18-iodocortisol acetonide | 144268-70-2

• 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: 18-iodocortisol acetonide
• 英文别名: 11β-hydroxy-18-iodo-17α,21-isopropylidenedioxypregn-4-ene-3,20-dione；(4R,8'S,9'S,10'R,11'S,13'R,14'S)-11'-hydroxy-13'-(iodomethyl)-2,2,10'-trimethylspiro[1,3-dioxane-4,17'-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene]-3',5-dione
• CAS: 144268-70-2
• 化学式: C₂₄H₃₃IO₅
• 分子量: 528.428
• InChiKey: ASEBWHUHSZEPLP-BGMBDRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  18-iodocortisol acetonide 在 jones reagent 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.33h， 以82%的产率得到18-iodo-17α,21-isopropylidenedioxypregn-4-ene-3,11,20-trione
  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
• 作为产物：
  描述：

  17α,21-(Dimethyl-methylendioxy)-Δ⁴-pregnenol-(11β)-dion-(3,20) 在 lead(IV) acetate 、 碘 、 calcium carbonate 作用下， 以 环己烷 、 苯 为溶剂， 反应 2.0h， 以75%的产率得到18-iodocortisol acetonide
  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

文献信息

• A simple synthesis of 11,19-oxidosteroids
  作者：Ahmed Boudi、Anne Zaparucha、Hervé Galons、Mohamed Chiadmi、Bernard Viossat、Alain Tomas、Jean Fiet

  DOI：10.1016/0039-128x(94)00075-n

  日期：1995.5

  The photochemical hypoiodination of cortisol acetonide gave a mixture of 18-iodocortisol acetonide and of the 11 beta,19-oxidoderivative. The proportion of the two products was slightly modified by the reaction temperature. Deprotection of the acetonide group of the 11 beta,19-oxidoderivative gave 11 beta,19-oxido-17 alpha,21-dihydroxy-4-pregnen-3,20-dione which led to the formation of 11 beta,19-oxido-4-androsten-3,17-dione upon treatment with sodium bismutate.