(3α,5β,15β)-3,15,17-三羟基孕烷-20-酮 | 80380-41-2

• 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
• 中文名称: (3α,5β,15β)-3,15,17-三羟基孕烷-20-酮
• 英文名称: 3α,15β,17α-trihydroxy-5β-pregnan-20-one
• 英文别名: 3,15,17-Trihydroxypregnan-20-one；1-[(3R,5R,8R,9S,10S,13S,14S,15R,17R)-3,15,17-trihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 80380-41-2
• 化学式: C₂₁H₃₄O₄
• 分子量: 350.499
• InChiKey: AIEUQVDPBZPTSV-VSAGWDKDSA-N

物化性质

• 沸点：
  504.6±50.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基胺盐酸盐 、 (3α,5β,15β)-3,15,17-三羟基孕烷-20-酮 在 吡啶 作用下， 反应 1.5h， 生成
  参考文献：
  名称：

  类固醇被21-羟化酶缺乏症的新生儿排泄在尿液中：使用GC-MS和GC-MS / MS表征孕烷和孕烷的D环和侧链结构。

  摘要：

  缺乏21-羟化酶的新生儿尿液中的类固醇代谢物主要是多羟基化的17-羟孕酮和雄激素代谢物，大多数结构不完全明确。这项研究是表征和鉴定这些特征的综合项目的一部分，以增强诊断并进一步阐明新生儿类固醇代谢的类型。在萃取和酶促共轭水解后，类固醇以甲基肟-三甲基甲硅烷基醚衍生物的形式在与四极杆和离子阱质谱仪联用的气相色谱仪上进行分析。在恒定激发条件下获得的GC-MS和GC-MS / MS光谱一起用于确定D-环和20-羟基和20-羟基孕烯（烯）的侧链的结构，这些烯基上没有氧基。 A环，B环和C环。考虑了D形环和侧链构型的所有可能组合。通过与氘代衍生物和硼氢化物还原的代谢物的光谱比较，可以将大多数片段解释为部分或完全的D环裂解，并丢失了侧链。还讨论了可能的重排离子。鉴定了140多种内源性代谢物。GC-MS / MS对于表征具有16,17-二羟基-20-氧代结构的化合物特别有用，该结构被解释为子宫内酶诱导的

  DOI：

  10.1016/j.steroids.2009.09.011
• 作为产物：
  描述：

  脱氧可的松 在 Lindlar's catalyst sodium tetrahydroborate 、 氢气 、 sodium iodide 、 锌 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

文献信息

• 15β-Hydroxysteroids (Part II). Steroids of the human perinatal period: The synthesis of 3α,15β,17α-trihydroxy-5β-pregnan-20-one
  作者：George E. Joannou、Anthony Y. Reeder

  DOI：10.1016/0039-128x(95)00194-u

  日期：1996.2

  Abstract Steroids hydroxylated at C-15 have long provided useful information about the well-being of the fetus and feto-placental unit in human pregnancy. In an attempt to develop a new and reliable imunoassay method for use in newborn screening programs for congenital adrenal hyperplasia, we report the chemical synthesis of 3α,15β,17α-trihydroxy-5β-pregnan-20-one (2) from 3α-hydroxy-5β-androstan-17-one

  摘要 C-15 羟基化的类固醇长期以来一直提供有关人类怀孕期间胎儿和胎儿胎盘单位健康的有用信息。为了开发一种用于先天性肾上腺增生的新生儿筛查项目的新的可靠免疫测定方法，我们报告了 3α-羟基的 3α,15β,17α-trihydroxy-5β-pregnan-20-one (2) 的化学合成-5β-androstan-17-one (4) 分 9 个步骤。简而言之，3α-hydroxy-5β-androst-15-en-17-one (6)，是通过苯基硒化从 4 中获得的，产生 3α-hydroxy-16α-phenylseleno-5β-androstan-17-one (5a)，其脱氢硒化得到 6. 通过加入 2-lithio-2-methyl-1,3-dithiane 然后酸催化重排得到 20,20-trimethylenedithio-5β-pregn 来引入 15β-羟基和侧链-16-en-3α
• 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-
• 15β-hydroxysteroids (part VII). Steroids of the human perinatal period: The synthesis of steroid markers and their radioactive tracers
  作者：Anthony Y. Reeder、George E. Joannou

  DOI：10.1016/s0039-128x(96)00204-8

  日期：1997.2

  We report the synthesis of 10 novel steroids obtained from 3 beta,15 beta-diacetoxy-17 alpha-hydroxy-5-pregnen-20-one (1c) as intermediates in the synthesis of 15 beta-acetoxy-2,20-ethylenedioxy-17 alpha-hydroxy-4-pregnen-3-one (6a) and its tritiated tracer 15 beta-acetoxy-20,20-ethylenedioxy-17 alpha-hydroxy-1,2,6,7-H-3-pregn-4-en-3-one (6d). The one pot interconversion of intermediate (6a) to 3 beta,15 beta,17 alpha-trihydroxy-5-pregnen-20-one (1a) and 3 alpha,15 beta,17 alpha-trihydroxy-5 beta-pregnan-20-one (2a) provides a new and efficient approach to the synthesis of diagnostically important metabolites of the human neonate and a possible route in the synthesis of the tritated tracers 3 beta,15 beta,17 alpha-trihydroxy-1,2,7-H-3-pregn-5-en-20-one (1d) and 3 alpha,15 beta,17 alpha-trihydroxy-1,2,6,7-H-3-5 beta-pregnan-20-one (2b) for the development of new immunoassays. We also report in this investigation an alternative route in the synthesis of 15 beta,17 alpha-dihydroxy-4-pregnen-3,20-dione (7a) an intermediate in the synthesis of human 15 beta-hydroxysteroid metabolites. (C) 1997 by Elsevier Science Inc.