2-{4'-[(Diethoxyphosphoryl)difluoromethyl]phenyl}-1-methylpyrrole-5-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-{4'-[(Diethoxyphosphoryl)difluoromethyl]phenyl}-1-methylpyrrole-5-carbaldehyde
• 英文别名: Gkyxatxsjqaand-uhfffaoysa-；5-[4-[diethoxyphosphoryl(difluoro)methyl]phenyl]-1-methylpyrrole-2-carbaldehyde
• 化学式: C₁₇H₂₀F₂NO₄P
• 分子量: 371.321
• InChiKey: GKYXATXSJQAAND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  57.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 在 bis-triphenylphosphine-palladium(II) chloride 锌 作用下， 以 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.5h， 生成 2-{4'-[(Diethoxyphosphoryl)difluoromethyl]phenyl}-1-methylpyrrole-5-carbaldehyde
  参考文献：
  名称：

  Facile syntheses of building blocks for the construction of phosphotyrosine mimetics

  摘要：

  横松和渋谷描述的铜催化锌膦酸酯化学可用于通过斯蒂尔（Stille）和铃木-宫浦（Suzuki-Miyaura）偶联反应进入经典的金属有机偶联反应领域。1,4-二碘苯在铜(I)催化下与由二乙基溴二氟甲基膦酸酯衍生的有机锌试剂发生偶联，生成二乙基(4-碘苯基)二氟甲基膦酸酯。与(4-三氟甲磺酰氧基)和(4-九氟丁磺酰氧基)碘苯进行的偶联反应产率更高。碘化物和三氟甲磺酸酯在钯催化条件下与一系列锡烷和硼酸发生偶联，产率从中等到优异。渋谷-横松偶联反应在具有更丰富官能团的碘芳烃和杂芳烃上也取得了成功，这些重要磷酸类似物被引入多种骨架上。

  DOI：

  10.1039/b004187o

文献信息

• Facile syntheses of aryldifluorophosphonate building blocks
  作者：G.Stuart Cockerill、Howard J. Easterfield、Jonathan M. Percy

  DOI：10.1016/s0040-4039(99)00266-x

  日期：1999.3

  The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used directly in the synthesis of phosphotyrosine analogue F(2)Pmp, and in entering the classical organometallic coupling repertoire via Stille and Suzuki-Miyaura couplings. Herein, we report a streamlined synthesis of F(2)Pmp, and of a pivotal triflate, which undergoes a range of palladium-catalysed couplings with aryl and heteroaryl components. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Facile syntheses of building blocks for the construction of phosphotyrosine mimetics
  作者：G. Stuart Cockerill、Howard J. Easterfield、Jonathan M. Percy、Stéphane Pintat

  DOI：10.1039/b004187o

  日期：——

  The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used to enter the classical organometallic coupling repertoire via Stille and Suzuki–Miyaura couplings. 1,4-Diiodobenzene underwent coupling with the organozinc reagent derived from diethyl bromodifluoromethylphosphonate with copper(I) catalysis to afford diethyl (4-iodophenyl)difluoromethylphosphonate. Higher yielding couplings were run with (4-trifluoromethylsulfonyloxy)- and (4-nonafluorobutylsulfonyloxy)-iodobenzenes. The iodide and the triflate coupled under palladium-catalysed conditions with a range of stannanes and boronic acids in moderate to excellent yields. Shibuya–Yokomatsu couplings were also successful with more functionalised iodoarenes and heteroarenes presenting the important phosphate mimic on a range of scaffolds.

  横松和渋谷描述的铜催化锌膦酸酯化学可用于通过斯蒂尔（Stille）和铃木-宫浦（Suzuki-Miyaura）偶联反应进入经典的金属有机偶联反应领域。1,4-二碘苯在铜(I)催化下与由二乙基溴二氟甲基膦酸酯衍生的有机锌试剂发生偶联，生成二乙基(4-碘苯基)二氟甲基膦酸酯。与(4-三氟甲磺酰氧基)和(4-九氟丁磺酰氧基)碘苯进行的偶联反应产率更高。碘化物和三氟甲磺酸酯在钯催化条件下与一系列锡烷和硼酸发生偶联，产率从中等到优异。渋谷-横松偶联反应在具有更丰富官能团的碘芳烃和杂芳烃上也取得了成功，这些重要磷酸类似物被引入多种骨架上。