(Z)-3-fluoro-3-(1-trityl-1H-imidazol-4-yl)prop-2-en-1-ol | 438206-68-9

• 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: (Z)-3-fluoro-3-(1-trityl-1H-imidazol-4-yl)prop-2-en-1-ol
• 英文别名: (Z)-3-fluoro-3-(1-tritylimidazol-4-yl)prop-2-en-1-ol
• CAS: 438206-68-9
• 化学式: C₂₅H₂₁FN₂O
• 分子量: 384.453
• InChiKey: PUJQDEATAXNPGC-KQWNVCNZSA-N

物化性质

• 沸点：
  555.4±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  38
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-3-fluoro-3-(1-trityl-1H-imidazol-4-yl)prop-2-en-1-ol 在 盐酸 、 manganese(IV) oxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 异丁烯 作用下， 以 二氯甲烷 、 溶剂黄146 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (Z)-3-fluoro-3-(1H-imidazol-4-yl)acrylic acid dihydrochloride
  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
• 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 29.0h， 生成 (Z)-3-fluoro-3-(1-trityl-1H-imidazol-4-yl)prop-2-en-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 approaches to side-chain fluorinated bioimidazoles: 4-alkynylimidazoles as substrates for fluorination
  作者：Bohumil Dolensky、Kenneth L Kirk

  DOI：10.1016/s0022-1139(03)00197-0

  日期：2003.11

  3b met with failure. Reduction of the ester gave the hydroxymethyl-substituted acetylene 4. Addition of “FBr” to this substrate and reductive removal of bromine from the product produced fluoroolefins 12, precursors to E- and Z-β-fluorourocanic acids. The same fluoroolefins can be used as intermediates in the synthesis of β-fluorohistidinols.

  已经制备了4-炔基咪唑，并且已经研究了它们作为“ FBr”添加底物（NBS + Et 3 N·3HF）的行为。容易Markownikov除了ethylnylimidazole 2得到fluorobromoolefin 9A，对于2-咪唑基-2-氟-1-乙烯基部分的电势的合成子。2的锂盐与草酸二乙酯反应生成咪唑基丙炔酸酯3b。但是，由于酯官能团的失活作用，所有试图向3b中添加“ FBr”的尝试都失败了。酯的还原得到羟甲基取代的乙炔4。向该底物添加“ FBr”，并从产物中还原除去溴，制得氟代烯烃12，氟代烯烃12是E-和Z -β-氟尿烷酸的前体。相同的氟代烯烃可以用作合成β-氟组氨酸的中间体。