(20R)-pregnadiene-(5,16)-diol-(3β,20) | 83509-40-4

• 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: (20R)-pregnadiene-(5,16)-diol-(3β,20)
• 英文别名: (20R)-Pregnadien-(5,16)-diol-(3β,20)；Pregnadien-(5,16)-diol-(3β,20β_F)；3β-Hydroxy-10,13-dimethyl-17-((R)-1-hydroxy-aethyl)-gonadien-(5,16)；(10R)-3c-Hydroxy-10r,13c-dimethyl-17-((R)-1-hydroxy-aethyl)-(8cH,9tH,14tH)-Δ^5,16-dodecahydro-1H-cyclopenta[a]phenanthren；5,16-Pregnadiene-3beta,20alpha-diol；(3S,8R,9S,10R,13S,14S)-17-[(1R)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 83509-40-4
• 化学式: C₂₁H₃₂O₂
• 分子量: 316.484
• InChiKey: AGHPIIDSYAFAJL-SWVQUTDYSA-N

物化性质

• 熔点：
  169-171 °C
• 沸点：
  455.6±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (20R)-pregnadiene-(5,16)-diol-(3β,20) 在 溶剂黄146 、 铂 作用下， 生成 3β,20β-Diacetoxy-5α-pregnan
  参考文献：
  名称：

  Butenandt; Schmidt-Thome, Chemische Berichte, 1939, vol. 72, p. 1960,1961

  摘要：

  DOI：
• 作为产物：
  描述：

  16-妊娠双烯醇酮 在 aluminum isopropoxide 、 异丙醇 作用下， 生成 (20R)-pregnadiene-(5,16)-diol-(3β,20)
  参考文献：
  名称：

  Hormone intermediates and preparation of same

  摘要：

  公开号：

  US02352648A1

文献信息

• Sterols. CXVII. Sapogenins. XLVI. The Structure of Pseudosapogenins
  作者：Russell E. Marker、D. L. Turner、R. B. Wagner、Paul R. Ulshafer、Harry M. Crooks、Eugene L. Wittle

  DOI：10.1021/ja01848a039

  日期：1941.3
• Kohout, Ladislav; Sanda, Vlastimil; Fajkos, Jan, Collection of Czechoslovak Chemical Communications, 1982, vol. 47, # 5, p. 1503 - 1513
  作者：Kohout, Ladislav、Sanda, Vlastimil、Fajkos, Jan

  DOI：——

  日期：——
• Synthesis and in vitro activity of some epimeric 20α-hydroxy, 20-oxime and aziridine pregnene derivatives as inhibitors of human 17α-hydroxylase/c 17,20 -lyase and 5α-reductase
  作者：Yang-zhi Ling、Ji-song Li、Katsuya Kato、Yang Liu、Xin Wang、Gregory T Klus、Kirk Marat、Ivo.P Nnane、Angela M.H Brodie

  DOI：10.1016/s0968-0896(98)00110-2

  日期：1998.10

  Some epimeric 20-hydroxy, 20-oxime, 16 alpha, 17 alpha-, 17,20- and 20,21-aziridine derivatives of progesterone were synthesized and evaluated as inhibitors of human 17 alpha-hydroxylase/C-17,C-20-lyase (P450(17 alpha)) and 5 alpha-reductase (5 alpha-R). The reduction of 16-dehydropregenolone acetate (3a) was reinvestigated. NaBH4 in the presence of CeCl3 gave better stereoselectivity for 20 beta-ol [20 alpha/20 beta-OH (4 alpha/4 beta)=1/2.7] than LTBAH or the Meerwein-Pondroff method reported; reduction with Zn in HOAc formed exclusively 20 alpha-ol (4 alpha b). The 20 alpha- and 20 beta-hydroxy-4,16-pregnadien-3-one (9 alpha) and (9 beta) were synthesized from the alcohols 4 alpha b and 4 beta b. Several 20-oxime pregnadienes and 16 alpha,17 alpha-, 17,20- and 20,21-aziridinyl-5-pregnene derivatives were also synthesized. LiAlH4 reduction of the 16-en-20-oxime (12b) yielded 20 (R)-(13a) and 20(S)-17 alpha,20-aziridine (13b) and 20(R)-17 beta,20-aziridine (14a). Several compounds inhibited the human P450(17 alpha) with greater potency than ketoconzole. The 5 alpha-R enzyme assay showed that while (9 alpha) did not have any activity, (9 beta) and (3b) were potent 5 alpha-reductase (IC50 = 21 and 31 nM) inhibitors with activities similar to finasteride. The 20-oximes (17a) and (17b) were potent dual inhibitors for both 5 alpha-R (IC50 = 63 and 115 nM, compared to 33 nM for finasteride) and P450(17 alpha) (IC50 = 43 and 25 nM, compared to 78 nM for ketoconazole). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Steroidal Sapogenins. No. 167. Pregnene Derivatives from Nologenin
  作者：Russell E. Marker

  DOI：10.1021/ja01202a043

  日期：1947.10
• Synthesis of new formyl and aminomethyl steroids via homogeneous catalysis
  作者：Szilárd Törös、Ilona Gémes-Pécsi、Bálint Heil、Sándor Mahó、Zoltán Tuba

  DOI：10.1039/c39920000858

  日期：——

  New formyl-pregnene, formyl-androstene and the corresponding aminomethyl derivatives are synthesised selectively via hydroformylation with a rhodium-phosphine catalyst prepared in situ.