3β-hydroxy-5β,19-cyclo-6-androstene-17S-spiro-oxirane | 69269-56-3

• 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: 3β-hydroxy-5β,19-cyclo-6-androstene-17S-spiro-oxirane
• CAS: 69269-56-3
• 化学式: C₂₀H₂₈O₂
• 分子量: 300.441
• InChiKey: QVZBDMBAFOXCJT-KKVRMWHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  32.76
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-5β,19-cyclo-6-androstene-17S-spiro-oxirane 在 对甲苯磺酸 作用下， 生成 ethyl (((3S,5S,8R,9S,10S,13S,14S,17S)-3,17-dihydroxy-13-methyl-1,2,3,4,8,9,12,13,14,15,16,17-dodecahydro-11H-5,10-methanocyclopenta[a]phenanthren-17-yl)methyl)(methyl)carbamate
  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：

  三甲基碘化锍 、 3β-acetoxy-5β,19-cyclo-6-androstene-17-one 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 以50%的产率得到3β-hydroxy-5β,19-cyclo-6-androstene-17S-spiro-oxirane
  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