6β-fluoro-17β-hydroxy-4-androsten-3-one | 1852-58-0

• 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: 6β-fluoro-17β-hydroxy-4-androsten-3-one
• 英文别名: 6β-fluoro-4-androsten-17β-ol-3-one；6β-fluoro-17β-hydroxy-androst-4-en-3-one；6β-Fluor-17β-hydroxy-androst-4-en-3-on；(6β,17β)-6-fluoro-17-hydroxy-androst-4-en-3-one；6|A-fluoro-17|A-hydroxyandrost-4-en-3-one；(6R,8R,9S,10R,13S,14S,17S)-6-fluoro-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
• CAS: 1852-58-0
• 化学式: C₁₉H₂₇FO₂
• 分子量: 306.421
• InChiKey: GGQPTOITOZXLBE-ZVBLRVHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6β-fluoro-17β-hydroxy-4-androsten-3-one 在 盐酸 、 溶剂黄146 作用下， 生成 (6alpha,17beta)-6-氟-17-羟基雄甾-4-烯-3-酮
  参考文献：
  名称：

  卤代类固醇激素的合成—Ⅱ

  摘要：

  用三氟化硼醚化物在胆甾烷，雄烷酮和孕烷系列中裂解3β-乙酰氧基-5α-，6α-环氧化合物，得到相应的3β-乙酰氧基-5α-羟基-6β-氟代化合物。通过适当地操作这些氟代醇，可制得6α-氟胆甾烯酮和具有生物学意义的6α-和6β-氟睾酮以及6α-6β-氟孕酮。

  DOI：

  10.1016/s0040-4020(01)82606-5
• 作为产物：
  描述：

  3β,17β-diacetoxy-6β-fluoro-androst-4-ene 在 manganese(IV) oxide 、 lithium aluminium tetrahydride 作用下， 生成 6β-fluoro-17β-hydroxy-4-androsten-3-one
  参考文献：
  名称：

  卤代类固醇激素的合成—Ⅱ

  摘要：

  用三氟化硼醚化物在胆甾烷，雄烷酮和孕烷系列中裂解3β-乙酰氧基-5α-，6α-环氧化合物，得到相应的3β-乙酰氧基-5α-羟基-6β-氟代化合物。通过适当地操作这些氟代醇，可制得6α-氟胆甾烯酮和具有生物学意义的6α-和6β-氟睾酮以及6α-6β-氟孕酮。

  DOI：

  10.1016/s0040-4020(01)82606-5

文献信息

• Power- and structure-variable fluorinating agents. The N-fluoropyridinium salt system
  作者：Teruo Umemoto、Shinji Fukami、Ginjiro Tomizawa、Kikuko Harasawa、Kosuke Kawada、Kyoichi Tomita

  DOI：10.1021/ja00179a047

  日期：1990.11

  N-Fluoropyridinium salts provide a new system of fluorinating agents by which a wide range of nucleophilic substrates differing in reactivity can be fluorinated due to the varying degree of fluorinating power and also fluorinated very selectively through structural alteration. The scope of selective fluorination should be broadened considerably on the basis of the present results. The N-fluoropyridinium

  N-氟吡啶鎓盐提供了一种新的氟化剂系统，通过该系统，由于氟化能力的不同程度，反应性不同的各种亲核底物可以被氟化，并且还可以通过结构改变非常有选择性地氟化。在现有结果的基础上，选择性氟化的范围应该大大拓宽。因此，N-氟吡啶鎓盐系统应该可以制备许多有用的有机氟化合物
• Synthesis of C-6 fluoroandrogens: Evaluation of ligands for tumor receptor imaging
  作者：Yearn Seong Choe、John A. Katzenellenbogen

  DOI：10.1016/0039-128x(95)00009-f

  日期：1995.5

  Seven androgens, substituted with fluorine at C-6, were prepared as potential imaging agents for androgen receptor-positive prostate tumors and were evaluated in vitro in terms of their lipophilicity and their relative binding affinities (RBA, relative to R 1881 = 100) for the androgen receptor and for sex steroid binding protein. Introduction of a fluorine atom into the C-6 position of an androgen generally decreases binding affinity to the androgen receptor, except in the two cases: 6 alpha-fluoro-19-nor-testosterone (RBA = 41.6 versus 30.6 for the unsubstituted steroid) and 6 alpha-fluoro-19-nor-testosterone (RBA = 8.9 versus 6.6). Receptor binding of the C-6 fluoro-androgens is also stereospecific, showing higher binding affinities for the alpha-epimers compared to the corresponding beta-epimers (4:1-15:1). Binding affinity to sex steroid binding protein is the lowest with 19-nor-testosterone, which is also the least lipophilic androgen studied. Based on the binding properties of compounds in this series, 6 alpha-fluoro-19-nor-testosterone appears to have the most promise as a turner imaging agent.