(2R*,3R*)-2-bromo-3-fluoro-3-(1-trityl-1H-imidazol-4-yl)propan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (2R*,3R*)-2-bromo-3-fluoro-3-(1-trityl-1H-imidazol-4-yl)propan-1-ol
• 英文别名: (2S,3S)-2-bromo-3-fluoro-3-(1-tritylimidazol-4-yl)propan-1-ol
• 化学式: C₂₅H₂₂BrFN₂O
• 分子量: 465.365
• InChiKey: ISHWQWFURBLYBA-LADGPHEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-三苯甲基咪唑-4-甲醛 在 N-溴代丁二酰亚胺(NBS) 、 二异丁基氢化铝 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 (2R*,3R*)-2-bromo-3-fluoro-3-(1-trityl-1H-imidazol-4-yl)propan-1-ol
  参考文献：
  名称：

  New Building Blocks for Fluorinated Bioimidazole Derivatives II:  Preparation of β-Fluorourocanic Acids

  摘要：

  Replacement of vinyl hydrogen with fluorine is based on addition of an FBr equivalent to a double bond followed by HBr elimination. This sequence has been adapted to prepare 3-fluoro-3-imidazolyl-propenoic acids (beta-fluorourocanic acids), and the related fluorinated imidazolyl propenals and prop-2-en-1-ols, from urocanic acid. Tritylation of the imidazole nitrogen was necessary for successful addition of "FBr" to the double bond, and prior reduction of the carboxyl group to the alcohol was required to provide the desired chemoselectivity in the elimination of HX. Reoxidation and deprotection produced the fluorinated urocanic acids.

  DOI：

  10.1021/jo0200419

文献信息

• New Building Blocks for Fluorinated Bioimidazole Derivatives II:  Preparation of β-Fluorourocanic Acids
  作者：Bohumil Dolensky、Kenneth L. Kirk

  DOI：10.1021/jo0200419

  日期：2002.5.1

  Replacement of vinyl hydrogen with fluorine is based on addition of an FBr equivalent to a double bond followed by HBr elimination. This sequence has been adapted to prepare 3-fluoro-3-imidazolyl-propenoic acids (beta-fluorourocanic acids), and the related fluorinated imidazolyl propenals and prop-2-en-1-ols, from urocanic acid. Tritylation of the imidazole nitrogen was necessary for successful addition of "FBr" to the double bond, and prior reduction of the carboxyl group to the alcohol was required to provide the desired chemoselectivity in the elimination of HX. Reoxidation and deprotection produced the fluorinated urocanic acids.