d₂-dehydroepiandrosterone | 67034-83-7

• 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: d₂-dehydroepiandrosterone
• 英文别名: Dehydroepiandrosterone-16,16-D2；(3S,8R,9S,10R,13S,14S)-16,16-dideuterio-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthren-17-one
• CAS: 67034-83-7
• 化学式: C₁₉H₂₈O₂
• 分子量: 290.414
• InChiKey: FMGSKLZLMKYGDP-MWTYYLDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 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：

  d₂-dehydroepiandrosterone 在 bis-triphenylphosphine-palladium(II) chloride 、 碘 、 sodium carbonate 、 一水合肼 、 四甲基胍 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 为溶剂， 反应 5.0h， 生成 (3β)-17-(3-pyridyl)androst-5,16-dienol-16-d
  参考文献：
  名称：

  EP3392261

  摘要：

  公开号：
• 作为产物：
  描述：

  去氢表雄酮 在 重水 、 硼酸 作用下， 反应 6.0h， 以54%的产率得到d₂-dehydroepiandrosterone
  参考文献：
  名称：

  离子液体/硼酸系统可使用 D2O 进行氘化

  摘要：

  开发用于多位点氘化的无过渡金属系统对于氘标记药物和中间体的制备具有重要意义。我们报道了离子液体[bmim]PF 6能够促进硼酸与D 2 O 的高效氘去硼酸化反应。离子液体/硼酸体系成功地应用于不同sp 2 /sp 3 C条件下的选择性H/D 交换。 H 职位。此外，观察到离子液体中含氮杂芳烃的异常亲核行为。

  DOI：

  10.1016/j.tetlet.2022.153968

文献信息

• 一种在离子液体介质中合成氘代化合物的方法
  申请人：句容宁武新材料股份有限公司

  公开号：CN114933516A

  公开（公告）日：2022-08-23

  本发明公开了一种在离子液体介质中合成氘代化合物的方法，包括以下步骤：以氘水为氘源，在离子液体溶剂中，化合物与硼酸在空气下加热反应，得到相应位点氢氘交换的化合物。本发明以相对廉价易得的氘水为氘源，以[bmim]PF6离子液体为溶剂，在硼酸为添加剂的条件下，一步实现化合物的氢氘交换。该方法具有条件温和、原子经济性高、环保等优势，有很好的理论价值及应用前景。
• Disturbance in sex-steroid serum profiles of cattle in response to exogenous estradiol: A screening approach to detect forbidden treatments
  作者：Patricia Regal、Carolina Nebot、Mónica Díaz-Bao、Rocio Barreiro、Alberto Cepeda、Cristina Fente

  DOI：10.1016/j.steroids.2010.12.005

  日期：2011.3

  Estradiol benzoate (EB) has been one of the most widely used estrogenic agents in animal husbandry, as a way of exogenously introducing the natural hormone estradiol-17 beta into the animal organism. Estradiol was previously employed to induce anabolic effects or reproductive improvements in cattle. However, the employment of EB in European countries has been permanently forbidden by Directive 2008/97/EC to guarantee consumers' health. Despite this prohibition, the control of estradiol-17 beta and its esters continues to be a difficult task for residue-monitoring plans in European Communities because official analyses of natural thresholds for hormones in cattle have not yet been established, leading to a lack of confirmation for any exogenous administration of natural hormones. Several researchers have worked on excretion profiles of metabolites, variation in specific hormonal ratios and metabolomic fingerprints after hormonal treatments. This research focuses on the possible existence of disturbances in the serum profile of animals treated with EB in terms of steroid sex hormones (androgens, oestrogens and progestogens), by investigating the serum levels of several of these hormones. The serum samples were collected from three groups of cows: one treated with an intramuscular injection of EB, one treated with a combination of intravaginal EB and progesterone and a control (non-treated) group. The samples have been analysed by a validated high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) method, and 17 natural hormones were identified and quantified. Subsequently, data from the serum profiles were submitted for statistic and multivariate analysis, and it was possible to observe a manifest variation between animal groups. The obtained results can help in the development of a viable screening tool for monitoring purposes in cattle. (C) 2010 Elsevier Inc. All rights reserved.
• Application of gas chromatography/mass spectrometry to steroid analysis in equine sports: Problems with enzyme hydrolysis
  作者：E. Houghton、L. Grainger、M. C. Dumasia、P. Teale

  DOI：10.1002/oms.1210271016

  日期：1992.10

  AbstractIn steroid analysis in biological fluids, cleavage of conjugates is an essential step which can be achieved by either enzymatic or chemical hydrolysis. Where conjugation with both glucuronic acid and sulphate occurs, then the use of the enzyme preparation from Helix pomatia, containing both β‐glucuronidase and aryl sulphatase activities, would appear to be advantageous. However, it has been shown that the sulphatase enzymes of Helix pomatia do not hydrolyse 17β‐sulphates and that other enzymatic activities also present in the preparation can give rise to artefact formation with certain steroids.The artefacts produced from incubation of dehydroisoandrosterone with the enzyme preparation from Helix pomatia have been identified by gas chromatography/mass spectrometry (GC/MS) as androst‐4‐ene‐3,17‐dione, androsta‐4,6‐diene‐3,17‐dioue, androst‐4‐ene‐3,6,17‐trione and 6‐hydroxyandrost‐4‐ene‐3,17‐dione. Incubation of androst‐5‐ene‐3,17‐diol produced a similar series of compounds with a 17‐hydroxy function. Semi‐quantitative GC/MS analysis has been used to determine the extent of these transformations in the presence of increasing amounts of the Helix pomatia preparation. Quantitative conversion in buffer can be obtained but the results from incubation in urine showed a marked modifying effect with minimal artefact formation. The enzyme preparation from Escherichia coli does not yield any artefacts and results are presented for the optimization of its use in the hydrolysis of the glucuronic acid conjugate of 5α‐estrane‐3β,17α‐diol, the major metabolite of nandrolone in the horse.