3β-hydroxy-D-homo-5-androstene-17a-one | 3278-99-7

• 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
• 英文名称: 3β-hydroxy-D-homo-5-androstene-17a-one
• 英文别名: (4aS,4bR,8S,10aR,10bS,12aS)-8-hydroxy-10a,12a-dimethyl-3,4,4a,4b,5,7,8,9,10,10b,11,12-dodecahydro-2H-chrysen-1-one
• CAS: 3278-99-7
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: DIYCXBQZJHJHQI-BGZMIMFDSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  441.0±45.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  22.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3β-hydroxy-D-homo-5-androstene-17a-one 在 氢氧化钾 、 一水合肼 作用下， 以 二乙二醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Syntheses and ultraviolet absorption of aza-steroids

  摘要：

  A series of aza-steroids was synthesized containing chromophoric groups, such as a, beta-unsaturated ketones and doubly unsaturated conjugated and monoconjugated heteroannular dienones with the heteroatom in the D ring at the 20 and 17a positions. The effect of an appositely placed electronegative center in these molecules upon their ultraviolet absorptions was studied. In order to obtain a basis for the observed spectral changes, the corresponding carbocyclic compounds were also synthesized. The maximum absorptions of the aza-steroids were hypsochromically shifted relative to the carbocyclic compounds in all cases (n=8). The displacement caused by the electronegative center on absorption maximum of the chromophores is, however, highly dependent on its location within the molecules.

  DOI：

  10.1016/0039-128x(76)90099-4
• 作为产物：
  描述：

  2',2'-dimethyl-(17βO)-spiro[androst-5-ene-17,5'-oxazolidin]-3β-ol 在 溶剂黄146 、 sodium nitrite 作用下， 生成 3β-hydroxy-D-homo-5-androstene-17a-one
  参考文献：
  名称：

  Quinkert,G. et al., Chemische Berichte, 1965, vol. 98, p. 2742 - 2753

  摘要：

  DOI：

文献信息

• Azasteroids: structure-activity relationships for inhibition of 5.alpha.-reductase and of androgen receptor binding
  作者：Gary H. Rasmusson、Glenn F. Reynolds、Nathan G. Steinberg、Edward Walton、Gool F. Patel、Tehming Liang、Margaret A. Cascieri、Anne H. Cheung、Jerry R. Brooks、Charles Berman

  DOI：10.1021/jm00161a028

  日期：1986.11

  In addition, 4-azasteroids with a D-homo ring or methyl substitution at C-7 (alpha and beta) or C-16 (alpha and beta) were prepared. The majority of the C-17 substituents were prepared from reactive intermediates derived from the 17 beta-COOH. Enhanced 5 alpha-reductase inhibition in both the human and rat enzyme assays is seen with 4-CN substitution on 3-oxo-delta 4 steroids and with a C-17 side

  制备了一系列类固醇，主要是4-氮杂类固醇，并在体外进行了测试，以作为人和大鼠前列腺5α-还原酶以及二氢睾丸激素与大鼠雄激素受体结合的抑制剂。主要的结构修饰是类固醇核的C-17位置的A环和连接部分的变化。新的A环修改包括碳环系列中的4-cyano-3-oxo-delta 4系统和1 alpha-CN，1 alpha-CH3、1 alpha，2 alpha-CH2、2 beta-F，2-aza， 3-oxo-4-aza系列中的2-oxa和A-homo变化。另外，制备了在C-7（α和β）或C-16（α和β）具有D-高环或甲基取代的4-氮杂甾类。大多数C-17取代基是由衍生自17β-COOH的反应性中间体制备的。在人和大鼠酶试验中，通过在3-oxo-delta 4类固醇上进行4-CN取代和在4-aza-3上结合了亲脂性取代的半极性基团的C-17侧链，可以看到增强的5α-还原酶抑制作用-oxo-5α
• Über Steroide und Sexualhormone. 169. Mitteilung. D-Homo-dehydro-epi-androsteron und eine neue Synthese des D-Homo-testosterons
  作者：H. Heusser、P. Th. Herzig、A. Fürst、Pl. A. Plattner

  DOI：10.1002/hlca.19500330440

  日期：——

  überführen lässt. Ausgehend von diesem bis jetzt nicht beschriebenen Keton konnten nach den in der normalen Steroid-Reihe verwendeten Methoden eine-Anzahl Derivate der Ring-Homologen des Testosterons und der Androstendiole leicht erhalten werden.

  用氢化锂铝将脱氢表雄甾酮乙酸酯的氰醇二乙酸酯XIIIa还原为氢化胺XVI，具有优异的收率，可通过脱氨基容易地转化为D-均-脱氢-表雄酮（XX）。从迄今未描述的酮开始，可以通过常规甾族化合物中使用的方法容易地获得睾丸激素和雄烯二醇的环同系物的许多衍生物。
• D-homoandrostanes.4. The incubation of some D-homo-5α-androstanes with Rhizopus nigricans
  作者：Deanna de Marcano、JoséF. del Giorgio、John M. Evans、Eleida Garcia、Ladislav Kohout、Ivonne Ludovic、María Narvaez

  DOI：10.1016/0039-128x(83)90011-9

  日期：1983.1

  Nine dioxygenated D-homoandrostanes were incubated with Rhizopus nigricans to investigate the effect of D-ring modification on microbiological hydroxylation. Structure determination of the products by NMR spectroscopy, and in certain cases independent synthesis of their oxidised products, showed that in contrast to 5 alpha-androstanes the majority of the compounds were hydroxylated in the "reverse"

  将九种双加氧的D-高雄甾烷与黑根霉菌一起孵育，以研究D环修饰对微生物羟基化的影响。通过NMR光谱确定产物的结构，并在某些情况下对其氧化产物进行独立合成，结果表明，与5α-雄烷相反，大多数化合物以“反向”模式被羟基化，只有D-homo-5 α-雄烷-3,17-二酮在“正常”模式下有任何程度的羟基化。D-homo-5 alpha-雄甾烷-3,6-和3,7-二酮均在C（17 alpha）处观察到立体特异性环D-羟基化。
• An efficient procedure for the regiospecific preparation of d-homo-steroid derivatives
  作者：Roberte Pellicciari、Benedetto Natalini、Renata Fringuelli

  DOI：10.1016/0039-128x(87)90016-x

  日期：1987.4

  alpha-Diazo-beta-hydroxy esters 3, obtained by condensation of ketones 1 with ethyl diazo(lithio)acetate 2, are efficiently converted into the corresponding beta-ketoesters 4 by exposure to dirhodium (II) tetraacetate. Application of this two-step sequence to 3 beta-acetoxy-5-androstene-17-one 5b and to 3-acetoxy estrone 10b afforded regiospecifically and in very high overall yield the corresponding ethyl 17a-oxo-D-homo-steroid-17-carboxylates 7a,b and 12a,b, which were decarboalkoxylated to give, respectively, 3 beta-hydroxy-D-homo-5-androstene-17a-one 8 and D-homoestrone 13.
• SCHUBERT; STACHOWIAK; ONKEN, Pharmazie, 1963, vol. 18, p. 323 - 331
  作者：SCHUBERT、STACHOWIAK、ONKEN、SPECHT、BARNIKOL-OETTLER、BODE、HELLER、POHNERT、SCHWARZ、ZEPTER

  DOI：——

  日期：——