9-去氢睾酮 | 2398-99-4

• 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
• 中文名称: 9-去氢睾酮
• 英文名称: 17β-Hydroxy-androsta-4,9(11)-dien-3-on
• 英文别名: Δ⁹⁽¹¹⁾-testosterone；9-Dehydrotestosterone；(8S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 2398-99-4
• 化学式: C₁₉H₂₆O₂
• 分子量: 286.414
• InChiKey: IUFOPOQNYKRRML-FQQAFBJJSA-N

物化性质

• 熔点：
  153-154 °C
• 沸点：
  448.1±45.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、甲醇（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9-去氢睾酮 在 4-硝基过氧化苯甲酸 、 氢氟酸 、 三氟化硼 作用下， 以 二氯甲烷 为溶剂， 反应 28.0h， 生成 hydroxy-17β androstatriene-4,8,14 one-3
  参考文献：
  名称：

  Audouin, Max; Levisalles, Jacques, Bulletin de la Societe Chimique de France, 1985, # 6, p. 1280 - 1284

  摘要：

  DOI：
• 作为产物：
  描述：

  氢化可的松 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 对甲苯磺酸 、 溶剂黄146 、 原甲酸三乙酯 作用下， 以 吡啶 、 甲醇 、 苯 为溶剂， 反应 8.0h， 生成 9-去氢睾酮
  参考文献：
  名称：

  Synthesis of 11-substituted androstenediones and testosterones as human decidual cell growth inhibitors

  摘要：

  11 alpha-Hydroxytestosterone (1a), 11 beta-hydroxytestosterone (1b), 11 alpha-methoxytestosterone (1c), 11 beta-methoxytestosterone (1d), 11-ketotestosterone (1e), and Delta(9(11))-testosterone (1f) were synthesized from hydrocortisone (4b) or 11-epi-hydrocortisone (4a). The six target compounds, together with 11 alpha-methoxyandrostenedione (2c), 11 beta-methoxyandrostenedione, (2d) and their lead compound, testosterone (1), were found to effectively inhibit the growth and differentiation of human decidual cells in culture. There is no observable binding of these compounds to estrogen receptor of rabbit uterus. The introduction of apolar group (e.g., hydroxyl and carbonyl) to C-11 of androstenes decreases both the relative binding affinities to progesterone receptor and the inhibitory effects on human decidual cell growth, while the methylation of 11-hydroxyl group minimizes these effects. The similar effects of a polar group at C-11 of testosterone (1) on the inhibitory effects on human decidual cell growth and the relative binding affinities to progesterone receptor of rabbit uterus may suggest that one of the mechanisms of human decidual cell growth inhibition by these compounds is the anti-progestational activity of these androgens.

  DOI：

  10.1016/0039-128x(94)90027-2

文献信息

• Regio- and stereoselective reduction of 17-oxosteroids to 17β-hydroxysteroids by a yeast strain Zygowilliopsis sp. WY7905
  作者：Yuanyuan Liu、Yu Wang、Xi Chen、Qiaqing Wu、Min Wang、Dunming Zhu、Yanhe Ma

  DOI：10.1016/j.steroids.2016.11.002

  日期：2017.2

  The reduction of 17-oxosteroids to 17beta-hydroxysteroids is one of the important transformations for the preparation of many steroidal drugs and intermediates. The strain Zygowilliopsis sp. WY7905 was found to catalyze the reduction of C-17 carbonyl group of androst-4-ene-3,17-dione (AD) to give testosterone (TS) as the sole product by the constitutive 17beta-hydroxysteroid dehydrogenase (17beta-HSD)

  17-氧甾体向17β-羟基甾体的还原是制备许多甾体药物和中间体的重要转变之一。菌株Zygowilliopsis sp。发现WY7905通过组成型17β-羟基类固醇脱氢酶（17beta-HSD）催化雄酮-4-烯-3,17-二酮（AD）的C-17羰基还原，从而产生睾丸激素（TS）作为唯一产物。 。还原的最佳条件是pH 8.0和30摄氏度，补充10g / l葡萄糖和1％Tween 80（w / v）。在优化的转化条件下，将0.75g / l的AD还原为单一产物TS，其在24小时内的收率> 90％，非对映异构体过量（de）超过99％。该菌株还还原了其他17种氧类固醇，例如雌酮，3beta-hydroxyandrost-5-en-17-one和norandrostenedione，得到相应的17β-羟基类固醇，而C-3和C-20羰基完好无损。在这种微生物17β还原中不存在副产物将有助于产物纯化。这样
• Hydroxyl groups at C-3 and at C-17 of the unnatural enantiomer, ent-androsta-5,9(11)-diene-3β,17β-diol are oxidised by cholesterol oxidase from Rhodococcus erythropolis
  作者：Dai Kitamoto、Serge Dieth、Alain Burger、Denis Tritsch、Jean-François Biellmann

  DOI：10.1016/s0040-4039(00)02005-0

  日期：2001.1

  The ent-androsta-4,9(11)-diene-3β,17β-diol 1b and ent-androsta-5,9(11)-diene-3β,17β-diol 2b prepared from chiral dione 3, were oxidised by cholesterol oxidase with kinetic parameters close to those of the natural steroids 1a and 2a. In the preparative oxidation the final product was ent-androsta-4,9(11)-diene-3,17-dione 5. So the enzyme catalysed the oxidation of the hydroxyl groups at C-3 and C-17

  由手性二酮3制备的ent -androsta-4,9（11）-diene-3β，17β-二醇1b和ent -androsta-5,9（11）-diene-3β，17β-二醇2b被胆固醇氧化氧化酶的动力学参数接近天然类固醇1a和2a。在制备氧化的最终产物是ENT -雄-4,9（11） -二烯-3,17-二酮5。因此，该酶催化C-3和C-17处羟基的氧化，而天然对映异构体仅在C-3处被氧化。
• 9(11)-Dehydrotestosterone and Esters
  作者：F. W. Heyl、M. E. Herr

  DOI：10.1021/ja01607a084

  日期：1955.1
• Nedelec,L.; Gasc,J.C., Bulletin de la Societe Chimique de France, 1970, p. 2556 - 2564
  作者：Nedelec,L.、Gasc,J.C.

  DOI：——

  日期：——
• C(10)-Methylation of Steroidal Synthesis Intermediate BCD-Tricyclic 9-En-5-ones
  作者：John W. Scott、Paul Buchschacher、Ludwik Labler、Werner Meier、Andor Fürst

  DOI：10.1002/hlca.19740570433

  日期：1974.4.27

  AbstractA literature survey indicated that stereospecific non‐reductive β‐face methylation at C(10) of steroidal synthesis intermediate BCD‐tricyclic 9‐en‐5‐ones had never been effected. An attempt to define the factors controlling the β/α product ratio in such alkylations was made. The course of methylation is significantly affected by the temperature. In the best case, methylation of the sodium enolate of 17 β‐t‐butoxy‐19‐(3,5‐dimethyl‐4‐isoxazolyl)‐deA‐androst‐9‐en‐5‐one (18) in tetrahydrofuran at − 78° gave a β/α product ratio of > 5:1. The reaction mixture contained no unalkylated or dialkylated materials, indicating that enolate exchange probably did not occur at this temperature. The 10β‐methylated product 23, isolated in 78% yield, was converted to Δ9(ll)‐dehydrotestosterone (29). Compounds 23 and 29 are potential intermediates for the synthesis of 11‐oxygenated steroids.