4'-(tert-butyl)-5-fluoro-(1,1'-biphenyl)-2-amine | 1183603-21-5

• 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'-(tert-butyl)-5-fluoro-(1,1'-biphenyl)-2-amine
• 英文别名: 5-fluoro-4'-(trifluoromethyl)biphenyl-2-amine；2-Amino-5-fluoro-4'-(trifluoromethyl)biphenyl；4-fluoro-2-[4-(trifluoromethyl)phenyl]aniline
• CAS: 1183603-21-5
• 化学式: C₁₃H₉F₄N
• 分子量: 255.215
• InChiKey: YXWHYIJKXKPGJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4'-(tert-butyl)-5-fluoro-(1,1'-biphenyl)-2-amine 在 盐酸 、 sodium nitrite 、 potassium iodide 作用下， 以 甲醇 、 水 为溶剂， 反应 1.25h， 以73%的产率得到4-(tert-butyl)-5'-fluoro-2'-iodo-1,1'-biphenyl
  参考文献：
  名称：

  A Detailed Study of Acetate-Assisted C–H Activation at Palladium(IV) Centers

  摘要：

  This report describes a detailed investigation of acetate-assisted C-H activation at Pd-IV centers supported by the tris(2-pyridyl)-methane (Py3CH) ligand. Mechanistic information about this transformation has been obtained through the following:, (i) extensive one- and two-dimensional NMR analysis, (ii) reactivity studies of a series of substituted analogues, and (iii) isotope effect studies. These experiments all suggest that C-H activation at [(Py3CH)Pd-IV(biphenyl)Cl-2)(+) occurs via a multistep process involving chloride-to-acetate ligand exchange followed by conformational and configurational isomerization and then C-H cleavage. The data also suggest that C-H cleavage proceeds via an acetate-assisted mechanism with the carboxylate likely serving as an intramolecular base. The viability of acetate-assisted C-H activation at high valent palladium has important implications for the design and optimization of catalytic processes involving this transformation as a key step.

  DOI：

  10.1021/ja401557m
• 作为产物：
  描述：

  2-溴-4-氟苯胺 、 4-叔丁基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 3.0h， 以87%的产率得到4'-(tert-butyl)-5-fluoro-(1,1'-biphenyl)-2-amine
  参考文献：
  名称：

  A Detailed Study of Acetate-Assisted C–H Activation at Palladium(IV) Centers

  摘要：

  This report describes a detailed investigation of acetate-assisted C-H activation at Pd-IV centers supported by the tris(2-pyridyl)-methane (Py3CH) ligand. Mechanistic information about this transformation has been obtained through the following:, (i) extensive one- and two-dimensional NMR analysis, (ii) reactivity studies of a series of substituted analogues, and (iii) isotope effect studies. These experiments all suggest that C-H activation at [(Py3CH)Pd-IV(biphenyl)Cl-2)(+) occurs via a multistep process involving chloride-to-acetate ligand exchange followed by conformational and configurational isomerization and then C-H cleavage. The data also suggest that C-H cleavage proceeds via an acetate-assisted mechanism with the carboxylate likely serving as an intramolecular base. The viability of acetate-assisted C-H activation at high valent palladium has important implications for the design and optimization of catalytic processes involving this transformation as a key step.

  DOI：

  10.1021/ja401557m

文献信息

• Synthesis of phenanthridinones viapalladium-catalyzed C(sp²)–H aminocarbonylation of unprotected o-arylanilines
  作者：Dongdong Liang、Ziwei Hu、Jiangling Peng、Jinbo Huang、Qiang Zhu

  DOI：10.1039/c2cc36817j

  日期：——

  An efficient synthesis of free (NH)-phenanthridinones through Pd-catalyzed C(sp(2))-H aminocarbonylation of unprotected o-arylanilines under an atmospheric pressure of CO has been developed. Some ortho heteroarene substituted anilines as well as N-alkyl protected o-arylanilines are also suitable substrates for this C-H aminocarbonylation reaction.

  有效的合成游离（NH）-菲啶酮通过CO的大气压下未保护的邻芳基苯胺的Pd催化C（sp（2））-H氨基羰基化反应。一些邻杂芳基取代的苯胺以及N-烷基保护的邻芳基苯胺也是该CH氨基羰基化反应的合适底物。
• [EN] 5-HALOGENOPYRAZOLECARBOXAMIDES<br/>[FR] 5-HALOGÉNOPYRAZOLECARBOXAMIDES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2012065947A1

  公开（公告）日：2012-05-24

  The present invention relates to novel 5-halogenopyrazole(thio)carboxamides, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

  本发明涉及一种新型的5-卤代吡唑（硫）酰胺化合物，其制备方法，其作为杀真菌活性剂的用途，特别是以杀真菌组合物的形式，以及使用这些化合物或组合物控制植物病原真菌的方法。
• 5-Halogenopyrazolecarboxamides
  申请人：Benting Jürgen

  公开号：US20130296269A1

  公开（公告）日：2013-11-07

  The present invention relates to novel 5-halogenopyrazole(thio)carboxamides, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

  本发明涉及新型5-卤代吡唑（硫）羧酰胺，其制备方法，其作为杀真菌剂活性剂的用途，特别是以杀真菌剂组合物的形式，以及使用这些化合物或组合物控制植物病原真菌，尤其是植物的方法。
• 5-halogenopyrazolecarboxamides
  申请人：Benting Jürgen

  公开号：US09375004B2

  公开（公告）日：2016-06-28

  The present invention relates to novel 5-halogenopyrazole(thio)carboxamides, their process of preparation, their use as fungicide active agents, particularly in the form of fungicide compositions, and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

  本发明涉及新型的5-卤代吡唑（硫）羧酰胺，它们的制备方法，它们作为杀真菌活性剂的用途，特别是以杀真菌组合物的形式，以及使用这些化合物或组合物对植物病原真菌进行控制的方法。
• 5-HALOGENOPYRAZOLECARBOXAMIDES
  申请人：Bayer Intellectual Property GmbH

  公开号：EP2640707A1

  公开（公告）日：2013-09-25