2-(5-fluoro-2-methylphenyl)pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(5-fluoro-2-methylphenyl)pyridine
• 化学式: C₁₂H₁₀FN
• mdl: MFCD07775655
• 分子量: 187.217
• InChiKey: OHVQXTCDMXDBNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 吡啶 、 sodium tetrahydroborate 、 1,10-菲罗啉 、 nickel diacetate 作用下， 生成 2-(5-fluoro-2-methylphenyl)pyridine
  参考文献：
  名称：

  A Micellar Catalysis Strategy for Suzuki–Miyaura Cross-Couplings of 2-Pyridyl MIDA Boronates: No Copper, in Water, Very Mild Conditions

  摘要：

  Suzuki-Miyaura (SM) cross-couplings of 2-pyridyl MIDA boronates can be successfully carried out in the complete absence of copper by attenuation of the Lewis basicity associated with the pyridyl nitrogen using selected substituents (e.g., fluorine or chlorine) on the ring. This strategy imparts additional synthetic options compared with existing approaches based on the use of Lewis acids or N-oxides. Thus, access to highly valued 2-substituted pyridyl rings via an initial Suzuki-Miyaura coupling can be followed by dehalogenation, SNAr reactions, or a second SM coupling to arrive at 2,6-disubstituted pyridyl arrays, all run in a single pot, enabled by micellar catalysis in water. Accessing targets within drug-like space is demonstrated in a four-step, one-pot sequence. Computational data suggest that the major role being played by electron-withdrawing substituents in promoting these cross-couplings without the need for copper is to slow the rates of protodeboronation of intermediate 2-pyridylboronic acids.

  DOI：

  10.1021/acscatal.7b03241

文献信息

• Transition-Metal-Free Decarboxylative Arylation of 2-Picolinic Acids with Arenes under Air Conditions
  作者：Xitao Zhang、Xiujuan Feng、Chuancheng Zhou、Xiaoqiang Yu、Yoshinori Yamamoto、Ming Bao

  DOI：10.1021/acs.orglett.8b03043

  日期：2018.11.16

  transition-metal-free, and direct decarboxylative arylation of 2-picolinic acids with simple arenes is described. The oxidative decarboxylative arylation of 2-picolinic acids with arenes proceeds readily via N-chloro carbene intermediates to afford 2-arylpyridines in satisfactory to good yields under transition-metal-free conditions. This new type of decarboxylative arylation is operationally simple

  描述了2-吡啶甲酸的简单，无过渡金属和直接脱羧芳基化与简单的芳烃。2-吡啶甲酸与芳烃的氧化脱羧芳基化很容易通过N-氯卡宾中间体在无过渡金属条件下以令人满意的产率以令人满意的产率得到2-芳基吡啶。这种新型的脱羧芳基化操作简单且可扩展，并且具有很高的官能团耐受性。在2-吡啶甲酸的脱羧芳基化过程中，各种合成上有用的官能团（例如卤原子，甲氧羰基和硝基）保持完整。
• Rhodium‐Catalyzed C−H Methylation and Alkylation Reactions by Carbene‐Transfer Reactions
  作者：Claire Empel、Sripati Jana、Tim Langletz、Rene M. Koenigs

  DOI：10.1002/chem.202104321

  日期：2022.2.24

  diazoalkanes and their compatibility in this C-H functionalization reaction. With these findings, suitable reaction conditions for the C-H methylation reactions were quickly identified by using highly reactive TMS diazomethane and C-H alkylation reactions with donor/acceptor diazoalkanes, which is applied to a broad scope on alkylation reactions of 2-aryl pyridines with TMS diazomethane and donor/acceptor

  在这项计算和实验相结合的研究中，研究了 2-苯基吡啶与重氮烷的 CH 官能化。通过计算方法进行的初步评估可以评估不同的金属催化剂和重氮烷及其在CH官能化反应中的相容性。基于这些发现，通过使用高反应性的TMS重氮甲烷和CH与供体/受体重氮烷的烷基化反应，快速确定了CH甲基化反应的合适反应条件，该反应广泛应用于2-芳基吡啶与TMS重氮甲烷的烷基化反应和供体/受体重氮烷（51 个实例，产率高达 98%）。
• [EN] N-TERMINALLY MODIFIED GLP-1 RECEPTOR MODULATORS<br/>[FR] MODULATEURS DES RECEPTEUR GLP-1 A MODIFICATION N-TERMINALE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2006127948A2

  公开（公告）日：2006-11-30

  [EN] The subject matter described herein provides novel human glucagon-like peptide-1 (GLP-1) receptor modulators that have biological activity similar or superior to native GLP-1 peptide and thus are useful for the treatment or prevention of diseases or disorders associated with GLP activity. The described compounds include chemically modified peptides that not only stimulate insulin secretion in type II diabetics, but also produce other beneficial insulinotropic responses. These synthetic peptide GLP-1 receptor modulators exhibit increased stability to proteolytic cleavage making them ideal therapeutic candidates for oral or parenteral administration. The disclosed and claimed peptides show desirable pharmacokinetic properties and desirable potency in efficacy models of diabetes.
  [FR] L'invention concerne de nouveaux modulateurs des récepteurs du peptide 1 de type glucagon (GLP-1) humain présentant une activité biologique similaire ou supérieure à celle du peptide natif GLP-1, ces modulateurs étant utilisés pour traiter ou prévenir les maladies et les troubles associés à l'activité de GLP. Les composés décrits comprennent des peptides chimiquement modifiés qui non seulement stimulent la sécrétion d'insuline chez les diabétiques de type II mais produisent également d'autres réponses insulinotropiques bénéfiques. Ces modulateurs des récepteurs du peptide synthétique GLP-1 possèdent une stabilité accrue par rapport à un clivage protéolytique, ce qui fait d'eux des candidats thérapeutiques idéaux pour une administration orale ou parentérale. Les peptides décrits présentent des propriétés pharmacocinétique et une puissance désirées dans des modèles d'efficacité de diabète.
• A Micellar Catalysis Strategy for Suzuki–Miyaura Cross-Couplings of 2-Pyridyl MIDA Boronates: <i>No Copper</i>, in Water, Very Mild Conditions
  作者：Nicholas A. Isley、Ye Wang、Fabrice Gallou、Sachin Handa、Donald H. Aue、Bruce H. Lipshutz

  DOI：10.1021/acscatal.7b03241

  日期：2017.12.1

  Suzuki-Miyaura (SM) cross-couplings of 2-pyridyl MIDA boronates can be successfully carried out in the complete absence of copper by attenuation of the Lewis basicity associated with the pyridyl nitrogen using selected substituents (e.g., fluorine or chlorine) on the ring. This strategy imparts additional synthetic options compared with existing approaches based on the use of Lewis acids or N-oxides. Thus, access to highly valued 2-substituted pyridyl rings via an initial Suzuki-Miyaura coupling can be followed by dehalogenation, SNAr reactions, or a second SM coupling to arrive at 2,6-disubstituted pyridyl arrays, all run in a single pot, enabled by micellar catalysis in water. Accessing targets within drug-like space is demonstrated in a four-step, one-pot sequence. Computational data suggest that the major role being played by electron-withdrawing substituents in promoting these cross-couplings without the need for copper is to slow the rates of protodeboronation of intermediate 2-pyridylboronic acids.