(R)-cholesterol 2-fluoro-2-(4-methoxyphenyl)acetate | 1205648-19-6

• 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: (R)-cholesterol 2-fluoro-2-(4-methoxyphenyl)acetate
• 英文别名: [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (2R)-2-fluoro-2-(4-methoxyphenyl)acetate
• CAS: 1205648-19-6
• 化学式: C₃₆H₅₃FO₃
• 分子量: 552.813
• InChiKey: YTRCLYUEQBDBPK-QKNIFUGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.2
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胆固醇 、 4-甲氧基苯乙酰氯 在 bis-triphenylphosphine-palladium(II) chloride 、 benzoylquinidine 、 N-氟代双苯磺酰胺 、 N,N-二异丙基乙胺 、 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以77%的产率得到(R)-cholesterol 2-fluoro-2-(4-methoxyphenyl)acetate
  参考文献：
  名称：

  Combining Asymmetric Catalysis with Natural Product Functionalization through Enantioselective α-Fluorination

  摘要：

  An examination into the derivatization of various natural products using newly developed alpha-fluorination methodology is disclosed. An activated ketene enolate, generated from in acid chloride, is allowed to react with an electrophilic fluorine source (NFSi). Quenching the reaction with a nucleophilic natural product produces biologically relevant alpha-fluorinated carbonyl derivatives of select chemotherapeutics, antibiotics, and other pharmaceuticals.

  DOI：

  10.1021/jo9024072

文献信息

• Combining Asymmetric Catalysis with Natural Product Functionalization through Enantioselective α-Fluorination
  作者：Jeremy Erb、Ethan Alden-Danforth、Nathan Kopf、Michael T. Scerba、Thomas Lectka

  DOI：10.1021/jo9024072

  日期：2010.2.5

  An examination into the derivatization of various natural products using newly developed alpha-fluorination methodology is disclosed. An activated ketene enolate, generated from in acid chloride, is allowed to react with an electrophilic fluorine source (NFSi). Quenching the reaction with a nucleophilic natural product produces biologically relevant alpha-fluorinated carbonyl derivatives of select chemotherapeutics, antibiotics, and other pharmaceuticals.