18-羟基皮质醇(半缩醛) | 144302-17-0

• 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: 18-羟基皮质醇(半缩醛)
• 英文名称: 18,20-epoxy-11β,17α,20β,21-tetrahydroxypregn-4-ene-3-one
• 英文别名: Pregn-4-ene-3,20-dione, 11,17,18,21-tetrahydroxy-, (11beta)-；(1S,2S,5R,6R,9S,11S,12S,13R)-5,6,11-trihydroxy-6-(hydroxymethyl)-13-methyl-7-oxapentacyclo[10.8.0.02,9.05,9.013,18]icos-17-en-16-one
• CAS: 144302-17-0
• 化学式: C₂₁H₃₀O₆
• 分子量: 378.466
• InChiKey: TZHBCIMMSKGBFX-PWAYDTSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  18,20-epoxy-11β,20β-dihydroxy-17α,21-isopropylidenedioxypregn-4-en-3-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以89.5%的产率得到18-羟基皮质醇(半缩醛)
  参考文献：
  名称：

  Convenient synthesis of 18-hydroxylated cortisol and prednisolone

  摘要：

  18,20-Epoxy-11-beta,17-alpha,20-beta,21-tetrahydroxypregn-4-en-3-one was synthesized by the application of hypoiodite reaction to the cortisol acetonide. The intermediary 18-iodo derivative was converted to the 11-oxo steroid by chromic acid prior to silver ion-assisted solvolysis. Removal of the protective group with hydrochloric acid was finally carried out to give the desired 11-beta,17-alpha,18,21-tetrahydroxypregn-4-ene-3,20-dione as the hemiacetal form. 18,20-Epoxy-11-beta-17-alpha,20-beta,21-tetrahydroxypregna-1,4-dien-3-one was also prepared from prednisolone through a similar reaction sequence.

  DOI：

  10.1016/0039-128x(92)90095-q