N'-(4-fluorophenyl)-N,N-dimethylacetamidine | 94793-29-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N'-(4-fluorophenyl)-N,N-dimethylacetamidine
• 英文别名: N'-(4-fluoro-phenyl)-N,N-dimethyl-acetamidine；N'-(4-fluorophenyl)-N,N-dimethylethanimidamide
• CAS: 94793-29-0
• 化学式: C₁₀H₁₃FN₂
• 分子量: 180.225
• InChiKey: FBMSXVILQYIGIO-UHFFFAOYSA-N

物化性质

• 沸点：
  240.642±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  0.997±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)
• 保留指数：
  1465

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N'-(4-fluorophenyl)-N,N-dimethylacetamidine 在 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium periodate 、 copper(l) iodide 、 硫酸 、 碘 、 potassium carbonate 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 、 甲醇 、 水 为溶剂， 反应 10.67h， 生成 1-(4-fluorophenyl)-2,5-dimethyl-4-o-tolylethynyl-1H-imidazole
  参考文献：
  名称：

  A Safe and Efficient Synthetic Route to a 2,5-Dimethyl-1-aryl-1H-imidazole Intermediate

  摘要：

  An optimized route to an iodo-imidazole intermediate in the synthesis of 4-ethynyl-2,5-dimethyl-1-aryl-1H-imidazoles (6) was devised. Important data for the optimization work was obtained by carrying out a DOE study to gain understanding of the parameters that affect the key intramolecular cyclization to build the imidazole ring. Additional information on the reaction mechanism of this step was obtained by carrying out a flow NMR experiment. In order to complete the proof of concept, the iodo-imidazole intermediate was converted to two ethynyl imidazoles (6a, b) using metal-catalyzed reactions.

  DOI：

  10.1021/op100335q
• 作为产物：
  描述：

  1,1-二甲氧基-N,N-二甲基乙胺 、 4-氟苯胺 以100%的产率得到N'-(4-fluorophenyl)-N,N-dimethylacetamidine
  参考文献：
  名称：

  A Safe and Efficient Synthetic Route to a 2,5-Dimethyl-1-aryl-1H-imidazole Intermediate

  摘要：

  An optimized route to an iodo-imidazole intermediate in the synthesis of 4-ethynyl-2,5-dimethyl-1-aryl-1H-imidazoles (6) was devised. Important data for the optimization work was obtained by carrying out a DOE study to gain understanding of the parameters that affect the key intramolecular cyclization to build the imidazole ring. Additional information on the reaction mechanism of this step was obtained by carrying out a flow NMR experiment. In order to complete the proof of concept, the iodo-imidazole intermediate was converted to two ethynyl imidazoles (6a, b) using metal-catalyzed reactions.

  DOI：

  10.1021/op100335q

文献信息

• A Safe and Efficient Synthetic Route to a 2,5-Dimethyl-1-aryl-1<i>H</i>-imidazole Intermediate
  作者：Ana C. Barrios Sosa、R. Thomas Williamson、Ryan Conway、Ashish Shankar、Rosline Sumpter、Thomas Cleary

  DOI：10.1021/op100335q

  日期：2011.3.18

  An optimized route to an iodo-imidazole intermediate in the synthesis of 4-ethynyl-2,5-dimethyl-1-aryl-1H-imidazoles (6) was devised. Important data for the optimization work was obtained by carrying out a DOE study to gain understanding of the parameters that affect the key intramolecular cyclization to build the imidazole ring. Additional information on the reaction mechanism of this step was obtained by carrying out a flow NMR experiment. In order to complete the proof of concept, the iodo-imidazole intermediate was converted to two ethynyl imidazoles (6a, b) using metal-catalyzed reactions.