4-(4-Fluoro-phenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(4-Fluoro-phenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid
• 英文别名: 4-(4-fluorophenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid
• 化学式: C₁₃H₁₂FN₃O₂
• mdl: MFCD04448840
• 分子量: 261.256
• InChiKey: VUXDARVRKCNAKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-Fluoro-phenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 以81%的产率得到
  参考文献：
  名称：

  摘要：

  4-Phenyl derivatives of spinaceamine and spinacine undergo mild catalytic hydrogenation under atmospheric pressure with cleavage of the C-4-N-5 bond to give 5-benzyl-substituted histamines and histidines. The process is likely to be facilitated by the double benzylic effect on the C-N bond of the imidazole and benzene rings.

  DOI：

  10.1023/a:1012346021943
• 作为产物：
  描述：

  对氟苯甲醛 、 L-组氨酸 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以65%的产率得到4-(4-Fluoro-phenyl)-4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine-6-carboxylic acid
  参考文献：
  名称：

  摘要：

  4-Phenyl derivatives of spinaceamine and spinacine undergo mild catalytic hydrogenation under atmospheric pressure with cleavage of the C-4-N-5 bond to give 5-benzyl-substituted histamines and histidines. The process is likely to be facilitated by the double benzylic effect on the C-N bond of the imidazole and benzene rings.

  DOI：

  10.1023/a:1012346021943

文献信息

• An Efficient Synthesis of 4(5)-Benzyl-l-histidines Employing Catalytic Transfer Hydrogenolysis at Elevated Temperatures
  作者：D. Smith、Audrey Gallagher、Vincent Crowley、Wayne Gergens、Peter Abel、Martin Hulce

  DOI：10.1055/s-0033-1340462

  日期：——

  An efficient two-step synthesis of 4(5)-benzyl-L-histidine from L-histidine was developed. A Pictet-Spengler reaction between L-histidine and benzaldehyde in the presence of excess strong base yielded 4-L-phenylspinacine within one hour. Catalytic transfer hydrogenolysis in methanol at reflux using ammonium formate rapidly converted 4-L-phenylspinacine to 4(5)-benzyl-L-histidine within five minutes. No racemization of the final product 4(5)-benzyl-L-histidine was observed using the Marfey reagent. To show the utility of this method, a series of fluorinated benzylhistidines were prepared.
• ——
  作者：Yu. M. Yutilov、M. G. Abramyants、N. N. Smolyar

  DOI：10.1023/a:1012346021943

  日期：——

  4-Phenyl derivatives of spinaceamine and spinacine undergo mild catalytic hydrogenation under atmospheric pressure with cleavage of the C-4-N-5 bond to give 5-benzyl-substituted histamines and histidines. The process is likely to be facilitated by the double benzylic effect on the C-N bond of the imidazole and benzene rings.