-9；138743-23-4
• 化学式: C₃₅H₅₇NO₃
• 分子量: 539.842
• InChiKey: FFLAHJPVFDPNCJ-UJRYTYLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  39.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-butyl, N-methyl-11-(3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-undecanamide 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以65%的产率得到N-butyl, N-methyl-11-(3',17'β-dihydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-undecanamide
  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
• 作为产物：
  描述：

  3-methoxy-estra-1,3,5(10),15-tetraen-17-one 在 sodium tetrahydroborate 、 三正丁胺 、 铬酸 、 potassium carbonate 、 对甲苯磺酸 、 氯甲酸异丁酯 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 9.67h， 生成 N-butyl, N-methyl-11-(3'-methoxy-17'β-hydroxy-1',3',5'(10')-estratriene-15'(α,β)-yl)-undecanamide
  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