4-氟雄甾-4-烯-3,17-二酮 | 98102-30-8

• 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: 4-氟雄甾-4-烯-3,17-二酮
• 英文名称: androst-4-ene-3,17-dione-4-fluoro
• 英文别名: 4-fluoro-4-androstene-3,17-dione；4-fluoroandrost-4-ene-3,17-dione；(8R,9S,10R,13S,14S)-4-fluoro-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthrene-3,17-dione
• CAS: 98102-30-8
• 化学式: C₁₉H₂₅FO₂
• 分子量: 304.405
• InChiKey: QBRBEAIYDMHSJE-KZQROQTASA-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：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  雄烯二酮 在 silica gel 、 fluorine 作用下， 以 乙醇 、 氯仿 、 一氟三氯甲烷 为溶剂， 生成 4-氟雄甾-4-烯-3,17-二酮
  参考文献：
  名称：

  使用元素氟对α，β-不饱和羰基化合物进行氟化

  摘要：

  元素氟成功地跨过各种α，β-不饱和羰基化合物的双键添加。必要的成分是溶剂混合物中存在酒精。不同于所有其他卤素在烯烃中的加成，氟以顺式特异性添加其自身。vic二氟产物易于脱氟化氢以形成相应的α-氟代羰基衍生物。

  DOI：

  10.1016/j.tet.2015.12.004

文献信息

• Solvent dependence of the synthesis and reactions of acetyl hypofluorite
  作者：Shlomo Rozen、Yifat Bareket、Moshe Kol

  DOI：10.1016/s0022-1139(00)80424-8

  日期：1993.3

  Acetyl hypofluorite (AcOF) has been previously prepared using CFCl3 (CFC-11) as a solvent. It was found that acetonitrile can replace trichlorofluoromethane without sacrificing the efficiency and the regio- and stereo-selectivity of the addition of AcOF to olefins. Most other solvents tested proved to be inadequate for the synthesis of AcOF, despite the fact that fluorine does react with the dispersed

  先前已使用CFCl 3（CFC-11）作为溶剂制备了乙炔基次萤石（AcOF）。发现乙腈可以代替三氯氟甲烷，而不会牺牲向烯烃中添加AcOF的效率以及区域和立体选择性。尽管氟确实会与溶剂中存在的分散乙酸钠发生反应，但事实证明，大多数测试的其他溶剂不足以合成AcOF。
• METHODS AND AGENTS FOR TREATING TUBERCULOSIS
  申请人：Eltis Lindsay D.

  公开号：US20100041631A1

  公开（公告）日：2010-02-18

  The present invention relates to the treatment of tuberculosis (mycobacterial infections) by the use of KshAB complex inhibitors, or a KstD molecule, or a HsaAB complex, or a HsaC molecule, or a HsaD molecule. The application also includes a method for identifying an inhibitor or modulator of the previously mentioned molecules and complexes.

  本发明涉及使用KshAB复合物抑制剂、KstD分子、HsaAB复合物、HsaC分子或HsaD分子治疗结核病（分枝杆菌感染）。该申请还包括一种鉴定前述分子和复合物的抑制剂或调节剂的方法。
• Electrophilic fluorination of unsaturated systems with the recently developed acetyl hypofluorite
  作者：Shlomo Rozen、Ori Lerman、Moshe Kol、David Hebel

  DOI：10.1021/jo00224a019

  日期：1985.11
• Hodson, Harold F.; Madge, David J.; Widdowson, David A., Journal of the Chemical Society. Perkin transactions I, 1995, # 23, p. 2965 - 2968
  作者：Hodson, Harold F.、Madge, David J.、Widdowson, David A.

  DOI：——

  日期：——
• Synthesis and evaluation of analogues of 4-androstene-3,17-dione as aromatase inhibitors
  作者：Martin G. Rowlands、Allan B. Foster、John Mann、Barbara Pietrzak、Jessica Wilkinson、R.Charles Coombes

  DOI：10.1016/0039-128x(87)90011-0

  日期：1987.4

  Twenty-three synthetic analogues of 4-androstene-3,17-dione (androstenedione) have been evaluated as inhibitors of human placental microsomal aromatase enzyme. Among the most potent of these compounds were the 4-hydroxy, 6 alpha-fluoro, 6 beta-fluoro, and 4-fluoroandrostenediones and 4-fluoro-19-nor-4-androstene-3,17-dione. 4-Hydroxy-4-androstene-3,17-dione (4HAD) is an irreversible inhibitor of aromatase in vitro, whereas the four fluoro analogues are reversible inhibitors. 4HAD and 4-fluoro-4-androstene-3,17-dione caused significant regression of the nitrosomethylurea-induced mammary tumor in rats, but the other fluoro derivatives were inactive.