15β,17α-dihydroxy-5β-pregnan-3,20-dione | 171980-20-4

• 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: 15β,17α-dihydroxy-5β-pregnan-3,20-dione
• CAS: 171980-20-4
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: FQWSHRSEWLUENX-SLHRYYKLSA-N

物化性质

• 沸点：
  503.4±50.0 °C(Predicted)
• 密度：
  1.184±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  25.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  74.6
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  15β,17α-dihydroxy-5β-pregnan-3,20-dione 在 sodium tetrahydroborate 作用下， 生成 (3α,5β,15β)-3,15,17-三羟基孕烷-20-酮
  参考文献：
  名称：

  15β-hydroxysteroids (Part V). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20-one from 15β, 17α-dihydroxy-4-pregnen-3,20-dione

  摘要：

  A simple three-step synthetic method is reported on the conversion of Delta(4)-3-ketosteroids to the corresponding 3 beta-hydroxy-Delta(5)-steroid analogues. 17 alpha-Hydroxy-4-pregnen-3,20-dione (10a) was used as a model to develop a method for the synthesis of 3 beta, 17 alpha-dihydroxy-5-pregnen-20-one (16). The major problem being the synthesis of 3,17 alpha-diacetoxy-3,5-pregnadien-20-one(14) was solved by acetylating using a mixture of acetic anhydride and perchloric acid. The conversion of 15 beta, 17 alpha-dihydroxy-4-pregnen-3,20-dione (8), product of Penicillium citrinum fermentation, to the desired 3 beta,15 beta 17 alpha-trihydroxy-5-pregen-20-one (1), is described using a modification of this method. Reaction of 8 with acetic anhydride and perchloric acid in ethyl acetate gave 3, 15 beta,17 alpha-triacetoxy-3,5-pregnadien-20-one (17) which on reduction with sodium borohydride gave 5-pregnen-3 beta,15 beta,17 alpha,20(S + R)-tetrols (18a and 18b); however, reduction of 17 with a mixture of sodium borohydride and potassium bicarbonate gave after basic hydrolysis with methanolic sodium hydroxide the desired product 3 beta, 15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1) in good yield (54%).

  DOI：

  10.1016/0039-128x(95)00170-u
• 作为产物：
  描述：

  15β,17α,21-trihydroxy-4-pregnen-3,20-dione 在 Lindlar's catalyst 氢气 、 sodium iodide 、 锌 作用下， 生成 15β,17α-dihydroxy-5β-pregnan-3,20-dione
  参考文献：
  名称：

  15β-hydroxysteroids (Part V). Steroids of the human perinatal period: The synthesis of 3β, 15β, 17α-trihydroxy-5-pregnen-20-one from 15β, 17α-dihydroxy-4-pregnen-3,20-dione

  摘要：

  A simple three-step synthetic method is reported on the conversion of Delta(4)-3-ketosteroids to the corresponding 3 beta-hydroxy-Delta(5)-steroid analogues. 17 alpha-Hydroxy-4-pregnen-3,20-dione (10a) was used as a model to develop a method for the synthesis of 3 beta, 17 alpha-dihydroxy-5-pregnen-20-one (16). The major problem being the synthesis of 3,17 alpha-diacetoxy-3,5-pregnadien-20-one(14) was solved by acetylating using a mixture of acetic anhydride and perchloric acid. The conversion of 15 beta, 17 alpha-dihydroxy-4-pregnen-3,20-dione (8), product of Penicillium citrinum fermentation, to the desired 3 beta,15 beta 17 alpha-trihydroxy-5-pregen-20-one (1), is described using a modification of this method. Reaction of 8 with acetic anhydride and perchloric acid in ethyl acetate gave 3, 15 beta,17 alpha-triacetoxy-3,5-pregnadien-20-one (17) which on reduction with sodium borohydride gave 5-pregnen-3 beta,15 beta,17 alpha,20(S + R)-tetrols (18a and 18b); however, reduction of 17 with a mixture of sodium borohydride and potassium bicarbonate gave after basic hydrolysis with methanolic sodium hydroxide the desired product 3 beta, 15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1) in good yield (54%).

  DOI：

  10.1016/0039-128x(95)00170-u

文献信息

• 15β-hydroxysteroids (Part IV). Steroids of the human perinatal period: The synthesis of 3α,15β,17α-trihydroxy-5α-pregnan-20-one and its AB-ring configurational isomers
  作者：Anthony Y. Reeder、George E. Joannou

  DOI：10.1016/0039-128x(95)00142-d

  日期：1995.12

  20-one (11), a product of chemical synthesis was converted to the isomeric 3 and 7, while conversion of 15 beta,17 alpha-dihydroxy-4-pregnen-3,20-dione (4), a product of microbiological transformation, resulted in the preparation of 8. In brief, selective acetate hydrolysis of 11 gave 15 beta-acetoxy-3 beta,17 alpha-dihydroxy-5-pregnen-20-one (12) which on catalytic hydrogenation gave 15 beta-acetoxy-3

  近年来，在人类新生儿中出现了数种15种β-羟类固醇对肾上腺疾病的致病性，其中3个alpha，15 beta，17 alpha-trihydroxy-5 beta-pregnan-20-one（2）在尿液中首次被发现先天性肾上腺皮质增生症的新生儿 在这项研究中，我们报告了剩余的3种xi，5个xi-异构体的合成，即3 alpha，15 beta，17 alpha-trihydroxy-5 alpha-pregnan-20-one（3），3 beta，15 beta，17 alpha-trihydroxy-5 alpha-pregnan-20-one（7）和3 beta，15 beta，17 alpha-trihydroxy-5 beta-pregnan-20-one（8）在人类新生儿病理状况中的确定性鉴定。3 beta，15 beta-Diacetoxy-17 alpha-hydroxy-5-