2-Fluoroestradiol | 16205-32-6

• 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: 2-Fluoroestradiol
• 英文别名: 2-fluoro-17β-estradiol；2-fluoro-β-estradiol；(8R,9S,13S,14S,17S)-2-fluoro-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
• CAS: 16205-32-6
• 化学式: C₁₈H₂₃FO₂
• 分子量: 290.378
• InChiKey: HDPXSAXRLVDBIR-XSSYPUMDSA-N

物化性质

• 熔点：
  177 °C
• 沸点：
  421.8±45.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Fluoroestradiol 在 potassium nitrososulfonate 、 potassium iodide 作用下， 生成 雌甾-1,3,5(10)-三烯2,3,17-三醇
  参考文献：
  名称：

  Novel synthesis of 2-fluoroestradiol from 19-Cortestosterone: Biomimetic oxidative defluorination to 2-hydroxyestradiol

  摘要：

  A new, short synthetic route to 2-fluoroestradiol from 19-nortestosterone is described which gives the target compound in an approximately 25% overall yield. Oxidative defluorination of 2-fluoroestradiol to 2-hydroxyestradiol via treatment with Frémy's salt/iodide ion is reported. This process is regarded as biomimetic with respect to cytochrome P-450-dependent oxidative defluorination.

  DOI：

  10.1016/0039-128x(89)90058-5
• 作为产物：
  描述：

  19-nortestosterone 在 盐酸 、 正丁基锂 、 水 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 Selectfluor 、 triethylamine tris(hydrogen fluoride) 、 三乙胺 、 二异丙胺 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 21.16h， 生成 2-Fluoroestradiol
  参考文献：
  名称：

  Preparation of o-Fluorophenols from Nonaromatic Precursors: Mechanistic Considerations for Adaptation to Fluorine-18 Radiolabeling

  摘要：

  The preparation of fluorine-18 labeled o-fluorophenols at high specific activity is challenging and requires use of [F-18]fluoride ion as the radioisotope source. As a novel, alternative approach, we found that treatment of alpha-diazocyclohexenones with Selectfluor and Et3N center dot 3HF followed by HF elimination and tautomerization afforded o-fluorophenols regioselectively and rapidly. To adapt this chemistry to F-18 radiolabeling, using bromine electrophiles in place of Selectfluor gave the o-fluorophenol via an alpha-bromo-alpha-fluoroketone intermediate in lower but still reasonable yields.

  DOI：

  10.1021/acs.orglett.5b02640

文献信息

• [EN] ESTRATRIENE DERIVATIVES<br/>[FR] DERIVES D'ESTRATRIENE
  申请人：CRYPTOPHARMA PTY LTD

  公开号：WO2004101595A1

  公开（公告）日：2004-11-25

  Compounds and methods for modulating mesenchymal cell function, for instance smooth muscle and fibroblast proliferation or cytokine expression, and for treating conditions associated with mesenchymal cell function, for instance airway hyperresponsiveness associated with asthma. The compounds also supress inflammation. The compounds are a class of estratriene derivates, and includes various derivatives of 2-methoxyestradiol comprising a group A, including a substituted aromatic substituent in the 2-, 6- or 17- position.

  调节间叶细胞功能的化合物和方法，例如平滑肌和成纤维细胞增殖或细胞因子表达，以及治疗与间叶细胞功能相关的疾病，例如与哮喘相关的气道高反应性。这些化合物还抑制炎症。这些化合物是一类雌三烯衍生物，包括各种2-甲氧基雌二醇衍生物，其中包括A组，包括在2-、6-或17-位置有取代芳香基团。
• Estratriene Derivatives
  申请人：Stewart George Alastair

  公开号：US20070275935A1

  公开（公告）日：2007-11-29

  Compounds and methods for modulating mesenchymal cell function, for instance smooth muscle and fibroblast proliferation or cytokine expression, and for treating conditions associated with mesenchymal cell function, for instance airway hyperresponsiveness associated with asthma. The compounds also suppress inflammation. The compounds are a class of estratriene derivates, and includes various derivatives of 2-methoxyestradiol comprising a group A, including a substituted aromatic substituent in the 2-, 6- or 17-position.

  化合物和方法用于调节间充质细胞功能，例如平滑肌和成纤维细胞增殖或细胞因子表达，并用于治疗与间充质细胞功能相关的疾病，例如与哮喘相关的气道过度反应。这些化合物还可抑制炎症。这些化合物是一类雌三烯衍生物，包括2-甲氧基雌二醇的各种衍生物，其中包括A组，包括2-，6-或17-位取代芳香基取代物。
• Improvements in or relating to the treatment of estrogen deficiency conditions
  申请人：Liehr, Joachim Georg

  公开号：EP0117117A1

  公开（公告）日：1984-08-29

  2-Fluoroestradiol may be used to treat estrogen-deficiency states in human females who have a predisposition to cancer of estrogen sensitive tissue.

  2-氟雌二醇可用于治疗易患雌激素敏感组织癌症的女性的雌激素缺乏症。
• Improved method of preparing 2-Fluoro-17beta-estradiol
  申请人：ELI LILLY AND COMPANY

  公开号：EP0147155A2

  公开（公告）日：1985-07-03

  2-Fluoro-17β-estradiol is synthesized by mercurating at C-2 a 17β-estradiol diester or dietherate, displacing the mercury group with fluorine and then removing the ester- or ether-protecting groups.

  2-Fluoro-17β-estradiol 的合成方法是在 17β-estradiol 二酯或二醚酸酯的 C-2 位进行汞化，用氟取代汞基，然后去除酯或醚保护基。
• Estrogenic compounds as antimitotic agents
  申请人：CHILDREN'S MEDICAL CENTER CORPORATION

  公开号：EP1640009A1

  公开（公告）日：2006-03-29

  The application discloses methods of making medicaments for treating mammalian diseases characterised by abnormal cell mitosis by administering estradiol derivatives including those comprising colchicine or combretastatin A-4 structural motifs of general formulae found above in a dosage sufficient to inhibit cell mitosis. The application discloses novel compounds used in the methods.

  本申请公开了用于治疗以细胞有丝分裂异常为特征的哺乳动物疾病的药物的制造方法，其方法是施用雌二醇衍生物，包括含有上述通式中的秋水仙碱或考布他丁 A-4 结构基团的雌二醇衍生物，其剂量足以抑制细胞有丝分裂。该申请公开了用于上述方法的新型化合物。