N-(4-fluoro-2-methylphenyl)picolinamide | 876909-51-2

• 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: N-(4-fluoro-2-methylphenyl)picolinamide
• 英文别名: N-(4-fluoro-2-methylphenyl)pyridine-2-carboxamide
• CAS: 876909-51-2
• 化学式: C₁₃H₁₁FN₂O
• 分子量: 230.242
• InChiKey: MTUXKKCBPIMBMM-UHFFFAOYSA-N

物化性质

• 沸点：
  277.7±35.0 °C(Predicted)
• 密度：
  1.264±0.06 g/cm3(Predicted)

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：

  N-(4-fluoro-2-methylphenyl)picolinamide 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 pyridine-2-carboxylic acid (2-bromomethyl-4-fluoro-phenyl)-amide
  参考文献：
  名称：

  Challenges in the development of mGluR5 positive allosteric modulators: The discovery of CPPHA

  摘要：

  This Letter describes, for the first time, the synthesis and SAR, developed through an iterative analog library approach, that led to the discovery of the positive allosteric modulator (PAM) of the metabotropic glutamate receptor mGluR5 CPPHA. Binding to a unique allosteric binding site distinct from other mGluR5 PAMs, CPPHA has been the focus of numerous pharmacology studies by several laboratories.

  DOI：

  10.1016/j.bmcl.2006.11.081
• 作为产物：
  描述：

  2-吡啶甲酰氯 、 4-氟-2-甲基苯胺 在 N,N-(diisopropyl)aminomethylpolystyrene 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-fluoro-2-methylphenyl)picolinamide
  参考文献：
  名称：

  Challenges in the development of mGluR5 positive allosteric modulators: The discovery of CPPHA

  摘要：

  This Letter describes, for the first time, the synthesis and SAR, developed through an iterative analog library approach, that led to the discovery of the positive allosteric modulator (PAM) of the metabotropic glutamate receptor mGluR5 CPPHA. Binding to a unique allosteric binding site distinct from other mGluR5 PAMs, CPPHA has been the focus of numerous pharmacology studies by several laboratories.

  DOI：

  10.1016/j.bmcl.2006.11.081

文献信息

• 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。
• 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.
• Challenges in the development of mGluR5 positive allosteric modulators: The discovery of CPPHA
  作者：Zhijian Zhao、David D. Wisnoski、Julie A. O’Brien、Wei Lemaire、David L. Williams、Marlene A. Jacobson、Marion Wittman、Sookhee N. Ha、Herve Schaffhauser、Cyrille Sur、Doug J. Pettibone、Mark E. Duggan、P. Jeffrey Conn、George D. Hartman、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2006.11.081

  日期：2007.3

  This Letter describes, for the first time, the synthesis and SAR, developed through an iterative analog library approach, that led to the discovery of the positive allosteric modulator (PAM) of the metabotropic glutamate receptor mGluR5 CPPHA. Binding to a unique allosteric binding site distinct from other mGluR5 PAMs, CPPHA has been the focus of numerous pharmacology studies by several laboratories.