4-fluoro-N'-(4-pyridyl)benzamide | 113204-25-4

• 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: 4-fluoro-N'-(4-pyridyl)benzamide
• 英文别名: 4-fluoro-N-(pyridin-4-yl)benzamide；4-fluoro-N-pyridin-4-ylbenzamide
• CAS: 113204-25-4
• 化学式: C₁₂H₉FN₂O
• mdl: MFCD00452544
• 分子量: 216.215
• InChiKey: DPMZMSGLJJFLMW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-氨基吡啶 、 对氟苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 4-fluoro-N'-(4-pyridyl)benzamide
  参考文献：
  名称：

  Assembling an isomer grid: the isomorphous 4-, 3- and 2-fluoro-N′-(4-pyridyl)benzamides

  摘要：

  The three title isomers, 4-, (I), 3-, (II), and 2-fluoro-N'-(4-pyridyl) benzamide, (III), all C(12)H(9)FN(2)O, crystallize in the P2(1)/c space group (No. 14) with similar unit-cell parameters and are isomorphous and isostructural at the primary hydrogen-bonding level. An intramolecular C-H center dot center dot center dot O=C interaction is present in all three isomers [C center dot center dot center dot O= 2.8681 (17)-2.884 (2) angstrom and C-H center dot center dot center dot O117-118 angstrom], with an additional N-H center dot center dot center dot F [N center dot center dot center dot F = 2.7544 (15) angstrom] interaction in (III). Intermolecular amide-pyridine N-H center dot center dot center dot N hydrogen bonds link molecules into one-dimensional zigzag chains [ graph set C(6)] along the [ 010] direction as the primary hydrogen bond [N center dot center dot center dot N = 3.022 (2), 3.049 (2) and 3.0213 (17) angstrom]. These are augmented in (I) by C-H center dot center dot center dot pi(arene) and cyclic C-F center dot center dot center dot pi(arene) contacts about inversion centres, in (II) by C-F center dot center dot center dot F-C interactions [C center dot center dot center dot F = 3.037 (2) angstrom] and weaker C-H center dot center dot center dot pi(arene)/C-H center dot center dot center dot F contacts, and in (III) by C-H center dot center dot center dot pi(arene) and C=O center dot center dot center dot O=C interactions, linking the alternating chains into two-dimensional sheets. Typical amide N-H center dot center dot center dot O=C hydrogen bonds [as C(4) chains] are not present [N center dot center dot center dot O = 3.438 (2) angstrom in (I), 3.562 (2) angstrom in (II) and 3.7854 (16) angstrom in (III)]; the C=O group is effectively shielded and only participates in weaker interactions/contacts. This series is unusual as the three isomers are isomorphous (having similar unit-cell parameters, packing and alignment), but they differ in their interactions and contacts at the secondary level.

  DOI：

  10.1107/s0108270108012067

文献信息

• Synthesis of NCA [carbonyl-11C]amides by direct reaction ofin situ generated [11C]carboxymagnesium halides with amines under microwave-enhanced conditions
  作者：Shui-Yu Lu、Jinsoo Hong、Victor W. Pike

  DOI：10.1002/jlcr.786

  日期：2003.11

  No-carrier-added (NCA) aromatic and aliphatic [carbonyl-11C]amides were rapidly (<5 min) synthesized in one pot in useful radiochemical yields (20–65%, decay-corrected) by directly coupling amines with NCA [11C]carboxyhyphenmagnesium halides generated in situ from Grignard reagents and cyclotron-produced [11C]carbon dioxide. In this system cyclohexylcarboxymagnesium chloride (1b) is more reactive than 4-fluorophenylcarboxymagnesium bromide (2b) and primary amines (e.g. aniline, aminopyridines) far more reactive than secondary amines (e.g. 2-(methylamino)pyridine). The scope of the reaction was widened considerably by the application of microwaves, which allowed reactions to be carried out at much higher temperature than the boiling point of the solvent (i.e. tetrahydrofuran, b.p. 67°C). Copyright © 2003 John Wiley & Sons, Ltd.

  无载体的芳香和脂肪族[羰基-11C]酰胺通过直接将胺与NCA [11C]羧酸镁卤化物（由Grignard试剂和回旋加速器产生的[11C]二氧化碳在位生成）耦合，快速（<5分钟）合成，产率有用的放射化学产率（20-65%，衰减校正）。在这个系统中，环己基羧酸镁氯化物（1b）比4-氟苯基羧酸镁溴化物（2b）更具反应性，而伯胺（例如苯胺，氨基吡啶）远比仲胺（例如2-（甲氨基）吡啶）更具反应性。通过应用微波，反应范围大大扩展，微波允许反应在远高于溶剂沸点的温度下进行（即四氢呋喃，沸点67°C）。版权所有 © 2003 John Wiley & Sons, Ltd.