2α-bromodihydrotestosterone | 29041-91-6

• 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: 2α-bromodihydrotestosterone
• 英文别名: 2α-bromo-17β-hydroxy-5α-androstan-3-one；2α-Brom-17β-hydroxy-5α-androstan-3-on；Androstan-3-one, 2-bromo-17-hydroxy-, (2alpha,5alpha,17beta)-；(2R,5S,8R,9S,10S,13S,14S,17S)-2-bromo-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 29041-91-6
• 化学式: C₁₉H₂₉BrO₂
• 分子量: 369.342
• InChiKey: JJLHVQHZLWNYFI-TVGHHNFTSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  448.6±45.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  2α-bromodihydrotestosterone 在 chromium(VI) oxide 、 硫酸 作用下， 以 乙醚 、 丙酮 、 苯 为溶剂， 生成 (5α,17β)-17-甲基-2-雄烯-3,17-二醇
  参考文献：
  名称：

  STEROIDS。CCV。响一个修改过的激素模拟。I.敲响烯烃。

  摘要：

  DOI：

  10.1021/jm00338a016
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢溴酸 、 溴 、 溶剂黄146 作用下， 生成 2α-bromodihydrotestosterone
  参考文献：
  名称：

  Butenandt; Dannenberg, Chemische Berichte, 1936, vol. 69, p. 1158,1161

  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。
• Synthesis and investigation of certain androstane derivatives of 5-fluorouracil
  作者：L. N. Volovel'skii、I. A. Rastrepina、N. V. Popova、V. N. Koryukina、A. A. Zidermane、A. Zh. Dauvarte

  DOI：10.1007/bf01148631

  日期：1986.9

  tumors [i]. Because of its high toxicity, it is presently employed in its N-substituted forms, e.g., l-(2-furanidyl)-5-fluorouracil (fluorofur) [4J. Based on the assumption that dihydrotestosterone derivatives which easily penetrate cell membranes would be good conductors of this antimetabolite, we synthesized N-derivatives of 5-fluorouracil, dihydrotestosterone, and 17=-methyl dihydrotestosterone according

  核酸拮抗剂5-氟尿嘧啶已广泛用于治疗多种恶性肿瘤[i]。由于其高毒性，它目前以其 N-取代形式使用，例如，1-(2-呋喃基)-5-氟尿嘧啶 (fluorofur) [4J. 基于容易穿透细胞膜的二氢睾酮衍生物是这种抗代谢物的良导体的假设，我们根据以下模式合成了 5-氟尿嘧啶、二氢睾酮和 17=-甲基二氢睾酮的 N-衍生物：
• Controlled alkaline hydrolysis of steroidal α-bromoketones: New conditions and synthesis of 2α-hydroxy-3-ones
  作者：Mitsuteru Numazawa、Masao Nagaoka

  DOI：10.1016/0039-128x(82)90152-0

  日期：1982.3

  Controlled alkaline hydrolysis of 16 alpha-bromo-17-keto steroids 1, 5 and 7 with potassium carbonate and tetra-n-butylammonium hydroxide (n-Bu4NOH) and synthesis of 2 alpha-hydroxy-3-ones 11, 13 and 16 by the controlled hydrolysis of the corresponding 2 alpha-bromo-3-ones 9, 12 and 15 are described. Treatment of the bromoketones 1,5 and 7 with potassium carbonate in aqueous acetone or with n-Bu4NOH

  用碳酸钾和四正丁基氢氧化铵（n-Bu4NOH）控制16种α-溴17-酮类固醇1、5和7的碱水解，并通过以下方法合成2α-羟基-3-酮11、13和16描述了相应的2个α-溴-3-酮9、12和15的受控水解。在丙酮水溶液中用碳酸钾或在二甲基甲酰胺水溶液（DMF）中用n-Bu4NOH处理溴酮1,5和7，分别以85-90％的产率得到16个α-羟基-17-酮3m 6和8。通过分别使用上述条件或氢氧化钠在吡啶或DMF中的高产率水解相应的溴代酮9、12和15，得到2个α-羟基-3-酮11、13和16。
• Synthesis of Symmetrical Bis-Steroid Pyrazines Connected via D-Rings
  作者：Ivan Černý、Vladimír Pouzar、Miloš Buděšínský、Pavel Drašar

  DOI：10.1135/cccc20001597

  日期：——

  Bis-steroid pyrazines fused through rings D of the steroid skeleton were synthesized. Methods for the preparation of the corresponding rings A fused derivatives (cephalostatin type) were checked on simple androstanes and then a symmetrical D fused analogue, 5α-androstano[16'',17''-5',6']pyrazino[2',3'-16,17]-5α-androstane-3β,3''b-diol, was prepared. Partially substituted bis-steroid pyrazines in both series were prepared and their use for the preparation of higher fused compounds was discussed. No significant cytostatic activity was found on parent bis-steroid pyrazines both A and D fused.

  合成了通过类固醇骨架上的环D融合的双甾体吡嗪。在简单的类雄甾烷上检查了相应的环A融合衍生物（头孢菌素类）的制备方法，然后制备了一个对称的D融合类似物，5α-雄甾烷[16'',17''-5',6']吡嗪[2',3'-16,17]-5α-雄甾烷-3β,3''b-二醇。在两个系列中制备了部分取代的双甾体吡嗪，并讨论了它们用于制备更高级别的融合化合物的使用。在父体双甾体吡嗪（A和D融合）上未发现显着的细胞毒活性。
• New stereoselective synthesis of 5α-androst-1-ene-3β,17β-diol
  作者：E. I. Chernoburova、M. A. Shchetinina、V. A. Korolev、A. I. Ilovaisky、I. V. Zavarzin

  DOI：10.1007/s11172-023-4078-5

  日期：2023.11

  Efficient stereoselective methods for the synthesis of 5α-androst-1-ene-3β,17β-diol, which is used as a reference compound for identification of anabolic steroids and their metabolites, were elaborated. The key factor of the synthesis is the use of the sodium borohydride—cerium(III) chloride system as a reducing agent.

  详细阐述了合成代谢类固醇及其代谢物的参考化合物5α-androst-1-ene-3β,17β-二醇的高效立体选择性合成方法。合成的关键在于使用硼氢化钠-氯化铈(III)体系作为还原剂。