2-氟-N-(2-碘苯基)苯甲酰胺 | 326902-16-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-氟-N-(2-碘苯基)苯甲酰胺
• 英文名称: 2-fluoro-N-(2-iodophenyl)benzamide
• CAS: 326902-16-3
• 化学式: C₁₃H₉FINO
• mdl: MFCD00763780
• 分子量: 341.123
• InChiKey: WIMRNRJNEGSEKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氟-N-(2-碘苯基)苯甲酰胺 在 copper acetylacetonate 、 乙醇 、 二乙胺 、 vasicine 作用下， 反应 12.0h， 以70%的产率得到2-氟苯甲酰苯胺
  参考文献：
  名称：

  Exploration of Cu-catalyzed regioselective hydrodehalogenation of o-haloanilides using EtOH as hydrogen source

  摘要：

  DOI：

  10.1016/j.jorganchem.2021.121844
• 作为产物：
  描述：

  2-碘苯胺 、 alkaline earth salt of/the/ methylsulfuric acid 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以90%的产率得到2-氟-N-(2-碘苯基)苯甲酰胺
  参考文献：
  名称：

  Intermolecular coupling of 2-iodoanilides with benzoxazoles: synthesis of N-(2-Benzoxazol-2-ylphenyl)benzamides via C–H activation

  摘要：

  Using CuI/xantphos/Pd(OAc)(2) catalytic system, the intermolecular C-C cross coupling between benzoxazoles and ortho-haloanilides has been developed in moderate to good yields. The procedure tolerates a series of functional groups on benzoxazole, such as ester, chloro, methyl, and methoxy groups. This divergent approach provides access to various N-(2-Benzoxazol-2-ylphenyl)amides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.01.150

文献信息

• Copper-catalyzed regioselective 2-amination of o-haloanilides with aqueous ammonia
  作者：Yan-Ling Tang、Mei-Ling Li、Jin-Chun Gao、Yun Sun、Lu Qu、Feng Huang、Ze-Wei Mao

  DOI：10.1016/j.tetlet.2021.153001

  日期：2021.4

  An efficient Cu(II)-vasicine catalytic system has been developed for intramolecular CN bond formation. In this way, regioselective 2-amination of o-haloanilides with aqueous ammonia in EtOH has been achieved. This strategy provides several advantages, such as good regioselectivity, high yields and functional group tolerance.

  已经开发出用于分子内C N键形成的有效Cu（II）-水杨碱催化体系。以这种方式，已经实现了在EtOH中用氨水进行邻卤代苯胺的区域选择性2-胺化。该策略具有几个优点，例如良好的区域选择性，高产率和官能团耐受性。
• Role of Hetero-Halogen (F···X, X = Cl, Br, and I) or Homo-Halogen (X···X, X = F, Cl, Br, and I) Interactions in Substituted Benzanilides
  作者：Susanta K. Nayak、M. Kishore Reddy、Tayur N. Guru Row、Deepak Chopra

  DOI：10.1021/cg101544z

  日期：2011.5.4

  A series of halogen-substituted benzanilides have been synthesized and characterized, and crystallization studies directed toward generation of polymorphs have been performed to delineate the importance of interactions involving halogens. The effect of halogen substitution on the molecular conformation and supramolecular packing has been investigated. The N-H center dot center dot center dot O H-bond is a key structure-directing element acting in conjunction with C-H center dot center dot center dot O and C-H center dot center dot center dot pi interactions. In addition, it is of importance to note that organic fluorine prefers Type I F center dot center dot center dot F contacts, whereas Cl, Br, and I prefer Type II contacts. Hetero-halogen center dot center dot center dot halogen interactions on the other hand are predominately of Type II geometry, and this is due to the greater polarizability of the electron density associated with the heavier halogens. It is of importance to evaluate the contributing role of these interactions in crystal structure packing and the co-operativity associated with such interactions in the solid state.
• Iron-Catalyzed Intramolecular <i>O</i>-Arylation: Synthesis of 2-Aryl Benzoxazoles
  作者：Julien Bonnamour、Carsten Bolm

  DOI：10.1021/ol800744y

  日期：2008.7.3

  A practical iron-catalyzed intramolecular O-arylation reaction and its application in the synthesis of benzoxazole derivatives, starting from the readily available 2-haloanilines, is presented. The key cyclization step involves the use of a combination of the cheap and environmentally friendly FeCl3 and 2,2,6,6-tetramethyl-3,5 heptanedione (TMHD) as the catalyst system.
• Intermolecular coupling of 2-iodoanilides with benzoxazoles: synthesis of N-(2-Benzoxazol-2-ylphenyl)benzamides via C–H activation
  作者：Swarnendu Sasmal、Indira Sen、Roger G. Hall、Sitaram Pal

  DOI：10.1016/j.tetlet.2015.01.150

  日期：2015.3

  Using CuI/xantphos/Pd(OAc)(2) catalytic system, the intermolecular C-C cross coupling between benzoxazoles and ortho-haloanilides has been developed in moderate to good yields. The procedure tolerates a series of functional groups on benzoxazole, such as ester, chloro, methyl, and methoxy groups. This divergent approach provides access to various N-(2-Benzoxazol-2-ylphenyl)amides. (C) 2015 Elsevier Ltd. All rights reserved.
• Exploration of Cu-catalyzed regioselective hydrodehalogenation of o-haloanilides using EtOH as hydrogen source
  作者：Min-Xin Li、Mei-Ling Li、Yan-Ling Tang、Yun Sun、Lu Qu、Feng Huang、Ze-Wei Mao

  DOI：10.1016/j.jorganchem.2021.121844

  日期：2021.6