N-(5-氟-2-甲基苯基)-2-吡啶甲酰胺 | 793730-31-1

• 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: N-(5-氟-2-甲基苯基)-2-吡啶甲酰胺
• 中文别名: 二甲基{2-[5-(1H-1,2,4-三唑-1-基甲基)-1H-吲哚-3-基]乙基}胺氧化
• 英文名称: N-(5-fluoro-2-methylphenyl)picolinamide
• 英文别名: N-(5-fluoro-2-methylphenyl)pyridine-2-carboxamide
• CAS: 793730-31-1
• 化学式: C₁₃H₁₁FN₂O
• 分子量: 230.242
• InChiKey: AWKHPGKJGTXKAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  对碘苯甲酸乙酯 、 N-(5-氟-2-甲基苯基)-2-吡啶甲酰胺 在 氧气 、 silver(I) acetate 、 palladium diacetate 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以86%的产率得到ethyl 4-(4-fluoro-2-(picolinamido)benzoyl)benzoate
  参考文献：
  名称：

  Pd-Catalyzed Arylation/Oxidation of Benzylic C–H Bond

  摘要：

  A palladium-catalyzed benzylic C-H arylation/oxidation reaction leading to diaryl ketones has been accomplished. The indispensable role of the bidentate system is disclosed for this sequential process. This chemistry offers a direct new access to a range of diarylketones.

  DOI：

  10.1021/ol300037p
• 作为产物：
  描述：

  2-吡啶甲酸 、 5-氟-2-甲基苯胺 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以77%的产率得到N-(5-氟-2-甲基苯基)-2-吡啶甲酰胺
  参考文献：
  名称：

  通过钯催化多个C–H键官能化合成苄基酯

  摘要：

  通过双齿指导基团辅助多个C（sp 3）-H键的官能化，开发了一种高效，选择性地通过钯催化合成苄基酯的方法。

  DOI：

  10.1021/acs.orglett.5b02518

文献信息

• Synthesis of Benzyl Esters via Functionalization of Multiple C–H Bonds by Palladium Catalysis
  作者：Danyang Li、Ming Yu、Jitan Zhang、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1021/acs.orglett.5b02518

  日期：2015.11.6

  A highly efficient, selective synthesis of benzyl esters by palladium catalysis is developed through the bidentate directing group assisted functionalization of multiple C(sp3)–H bonds.

  通过双齿指导基团辅助多个C（sp 3）-H键的官能化，开发了一种高效，选择性地通过钯催化合成苄基酯的方法。
• Palladium catalyzed acetoxylation of benzylic C–H bonds using a bidentate picolinamide directing group
  作者：Tao Cheng、Weiyu Yin、Yi Zhang、Yingnan Zhang、Yong Huang

  DOI：10.1039/c3ob42196a

  日期：——

  A general palladium catalyzed acetoxylation of benzylic C–H bonds has been developed. Picolinamides serve as an excellent directing group for the C–H activation of benzylic methyls. A wide range of 2-amino benzyl alcohol analogues were synthesized in good yields. The products demonstrated broad synthetic utilities toward various benzo-fused heterocycles. Mechanistic studies revealed the key rate-limiting

  已经开发出了一般的钯催化的苄基CH键的乙酰氧基化反应。吡啶甲酰胺是苄基甲基C–H活化的极好指导基团。以高产率合成了多种2-氨基苄醇类似物。该产品对各种苯并稠合杂环具有广泛的合成用途。机理研究表明，关键的限速C–H插入步骤可能受母体芳烃取代模式的影响。
• Palladium-Catalyzed Oxidative Acetoxylation of Benzylic C–H Bond Using Bidentate Auxiliary
  作者：Long Ju、Jinzhong Yao、Zaihong Wu、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1021/jo401830k

  日期：2013.11.1

  Pd(OAc)(2)-catalyzed oxidative acetoxylation of benzylic C-H bonds utilizing a bidentate system has been explored. A variety of picolinoyl- or quinoline-2-carbonyl-protected toluidine derivatives react with PhI(OAc)(2) in the presence of Pd(OAc)(2) to afford the acetoxylated products in synthetically useful yields. A broad of functionalities, such as CH3, F, Cl, Br, I, COCH3, CO2Et, SO2CH3, and NO2, were tolerated. This transformation provides easy access to 2-hydroxymethylaniline derivatives.
• Pd-Catalyzed Arylation/Oxidation of Benzylic C–H Bond
  作者：Yongju Xie、Yuzhu Yang、Lehao Huang、Xunbin Zhang、Yuhong Zhang

  DOI：10.1021/ol300037p

  日期：2012.3.2

  A palladium-catalyzed benzylic C-H arylation/oxidation reaction leading to diaryl ketones has been accomplished. The indispensable role of the bidentate system is disclosed for this sequential process. This chemistry offers a direct new access to a range of diarylketones.
• Palladium-Catalyzed Regioselective Insertion of Carbenes into γ-C(sp³)–H Bonds of Aliphatic Amines
  作者：Peng Zhang、Cheng-xin Li、ShihaoZhi Wang、Xue-jing Zhang、Ming Yan

  DOI：10.1021/acs.orglett.4c00038

  日期：2024.4.5

  migratory insertion of carbenes into distal γ-C(sp3)–H bonds of aliphatic amines has been successfully developed. The synergistic interplay among a palladium catalyst, picolinamide directing group, a carefully selected base additive, and an essential ligand proved crucial in achieving high yields. These findings hold significant value for advancing the exploration of regioselective carbene insertions into

  已成功开发出卡宾迁移插入脂肪胺远端 γ-C(sp 3 )–H 键的方法。钯催化剂、吡啶酰胺导向基团、精心选择的基础添加剂和重要配体之间的协同相互作用被证明对于实现高产率至关重要。这些发现对于推进区域选择性卡宾插入非活化 C(sp 3 )–H 键的探索具有重要价值。