4-(2-fluorophenyl)-2,5-dimethylpyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(2-fluorophenyl)-2,5-dimethylpyridine
• 化学式: C₁₃H₁₂FN
• 分子量: 201.243
• InChiKey: RLCVFWSWDFPDCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-(2-fluorophenyl)but-3-en-2-one 、 propargyl azide 在 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 24.5h， 以146 mg的产率得到4-(2-fluorophenyl)-2,5-dimethylpyridine
  参考文献：
  名称：

  Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy

  摘要：

  An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6 pi-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.

  DOI：

  10.1021/acs.orglett.5b02903

文献信息

• 7-(Pyridinyl)-/-alkyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid having antibacterial activity and preparation thereof
  申请人：STERLING DRUG INC.

  公开号：EP0179239A2

  公开（公告）日：1986-04-30

  1-Ethyt-6-ftuoro-1,4-dihydro-7-(2,6-dimethy)-4-pyridinyt)-4-oxo-3-quinolinecarboxylic acid or salt thereof, a novel compound useful highly potent antibacterial agent with a broad spectrum of anti-microbial activity, is prepared by nitrating the corresponding 6-desfluoro compound to produce the corresponding 6-nitro compound, reducing the latter compound to produce the corresponding 6-amino compound and converting the 6-amino via its diazonium salt to said 6-fluoro compound. Said novel acid is also prepared via intermediates prepared by heating 4-(2-fluorophenyl)-2,6-dimethyl-3,5-pyridinedicarboxylic acid to produce a mixture of 4-(2-fluorophenyl)-2,6-di-methylpyridine and 2,4-dimethyl-5H-[1]benzopyrano[3,4-c)pyridin-5-one, separating the components of said mixture and nitrating 4-(2-fluorophenyl)-2,6-dimethylpyridine to produce 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine.

  1-乙基-6-氟-1,4-二氢-7-(2,6-二甲基)-4-吡啶)-4-氧代-3-喹啉羧酸或其盐是一种新型化合物，是一种具有广谱抗微生物活性的高效抗菌剂、其制备方法是：硝化相应的 6-去氟化合物，生成相应的 6-硝基化合物；还原后者，生成相应的 6-氨基化合物；然后通过重氮盐将 6-氨基化合物转化为所述 6-氟化合物。所述新型酸也可以通过加热 4-(2-氟苯基)-2,6-二甲基-3,5-吡啶二羧酸生成 4-(2-氟苯基)-2,6-二甲基吡啶和 2、4-(2-氟苯基)-2,6-二甲基吡啶和 2,4-二甲基-5H-[1]苯并吡喃并[3,4-c]吡啶-5-酮的混合物，分离所述混合物的组分并硝化 4-(2-氟苯基)-2,6-二甲基吡啶，生成 4-(2-氟-5-硝基苯基)-2,6-二甲基吡啶。
• Synthesis of Polysubstituted Pyridines via a One-Pot Metal-Free Strategy
  作者：Hongbo Wei、Yun Li、Ke Xiao、Bin Cheng、Huifei Wang、Lin Hu、Hongbin Zhai

  DOI：10.1021/acs.orglett.5b02903

  日期：2015.12.18

  An efficient strategy for the one-pot synthesis of polysubstituted pyridines via a cascade reaction from aldehydes, phosphorus ylides, and propargyl azide is reported. The reaction sequence involves a Wittig reaction, a Staudinger reaction, an aza-Wittig reaction, a 6 pi-3-azatriene electrocyclization, and a 1,3-H shift. This protocol provides quick access to the polysubstituted pyridines from readily available substrates in good to excellent yields.