3β,5α-Dihydroxy-6β-fluorocholestane | 2592-25-8

• 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
• 英文名称: 3β,5α-Dihydroxy-6β-fluorocholestane
• 英文别名: (3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-fluoro-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-5H-cyclopenta[a]phenanthrene-3,5-diol；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-fluoro-10,13-dimethyl-17-((R)-6-methylheptan-2-yl)hexadecahydro-1H-cyclopenta[a]phenanthrene-3,5-diol；6β-fluoro-5α-cholestane-3β,5-diol；6β-Fluor-5α-cholestan-3β,5-diol；(3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-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-3,5-diol
• CAS: 2592-25-8
• 化学式: C₂₇H₄₇FO₂
• 分子量: 422.667
• InChiKey: SEZBGAVATIZVMW-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：

  3β,5α-Dihydroxy-6β-fluorocholestane 生成 6β-Fluor-5α-cholest-2-en-5-ol
  参考文献：
  名称：

  Kocovsky,P.; Cerny,V., Collection of Czechoslovak Chemical Communications, 1978, vol. 43, p. 1933 - 1941

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 三氟化硼乙醚 、 苯 作用下， 生成 3β,5α-Dihydroxy-6β-fluorocholestane
  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

• [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。
• Metal-Free and User-Friendly Regioselective Hydroxyfluorination of Olefins
  作者：Daniel M. Sedgwick、Inés López、Raquel Román、Nanako Kobayashi、Otome E. Okoromoba、Bo Xu、Gerald B. Hammond、Pablo Barrio、Santos Fustero

  DOI：10.1021/acs.orglett.8b00681

  日期：2018.4.20

  inexpensive reagents has been developed. This new approach displays a broader scope than previously reported methodologies and has been applied to the late-stage fluorination of a complex molecule, giving rise to a fluorosteroid derivative. The stereochemistry of the process has also been studied in some detail.

  已经开发出一种简单、用户友好、无金属的方案，用于使用易于获得且廉价的试剂对烯烃进行区域选择性反马尔可夫尼科夫氢氟化。这种新方法比以前报道的方法显示出更广泛的范围，并已应用于复杂分子的后期氟化，从而产生氟类固醇衍生物。该过程的立体化学也已得到一些详细的研究。
• Tetrabutylammonium dihydrogentrifluoride: an efficient catalyst for regio and stereoselective conversion of epoxides to fluorohydrins under solid-liquid phase-transfer catalysis conditions.
  作者：Dario Landini、Michele Penso

  DOI：10.1016/s0040-4039(00)97281-2

  日期：1990.1

  Tetrabutylammonium dihydrogentrifluoride is an efficient and easy-to-handle hydrofluorinating agent in the ring-opening reaction of oxiranes to give good or excellent yields of fluorohydrins under solid-liquid PTC conditions.

  四丁基三氟化氢铵在环氧乙烷的开环反应中是一种高效且易于处理的氢氟化剂，在固液PTC条件下可获得良好或优异的氟代醇收率。
• Steroids. Part X. Boron trifluoride-catalysed rearrangements of 5,6-epoxy-3β-hydroxy- and 5,6-epoxy-3β-methoxy-steroids
  作者：I. G. Guest、B. A. Marples

  DOI：10.1039/j39700001626

  日期：——

  The reactions of 5,6α-epoxy-3β-hydroxy-5α-cholestane, 5,6β-epoxy-3β-hydroxy-5β-cholestane, and 5,6α-epoxy-3β-methoxy-5α-cholestane with boron trifluoride–ether complex in benzene give largely products of rearrangement via C(5)–O cleavage. These results contrast with the known reactions of the corresponding 3β-acetoxy-epoxides which give high yields of fluorohydrins.

  5,6α-环氧-3β-羟基-5α-胆甾烷，5,6β-环氧-3β-羟基-5β-胆甾烷与5,6α-环氧-3β-甲氧基-5α-胆甾烷与三氟化硼-醚的反应苯中的复合物主要通过C（5）-O裂解产生重排产物。这些结果与相应的3β-乙酰氧基-环氧化物的已知反应形成对比，后者给出高产率的氟代醇。
• 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.