15β,17α,21-trihydroxy-4-pregnen-3,20-dione | 128947-84-2

• 英文名称: 15β,17α,21-trihydroxy-4-pregnen-3,20-dione
• 英文别名: 15β,17,21-trihydroxy-pregn-4-ene-3,20-dione；15β,17,21-Trihydroxy-pregn-4-en-3,20-dion；(8R,9S,10R,13S,14S,15R,17R)-15,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 128947-84-2
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: MQDCOPQEQANADS-ZJKUDWTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.78
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  94.83
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  脱氧可的松 生成 15β,17α,21-trihydroxy-4-pregnen-3,20-dione
  参考文献：
  名称：

  Bernstein et al., Chemistry and industry, 1956, p. 111

  摘要：

  DOI：

文献信息

• Herzog et al., Journal of Organic Chemistry, 1959, vol. 24, p. 691,694
  作者：Herzog et al.

  DOI：——

  日期：——
• C-15 Substituted Steroids. 15α- and 15β-Hydroxy-Reichstein's Substance S and Transformation Products
  作者：Seymour Bernstein、Milton Heller、Louis I. Feldman、William S. Allen、Robert H. Blank、Carl E. Linden

  DOI：10.1021/ja01499a053

  日期：1960.7
• KLIMOVA, L. I.;MALANINA, G. G.;FILIPENKO, T. YA.;TURCHIN, K. F., XIM.-FARMATS. ZH., 23,(1989) N, S. 1122-1124
  作者：KLIMOVA, L. I.、MALANINA, G. G.、FILIPENKO, T. YA.、TURCHIN, K. F.

  DOI：——

  日期：——