2,6-dimethoxy-2'-nitrobiphenyl

• 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: 2,6-dimethoxy-2'-nitrobiphenyl
• 英文别名: 2,6-dimethoxy-2'-nitro-1,1'-biphenyl；2-(2,6-dimethoxyphenyl)nitrobenzene；1,3-Dimethoxy-2-(2-nitrophenyl)benzene；1,3-dimethoxy-2-(2-nitrophenyl)benzene
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: PEGCCENDMOKANE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dimethoxy-2'-nitrobiphenyl 在 palladium 10% on activated carbon 、 甲酸铵 、 potassium carbonate 、 potassium iodide 作用下， 以 乙醇 为溶剂， 反应 48.0h， 生成 1-[2-(2,6-dimethoxyphenyl)phenyl]piperazine hydrochloride
  参考文献：
  名称：

  Investigations on the 1-(2-Biphenyl)piperazine Motif: Identification of New Potent and Selective Ligands for the Serotonin₇ (5-HT₇) Receptor with Agonist or Antagonist Action in Vitro or ex Vivo

  摘要：

  Here we report the design, synthesis, and 5-HT7 receptor affinity of a set of 1-(3-biphenyl)- and 1-(2-biphenyl)piperazines. The effect on 5-HT7 affinity of various substituents on the second (distal) phenyl ring was analyzed. Several compounds showed 5-HT7 affinities in the nanomolar range and >100-fold selectivity over 5-HT1A and adrenergic alpha(1) receptors. 1-[2-(4-Methoxyphenyl)phenyl]piperazine (9a) showed 5-HT7 agonist properties in a guinea pig ileum assay but blocked 5-HT-mediated cAMP accumulation in 5-HT(7)(-)expressing HeLa cells.

  DOI：

  10.1021/jm3003679
• 作为产物：
  描述：

  邻硝基苯甲酸 、 2,6-二甲氧基苯甲酸 在 三苯基膦 、 silver carbonate 、 palladium dichloride 作用下， 以 二甲基亚砜 为溶剂， 反应 6.0h， 以70%的产率得到2,6-dimethoxy-2'-nitrobiphenyl
  参考文献：
  名称：

  通过取代苯甲酸的 Pd 催化脱羧均偶联和杂偶联合成联芳基化合物

  摘要：

  通过仔细选择正确的底物比例、催化剂组合和碱，可以通过 Pd 催化的取代苯甲酸的脱羧均偶合和杂偶合轻松合成对称和不对称联芳基化合物。该反应以 40-90% 的产率得到所需产物，并且与 2-硝基-、2-甲氧基-、2-氟-和 2-氯-取代的苯甲酸相容。

  DOI：

  10.1002/ejoc.201100913

文献信息

• Synthesis of Biaryls via Decarboxylative Pd-Catalyzed Cross-Coupling Reaction
  作者：Jean-Michel Becht、Cédric Catala、Claude Le Drian、Alain Wagner

  DOI：10.1021/ol070495y

  日期：2007.4.1

  and efficient route to biaryls via Pd-catalyzed decarboxylative cross-couplings of arene carboxylic acids and aryl iodides is reported. The PdCl2/AsPh3 catalytic system in the presence of Ag2CO3 in DMSO was found to be particularly efficient to perform this transformation. This reaction can be extended to the synthesis of various biaryls, including sterically hindered biaryls, with yields ranging from

  [反应：见正文]据报道，通过芳烃羧酸和芳基碘化物的Pd催化脱羧交叉偶联，可以简单有效地制得联芳基。发现在DMSO中存在Ag2CO3的情况下，PdCl2 / AsPh3催化体系特别有效。该反应可以扩展到包括空间位阻联芳基的各种联芳基的合成，产率为58％至90％。
• The Effect of Intramolecular Hydrogen Bonds on the Rotational Barriers of the Biaryl C−C Axis
  作者：Zheng Dong、Xiaoqiang Ma、Yueyang Yu、Xubin Gu、Depeng Zhao

  DOI：10.1002/chem.202302292

  日期：2023.11.8

  Here, we show that the transition state of atropisomerization of tri-ortho-substituted biaryl was stabilized by intramolecular hydrogen bonds, resulting in a significant reduction in the steric repulsion around C−C axes and a decrease in the energy barrier of atropisomerization (ΔΔG≠(10-9)=46.7 kJ/mol).

  在这里，我们发现三邻位取代的联芳基的阻转异构化过渡态通过分子内氢键稳定，导致C−C轴周围的空间排斥力显着降低，阻转异构化的能垒降低（ΔΔG ≠ ( 10-9 ) = 46.7kJ / mol)。
• Investigations on the 1-(2-Biphenyl)piperazine Motif: Identification of New Potent and Selective Ligands for the Serotonin₇ (5-HT₇) Receptor with Agonist or Antagonist Action in Vitro or ex Vivo
  作者：Enza Lacivita、Daniela Patarnello、Nikolas Stroth、Antonia Caroli、Mauro Niso、Marialessandra Contino、Paola De Giorgio、Pantaleo Di Pilato、Nicola A. Colabufo、Francesco Berardi、Roberto Perrone、Per Svenningsson、Peter B. Hedlund、Marcello Leopoldo

  DOI：10.1021/jm3003679

  日期：2012.7.26

  Here we report the design, synthesis, and 5-HT7 receptor affinity of a set of 1-(3-biphenyl)- and 1-(2-biphenyl)piperazines. The effect on 5-HT7 affinity of various substituents on the second (distal) phenyl ring was analyzed. Several compounds showed 5-HT7 affinities in the nanomolar range and >100-fold selectivity over 5-HT1A and adrenergic alpha(1) receptors. 1-[2-(4-Methoxyphenyl)phenyl]piperazine (9a) showed 5-HT7 agonist properties in a guinea pig ileum assay but blocked 5-HT-mediated cAMP accumulation in 5-HT(7)(-)expressing HeLa cells.
• Synthesis of Biaryls by Pd-Catalyzed Decarboxylative Homo- and Heterocoupling of Substituted Benzoic Acids
  作者：Kai Xie、Sizhuo Wang、Zhiyong Yang、Jidan Liu、Anwei Wang、Xiujian Li、Ze Tan、Can-Cheng Guo、Wei Deng

  DOI：10.1002/ejoc.201100913

  日期：2011.10

  base, symmetrical and unsymmetrical biaryls can be readily synthesized through the Pd-catalyzed decarboxylative homo- and heterocoupling of substituted benzoic acids. The reaction gave the desired products in 40–90 % yield and is compatible with 2-nitro-, 2-methoxy-, 2-fluoro-, and 2-chloro-substituted benzoic acids.

  通过仔细选择正确的底物比例、催化剂组合和碱，可以通过 Pd 催化的取代苯甲酸的脱羧均偶合和杂偶合轻松合成对称和不对称联芳基化合物。该反应以 40-90% 的产率得到所需产物，并且与 2-硝基-、2-甲氧基-、2-氟-和 2-氯-取代的苯甲酸相容。