3-oximino-androst-4-en-17β-ol | 6911-95-1

• 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: 3-oximino-androst-4-en-17β-ol
• 英文别名: 17β-hydroxy-androst-4-en-3-one oxime；17β-Hydroxy-androst-4-en-3-on-oxim；oxime of testosterone；Testosteron-oxim；Androst-4-en-3-one, 17-hydroxy-, oxime, (17beta)-；(8R,9S,10R,13S,14S,17S)-3-hydroxyimino-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-ol
• CAS: 6911-95-1
• 化学式: C₁₉H₂₉NO₂
• 分子量: 303.445
• InChiKey: CCDNGLFWWXCDAW-DYKIIFRCSA-N

物化性质

• 沸点：
  467.0±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 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：
  52.8
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-oximino-androst-4-en-17β-ol 在 吡啶 、 sodium 作用下， 以 正丁醇 为溶剂， 反应 2.0h， 生成 diacetyl derivative of 3b
  参考文献：
  名称：

  Nucleosteroids: carbocyclic nucleoside analogs of androst-4-en-17β-ol

  摘要：

  Steroidal nucleoside analogs were synthesized starting from testosterone. By reduction of the oxime of 17beta-hydroxy-androst-4-en-3-one (testosterone), a mixture of the two amino epimers of C-3 were obtained. The 3alpha-amino-androst-4-en-17beta-ol was crystallized in 73% yield and coupled with 5-amino-4,6-dichloropyrimidine to give 3alpha-(5'-amino-4'-chloro-pyrimidin-6'-yl)amino-androst-4-en-17beta-ol. This compound was treated with triethyl orthoformate in acid media to give the corresponding purinyl steroid adduct 3alpha-(6'-chloro-purin-9'-yl)-androst-4-en- 17beta-ol in 98% yield. This substance, in turn, was converted with good yield into the 6'-thio, 6'-methylamino, and 6'-diethyl aminopurinyl derivatives through nucleophilic reactions at C-6 of the purine nucleus. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(01)00157-x
• 作为产物：
  描述：

  (3b,17b)-雄甾-5-烯-3,17-二醇 3,17-二乙酸酯 在 甲醇 、 氢氧化钾 、 溴 、 溶剂黄146 作用下， 生成 3-oximino-androst-4-en-17β-ol
  参考文献：
  名称：

  Butenandt; Hanisch, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1935, vol. 237, p. 89,95

  摘要：

  DOI：

文献信息

• Contragestational agents. 1. Steroidal-O-aryloximes
  作者：Allen F. Hirsch、George O. Allen、Benny Wong、Sandra Reynolds、Chris Exarhos、William Brown、Do Won Hahn

  DOI：10.1021/jm00222a002

  日期：1977.12

  The preparation of a series of O-aryloximes of various steroids by two different routes is described. These compounds were prepared by reacting a keto steroid with a substituted O-arylhydroxylamine in the presence of an acid catalyst or, alternatively, by the reaction of a steroidal oxime with a substituted aryl halide in the presence of a suitable base. These compounds were examined for their ability

  描述了通过两种不同的途径制备一系列各种类固醇的O-芳基肟。这些化合物是通过在酸催化剂的存在下使酮类固醇与取代的O-芳基羟胺反应或通过在合适的碱存在下使类固醇肟与取代的芳基卤反应来制备的。检查了这些化合物在雌性大鼠中中断植入后妊娠的能力。化合物的甾体基本结构为5α-雄甾烷，3-肟为对硝基苯基系列，具有最显着的避孕活性。当在妊娠第9-12天以2.5 mg / kg的剂量口服给予大鼠时，该系列中最活跃的化合物之一（16）被证明具有终止妊娠的能力。
• Prolonged release of antifertility drugs
  申请人：IIT Research Institute

  公开号：US03968105A1

  公开（公告）日：1976-07-06

  Antifertility drug complexes which have enhanced effectiveness and prolonged release of the antifertility drug. The complex includes an antifertility drug, a polybasic acid and a polyvalent metal ion. The antifertility drug is in the form of a basic amine derivative.

  抗生育药物复合物具有增强效果和延长释放抗生育药物的特性。该复合物包括抗生育药物、多元酸和多价金属离子。抗生育药物以碱性胺衍生物的形式存在。
• Convenient preparation of A-ring fused pyridines from steroidal enamides
  作者：Madan G. Barthakur、Moyurima Borthakur、Romesh C. Boruah

  DOI：10.1016/j.steroids.2008.04.016

  日期：2008.10

  A facile strategy for the preparation of A-ring fused pyridosteroids has been accomplished in high yields by the reaction of Vilsmeier reagent (chloromethyleneiminium salt) with steroidal A-ring enamides (2- and 3-ene) under thermal conditions. The structure of 6'-chloro-5 alpha-cholest [3,2-b]pyridine was determined by X-ray analysis. (c) 2008 Elsevier Inc. All rights reserved.
• 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.
• Sexualhormone VII. Über die künstliche Herstellung des Testikelhormons Testosteron (Androsten-3-on-17-ol)
  作者：L. Ruzicka、A. Wettstein

  DOI：10.1002/hlca.193501801176

  日期：——