15β,17-dihydroxyprogesterone | 71118-02-0

• 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,17-dihydroxyprogesterone
• 英文别名: 15β,17α-dihydroxy-4-pregnen-3,20-dione；15,17-Dihydroxyprogesterone；(8R,9S,10R,13S,14S,15R,17R)-17-acetyl-15,17-dihydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 71118-02-0
• 化学式: C₂₁H₃₀O₄
• 分子量: 346.467
• InChiKey: FWKZKCGCFQKDQY-KCTPXNJMSA-N

物化性质

• 熔点：
  213-215 °C
• 沸点：
  523.9±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  15β,17-dihydroxyprogesterone 在 Lindlar's catalyst 氢气 、 L-Selectride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 2.0h， 生成 (3α,5β,15β)-3,15,17-三羟基孕烷-20-酮
  参考文献：
  名称：

  15种β-羟基类固醇（第四部分）。人类围产期的类固醇：3 alpha，15 beta，17 alpha-trihydroxy-5 alpha-pregnan-20-one及其A / B环构型异构体的合成。

  摘要：

  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-

  DOI：

  10.1016/0039-128x(95)00142-d
• 作为产物：
  描述：

  脱氧可的松 在 sodium iodide 、 锌 作用下， 生成 15β,17-dihydroxyprogesterone
  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

• Tanabe et al., Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 811,815
  作者：Tanabe et al.

  DOI：——

  日期：——
• Chick oviduct progesterone receptor binding of 15β,17-dihydroxyprogesterone and its analogues
  作者：Michael E. Baker、Trevor C. McMorris、Linda S. Terry、Susan E. Barrow、Diana L. Villanueva

  DOI：10.1016/0039-128x(84)90034-5

  日期：1984.2

  We have tested derivatives of progesterone obtained by fermentation with Aspergillus giganteus for relative binding affinity for the progesterone receptor of chick oviduct. Our studies show that hydroxyl and oxo substitutents at C-11 and C-15 of progesterone significantly decrease the hormone's affinity for the progesterone receptor. The loss in affinity on introduction of a C-15 hydroxyl in 17-hydroxyprogesterone is restored by acetylation to 15 beta-acetoxy-17 hydroxyprogesterone. The latter compound may have some potential as an in vivo agent.
• 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.
• 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
  作者：George E. Joannon、Anthony Y. Reeder

  DOI：10.1016/0039-128x(95)00170-u

  日期：1996.1

  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%).
• 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-