(3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione | 157302-54-0

• 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: (3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione
• 英文别名: 3-[(1,1-dimethylethyl)dimethylsilyl]oxy-5-androstene-7,17-dione；3β-(t-butyldimethylsilyloxy)androst-5-ene-7,17-dione；3β-tert-butyldimethylsilyloxyandrost-5-en-7,17-dione；(3S,8R,9S,10R,13S,14S)-3-[tert-butyl(dimethyl)silyl]oxy-10,13-dimethyl-2,3,4,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-7,17-dione
• CAS: 157302-54-0
• 化学式: C₂₅H₄₀O₃Si
• 分子量: 416.676
• InChiKey: QMVDWGVFZDCTIG-DBHQNMABSA-N

物化性质

• 熔点：
  127-129 °C
• 沸点：
  490.0±45.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二氯甲烷、四氢呋喃

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione 在 盐酸 、 sodium tetrahydroborate 、 cerium(III) chloride 、 水 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 生成 HE-3177
  参考文献：
  名称：

  Novel components of the human metabolome: The identification, characterization and anti-inflammatory activity of two 5-androstene tetrols

  摘要：

  Two natural 5-androstene steroid tetrols, androst-5-ene-3 beta,7 beta,16 alpha,17 beta-tetrol (HE3177) and androst-5-ene-3 alpha,7 beta,16 alpha,17 beta-tetrol (HE3413), were discovered in human plasma and urine. These compounds had significant aqueous solubility, did not bind or transactivate steroid-binding nuclear hormone receptors. and were not immunosuppressive in murine mixed-lymphocyte studies. Both compounds appear to be metabolic end products, as they were resistant to primary and secondary metabolism. Both were orally bioavailable, and were very well tolerated in a two-week dose-intensive toxicity study in mice. Anti-inflammatory properties were found with exogenous administration of these compounds in rodent disease models of multiple sclerosis, lung injury, chronic prostatitis, and colitis. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.10.005
• 作为产物：
  描述：

  (3S)-3-tert-butyldimethylsilyloxyandrost-5-en-17-one 在 dirhodium tetrakis[μ-(hexahydro-2H-azepin-2-onato-κN1:κO2)]acetonitrile 、 叔丁基过氧化氢 作用下， 以 1,2-二氯乙烷 、 水 为溶剂， 反应 24.08h， 以66%的产率得到(3β)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5-ene-7,17-dione
  参考文献：
  名称：

  Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[ε-caprolactamate] of tert-Butyldimethylsilyl-protected trans-Dehydroandrosterone

  摘要：

  DOI：

  10.15227/orgsyn.089.0019

文献信息

• Mild Manganese(III) Acetate Catalyzed Allylic Oxidation:  Application to Simple and Complex Alkenes
  作者：Tony K. M. Shing、Yeung、Pak L. Su

  DOI：10.1021/ol0612298

  日期：2006.7.1

  Manganese(III) acetate catalyzed allylic oxidation of alkenes to the corresponding enones was investigated, showing excellent regioselectivity and chemoselectivity (functional group compatibility). Delta(5)-Steroids were transformed into bioactive Delta(5)-en-7-ones under a nitrogen atmosphere, whereas simple alkenes were converted into the corresponding enones under an oxygen atmosphere in good yields.
• Back, Thomas G.; Baron, Denise L.; Morzycki, Jacek W., Heterocycles, 1994, vol. 38, # 5, p. 1053 - 1060
  作者：Back, Thomas G.、Baron, Denise L.、Morzycki, Jacek W.

  DOI：——

  日期：——
• Ergosteroids IV: synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates
  作者：Padma Marwah、Ashok Marwah、Nancy Kneer、Henry Lardy

  DOI：10.1016/s0039-128x(00)00234-8

  日期：2001.7

  The 7-oxo derivative of dehydroepiandrosterone is more active than the parent steroid and is devoid of adverse side effects in rats, monkeys and humans. In anticipation of possible therapeutic use we have sought more active, longer lasting forms of 7-oxo- and 7 beta -hydroxydehydroepiandrosterones. The 7-oxo- and 7-hydroxy steroids have been converted to glucuronides, ethers and carbonate esters. The syntheses of these compounds are described and their ability to induce the formation of liver thermogenic enzymes when fed to rats is reported. Some of the new derivatives were found to be somewhat more effective than the equimolar amounts of 7-oxo-DHEA with which they were compared in each experiment. (C) 2001 Elsevier Science Inc. All rights reserved.
• Novel components of the human metabolome: The identification, characterization and anti-inflammatory activity of two 5-androstene tetrols
  作者：Clarence N. Ahlem、Theodore M. Page、Dominick L. Auci、Michael R. Kennedy、Katia Mangano、Ferdinando Nicoletti、Yu Ge、Yujin Huang、Steven K. White、Sonia Villegas、Douglas Conrad、Angela Wang、Christopher L. Reading、James M. Frincke

  DOI：10.1016/j.steroids.2010.10.005

  日期：2011.1

  Two natural 5-androstene steroid tetrols, androst-5-ene-3 beta,7 beta,16 alpha,17 beta-tetrol (HE3177) and androst-5-ene-3 alpha,7 beta,16 alpha,17 beta-tetrol (HE3413), were discovered in human plasma and urine. These compounds had significant aqueous solubility, did not bind or transactivate steroid-binding nuclear hormone receptors. and were not immunosuppressive in murine mixed-lymphocyte studies. Both compounds appear to be metabolic end products, as they were resistant to primary and secondary metabolism. Both were orally bioavailable, and were very well tolerated in a two-week dose-intensive toxicity study in mice. Anti-inflammatory properties were found with exogenous administration of these compounds in rodent disease models of multiple sclerosis, lung injury, chronic prostatitis, and colitis. (C) 2010 Elsevier Inc. All rights reserved.
• Allylic Oxidation Catalyzed by Dirhodium(II) Tetrakis[ε-caprolactamate] of tert-Butyldimethylsilyl-protected trans-Dehydroandrosterone
  作者：Ratnikov, Maxim O.、Goldmann, Petra L.、McLaughlin, Emily、Doyle, Michael P.

  DOI：10.15227/orgsyn.089.0019

  日期：——