5-Beta- 孕烷-17,21-二醇-3,20-二酮 | 566-42-7

• 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: 5-Beta- 孕烷-17,21-二醇-3,20-二酮
• 中文别名: 5-Beta-孕烷-17,21-二醇-3,20-二酮
• 英文名称: 5β-pregnan-17α,21-diol-3,20-dione
• 英文别名: 5β-dihydro-11-deoxycortisol；5β-dihydro-Reichstein's S；17,21-dihydroxy-5β-pregnane-3,20-dione；17,21-Dihydroxy-5β-pregnan-3,20-dion；17.21-Dihydroxy-5β-pregnandion-(3.20)；5beta-Pregnan-17,21-diol-3,20-dione；(5R,8R,9S,10S,13S,14S,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-2,4,5,6,7,8,9,11,12,14,15,16-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 566-42-7
• 化学式: C₂₁H₃₂O₄
• 分子量: 348.483
• InChiKey: WNIBSYGPDJBVOA-BRRPRDELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.904
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Beta- 孕烷-17,21-二醇-3,20-二酮 在 sodium bismuthate 、 溶剂黄146 作用下， 生成 还原胆烷醇酮
  参考文献：
  名称：

  The Conversion of 17α,21-Dihydroxypregnane-3,20-dione to 3α,17α,21-Trihydroxypregnan-20-one in vitro^1,2

  摘要：

  DOI：

  10.1021/ja01633a095
• 作为产物：
  描述：

  5β-dihydro-11-deoxycortisol 21-acetate 在 甲醇 、 potassium hydrogencarbonate 作用下， 生成 5-Beta- 孕烷-17,21-二醇-3,20-二酮
  参考文献：
  名称：

  The Conversion of 17α,21-Dihydroxypregnane-3,20-dione to 3α,17α,21-Trihydroxypregnan-20-one in vitro^1,2

  摘要：

  DOI：

  10.1021/ja01633a095

文献信息

• Preparation of haptens for use in immunoassays of tetrahydro-11-deoxycortisol and its glucuronides.
  作者：HIROSHI HOSODA、HIROMITSU YOKOHAMA、KAZUO ISHII、YUKO ITO、TOSHIO NAMBARA

  DOI：10.1248/cpb.31.4001

  日期：——

  For the purpose of developing immunoassays of tetrahydro-11-deoxycortisol or its glucuronides, various haptenic derivatives were synthesized. The 3-hemisuccinate (15), 21-hemisuccinate (8), 3-hemiglutarate (16), 21-hemiglutarate (9) and glucuronides (19, 23, 25) of tetrahydro-11-deoxycortisol were prepared starting from 11-deoxycortisol 21-acetate (1). Then, antisera were elicited in two rabbits by immunization with the conjugate of tetrahydro-11-deoxycortisol 3-glucuronide (19) with bovine serum albumin. It was found that the antisera had binding affinities to enzyme-labeled antigens prepared from 15, 16 and 19 ; the binding was inhibited by the glucuronide (19) in the enzyme immunoassay procedure.

  为了开发四氢-11-脱氧皮质醇或其葡萄糖醛酸苷的免疫测定法，合成了各种半抗原衍生物。以11-脱氧皮质醇为原料制备四氢-11-脱氧皮质醇的3-半琥珀酸酯(15)、21-半琥珀酸酯(8)、3-半戊二酸酯(16)、21-半戊二酸酯(9)和葡萄糖醛酸苷(19,23,25) 21-乙酸盐(1)。然后，用四氢-11-脱氧皮质醇3-葡萄糖醛酸苷(19)与牛血清白蛋白的缀合物免疫两只兔子，以产生抗血清。发现该抗血清与15、16和19制备的酶标抗原具有结合亲和力；在酶免疫测定过程中，结合被葡萄糖醛酸苷 (19) 抑制。
• Chemical synthesis of 11-deoxycortisol metabolites.
  作者：HIROSHI HOSODA、HIROMITSU YOKOHAMA、HIROAKI SHIOYA、TOSHIO NAMBARA

  DOI：10.1248/cpb.33.1049

  日期：——

  The synthesis of the 3-glucuronides of 11-deoxycortisol metabolites is described. 3α, 17α, 20α-Trihydroxy-5β-pregnan-21-oic acid 3-glucuronide (13) and its 20β-epimer (14) were prepared starting from 5β-dihydro-11-deoxycortisol (1). The 20-acetoxy-21-oic acid methyl esters (7, 8) were the key intermediates. Oxidation of 1 with cupric acetate followed by the intramolecular Cannizzaro reaction gave the 20-epimeric 20-hydroxy-21-acids (5, 6), which, on methylation with diazomethane followed by acetylation, were converted into the acetate-methyl esters (3, 4). Reduction of the carbonyl group at C-3 in 3 and 4 with sodium borohydride gave the desired intermediates. Introduction of the glucuronyl residue at the C-3 position was carried out by means of the Koenigs-Knorr reaction. 20-Epimeric 5β-pregnane-3α, 17α, 20, 21-tetrol 3-glucuronides (26, 27) were also prepared.

  介绍了 11-脱氧皮质醇代谢物 3-葡萄糖醛酸的合成。3α，17α，20α-三羟基-5β-孕甾-21-酸 3-葡萄糖醛酸苷（13）及其 20β-epimer （14）是由 5β-二氢-11-脱氧皮质醇（1）开始制备的。20-acetoxy-21-oic acid methyl esters (7, 8) 是关键的中间体。1 与醋酸铜氧化，然后发生分子内 Cannizzaro 反应，生成 20-epimeric 20-hydroxy-21-acids (5, 6)。用硼氢化钠还原 3 和 4 中 C-3 处的羰基，可得到所需的中间体。通过柯尼希斯-克诺尔（Koenigs-Knorr）反应将葡萄糖醛酸残基引入 C-3 位。还制备出了 20-二聚体 5β-孕甾-3α，17α，20，21-四醇 3-葡萄糖醛酸（26，27）。
• Action of Some Steroids on the Central Nervous System of the Mouse. I. Synthetic Methods
  作者：J. D. Cocker、J. Elks、P. J. May、F. A. Nice、G. H. Phillipps、W. F. Wall

  DOI：10.1021/jm00328a003

  日期：1965.7
• Microbiological Transformations of Steroids. IV. The 11-Epimer of Compound F and Other New Oxygenated Derivatives of Reichstein's Compound S. A New Route to Cortisone¹
  作者：D. H. Peterson、S. H. Eppstein、P. D. Meister、B. J. Magerlein、H. C. Murray、H. Marian Leigh、A. Weintraub、L. M. Reineke

  DOI：10.1021/ja01098a045

  日期：1953.1