(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-fluoro-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol | 4447-87-4

• 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: (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-fluoro-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
• 英文别名: (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-fluoro-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,6-diol
• CAS: 4447-87-4
• 化学式: C₂₇H₄₇FO₂
• 分子量: 422.667
• InChiKey: ZXFSNDQRTQDMLA-RUXQDQFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-fluoro-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol 在 chromium(VI) oxide 作用下， 以 丙酮 为溶剂， 生成 5α-Fluorcholestan-3,6-dion
  参考文献：
  名称：

  亚硝酰氟与所选甾体烯的反应。δ-5-4-酮类固醇的新合成。

  摘要：

  DOI：

  10.1021/jo01274a005
• 作为产物：
  描述：

  5-fluoro-5α-cholestane-3β,6β-diol diacetate 在 甲醇 、 氢氧化钾 作用下， 以 乙醚 为溶剂， 反应 1.0h， 生成 (3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-fluoro-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
  参考文献：
  名称：

  Ishiguro, Masaji; Saito, Hiromitsu; Ikekawa, Nobuo, Journal of the Chemical Society. Perkin transactions I, 1980, p. 2507 - 2510

  摘要：

  DOI：

文献信息

• [EN] HALOGENATED CHOLESTEROL ANALOGUES AND METHODS OF MAKING AND USING SAME<br/>[FR] ANALOGUES HALOGÉNÉS DU CHOLESTÉROL ET LEURS PROCÉDÉS DE PRÉPARATION ET LEURS MÉTHODES D'UTILISATION
  申请人：UNIV MICHIGAN REGENTS

  公开号：WO2020069267A1

  公开（公告）日：2020-04-02

  Provided herein are halogenated cholesterol analogues, including methods of making and using the same. Also provided are methods of making radiolabeled cholesterol analogues including admixing an epoxide with a fluorine-18 source under conditions to form a radiofluorinated cholesterol analogue.

  本文提供了卤代胆固醇类似物，包括其制备和使用方法。还提供了制备放射标记胆固醇类似物的方法，包括在条件下将环氧化合物与氟-18源混合以形成放射氟标记的胆固醇类似物。
• Ring opening of epoxides with [¹⁸F]FeF species to produce [¹⁸F]fluorohydrin PET imaging agents
  作者：Stefan Verhoog、Allen F. Brooks、Wade P. Winton、Benjamin L. Viglianti、Melanie S. Sanford、Peter J. H. Scott

  DOI：10.1039/c9cc02779c

  日期：——

  This report describes a simple technique for the preparation of [¹⁸F]HF and its application to the generation of an [¹⁸F]FeF species for opening sterically hindered epoxides. This easily automated one-pot procedure has been successfully employed to prepare four drug-like molecules in good yields and high molar activities, including 5-[¹⁸F]fluoro-6-hydroxy-cholesterol.

  这份报告描述了一种简单的技术，用于制备 [¹⁸F]HF 并将其应用于生成 [¹⁸F]FeF 物种以打开立体阻碍的环氧化物。这种易于自动化的一锅法已成功地用于制备四种药物类分子，产率高，摩尔活性高，包括 5-[¹⁸F]氟-6-羟基胆固醇。
• 960. Aspects of stereochemistry. Part IX. The formation of fluorohydrins from the cholesterol 5 : 6-epoxides and boron trifluoride–ether complex
  作者：H. B. Henbest、T. I. Wrigley

  DOI：10.1039/jr9570004765

  日期：——
• Halogenated Cholesterol Analogues and Methods of Making and Using Same
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20210355154A1

  公开（公告）日：2021-11-18

  Provided herein are halogenated cholesterol analogues, including methods of making and using the same. Also provided are methods of making radiolabeled cholesterol analogues including admixing an epoxide with a fluorine-18 source under conditions to form a radiofluorinated cholesterol analogue.