(8R,9S,13S,14S,17S)-13-ethyl-3-methoxy-1,4,6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,5'-oxazolidin]-2'-one | 69269-42-7

• 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: (8R,9S,13S,14S,17S)-13-ethyl-3-methoxy-1,4,6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,5'-oxazolidin]-2'-one
• CAS: 69269-42-7
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: FGUFODGRXAAZHI-PIBZIWMISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.71
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (8R,9S,13S,14S,17S)-13-ethyl-3-methoxy-1,4,6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,5'-oxazolidin]-2'-one 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以48%的产率得到(8R,9S,10R,13S,14S,17S)-13-ethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,5'-oxazolidine]-2',3(2H)-dione
  参考文献：
  名称：

  Synthesis of new spiro-steroids, II: Steroid-17-spiro-oxazolidinones*1

  摘要：

  New, potential aldosterone blocking 17-spiro-oxazolidinone derivatives with androstane, estrane and 13 beta-ethyl-gonane ring system were synthesized. 17S-Spiro-oxiranes were used as starting compounds and the oxazolidinone ring was built up in different ways. All compounds but one were devoid of considerable endocrine activities. 3-Oxo-13 beta-ethyl-gona-4,9(10),11-triene-17S-spiro-5'-(2'-oxo-3'-methyl)oxazolidine shows significant antiandrogen activity on s.c., but none on p.o. administration.

  DOI：

  10.1016/0039-128x(80)90138-5
• 作为产物：
  描述：

  13β-ethyl-3-methoxy-gona-2,5(10)-diene-17S-spiro-oxirane 、 氨基甲酸乙酯 在 potassium tert-butylate 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 13.0h， 以42%的产率得到(8R,9S,13S,14S,17S)-13-ethyl-3-methoxy-1,4,6,7,8,9,11,12,13,14,15,16-dodecahydrospiro[cyclopenta[a]phenanthrene-17,5'-oxazolidin]-2'-one
  参考文献：
  名称：

  Synthesis of new spiro-steroids, II: Steroid-17-spiro-oxazolidinones*1

  摘要：

  New, potential aldosterone blocking 17-spiro-oxazolidinone derivatives with androstane, estrane and 13 beta-ethyl-gonane ring system were synthesized. 17S-Spiro-oxiranes were used as starting compounds and the oxazolidinone ring was built up in different ways. All compounds but one were devoid of considerable endocrine activities. 3-Oxo-13 beta-ethyl-gona-4,9(10),11-triene-17S-spiro-5'-(2'-oxo-3'-methyl)oxazolidine shows significant antiandrogen activity on s.c., but none on p.o. administration.

  DOI：

  10.1016/0039-128x(80)90138-5