2-fluoro-N'-(4-pyridyl)benzamide | 113204-23-2

• 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: 2-fluoro-N'-(4-pyridyl)benzamide
• 英文别名: 2-fluoro-N-(pyridin-4-yl)benzamide；2-fluoro-N-pyridin-4-ylbenzamide
• CAS: 113204-23-2
• 化学式: C₁₂H₉FN₂O
• mdl: MFCD00454566
• 分子量: 216.215
• InChiKey: CMRRKJCQVVVOIJ-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

• 作为反应物：
  描述：

  2-fluoro-N'-(4-pyridyl)benzamide 在 盐酸 、 O-(三甲基硅)羟胺 、 五氯化磷 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 生成 3-[(4-pyridinyl)amino]-1,2-benzisoxazole
  参考文献：
  名称：

  通过亲核芳香取代反应制备3-（4-吡啶基氨基）-1,2-苯并恶唑

  摘要：

  描述了制备仲3-氨基-1，2-苯并恶唑的有效的三步法。关键步骤是邻卤代或硝基a肟的异构化/环化。亲核取代反应可在芳香环上具有多种取代基，包括对位的对位电子给体取代基，从而获得成功。

  DOI：

  10.1016/0040-4039(95)02361-5
• 作为产物：
  描述：

  4-氨基吡啶 、 邻氟苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-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

• Assembling an isomer grid: the isomorphous 4-, 3- and 2-fluoro-<i>N</i>′-(4-pyridyl)benzamides
  作者：Katie Donnelly、John F. Gallagher、Alan J. Lough

  DOI：10.1107/s0108270108012067

  日期：2008.6.15

  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.
• Preparation of 3-(4-pyridinylamino)-1,2-benzisoxazoles via a nucleophilic aromatic substitution reaction
  作者：David M. Fink、Barbara E. Kurys

  DOI：10.1016/0040-4039(95)02361-5

  日期：1996.2

  of secondary 3-amino-1,2-benzisoxazoles is described. The key step is the isomerization/cyclization of an ortho halo or nitro amidoxime. The nucleophilic substitution reaction is successful with a wide variety of substituents on the aromatic ring, including an electron donating substituent para to the site of attack.

  描述了制备仲3-氨基-1，2-苯并恶唑的有效的三步法。关键步骤是邻卤代或硝基a肟的异构化/环化。亲核取代反应可在芳香环上具有多种取代基，包括对位的对位电子给体取代基，从而获得成功。