2-甲氧基-5-(吡啶-4-基)苯硼酸 | 196861-33-3

• 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
• 中文名称: 2-甲氧基-5-(吡啶-4-基)苯硼酸
• 英文名称: 2-methoxy-5-(4-pyridinyl)phenylboronic acid
• 英文别名: (2-Methoxy-5-(pyridin-4-yl)phenyl)boronic acid；(2-methoxy-5-pyridin-4-ylphenyl)boronic acid
• CAS: 196861-33-3
• 化学式: C₁₂H₁₂BNO₃
• mdl: MFCD06658467
• 分子量: 229.043
• InChiKey: QLNYKODXAPVKKX-UHFFFAOYSA-N

物化性质

• 沸点：
  462.4±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.76
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  62.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴吡啶 、 2-甲氧基-5-(吡啶-4-基)苯硼酸 在 chromium dichloride 、 四(三苯基膦)钯 、 sodium carbonate 、 cesium fluoride 、 4,4'-二叔丁基-2,2'-二吡啶 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 30.0h， 生成 2-(3-(pyridine-4-yl)phenyl)pyridine
  参考文献：
  名称：

  未活化的芳香族和苄基 C-O 键的铬催化还原裂解

  摘要：

  据报道，铬催化还原性裂解芳香族和苄基 C-O 键。这种脱氧反应由低成本的 CrCl2 预催化剂与作为温和还原剂的聚（甲基氢硅氧烷）结合促进，提供了一种通过裂解未活化的 C-O 键形成还原基序的策略。一系列的官能团如溴、氯、氟、羟基、氨基和烷氧基羰基可以保留在还原过程中。

  DOI：

  10.1055/a-1507-6419
• 作为产物：
  描述：

  4-氯吡啶 在 正丁基锂 、 溴 、 碘 、 magnesium 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 79.5h， 生成 2-甲氧基-5-(吡啶-4-基)苯硼酸
  参考文献：
  名称：

  Large-Scale Negishi Coupling as Applied to the Synthesis of PDE472, an Inhibitor of Phosphodiesterase Type 4D

  摘要：

  5-[2-Methoxy-5-(4-pyridinyl)phenyl]-2,1,3-benzoxadiazole (PDE472) is a selective inhibitor of the phosphodiesterase PDE4D isoenzyme, which is a recognised drug target for the treatment of asthma. Different synthetic routes to PDE472 were investigated, and the research synthesis was optimised to prepare a phase I batch on pilot-plant scale with the focus on the elimination or minimization of inherent process risks. An important refinement of the key Negishi aryl-aryl coupling involved preforming the arylpalladium complex, which was then added to the arylzinc intermediate. Residual palladium was removed from PDE472 via crystallization of the hemi-maleate salt, which afforded drug-substance containing < 2 ppm Pd.

  DOI：

  10.1021/op025615q

文献信息

• Phenylpyridine derivatives useful as phosphodiesterase inhibitors
  申请人：——

  公开号：US20020028831A1

  公开（公告）日：2002-03-07

  (4-oxy-3-(aryl)phenyl)pyridine compounds, in free or acid addition salt form, are useful as pharmaceuticals for treatment and prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. for asthma therapy. Preferred compounds are novel biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds. The compounds are selective inhibitors of PDE 4 isoenzyme activity and also act to down regulate or inhibit TNF-&agr; release.

  (4-氧代-3-(芳基)苯基)吡啶化合物，以自由形式或酸盐形式，作为药物用于治疗和预防炎症，特别是空气道的炎症或阻塞性疾病，例如哮喘治疗。优选的化合物是新型的联苯基吡啶、联苯基苯甲酰胺和联苯基苯基羧酸化合物。这些化合物是PDE 4同工酶活性的选择性抑制剂，同时也可以下调或抑制TNF-α的释放。
• 4-oxy-3-(aryl)phenyl-arylcarbonyloxy compounds useful as phosphodiesterase inhibitors
  申请人：Novartis AG

  公开号：US06258843B1

  公开（公告）日：2001-07-10

  (4-oxy-3-(aryl)phenyl)pyridine compounds, in free or acid addition salt form, are useful as pharmaceuticals for treatment and prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. for asthma therapy. Preferred compounds are novel biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds. The compounds are selective inhibitors of PDE 4 isoenzyme activity and also act to down regulate or inhibit TNF-&agr; release.

  (4-氧代-3-(芳基)苯基)吡啶化合物，以自由形式或酸加成盐形式，可用作药物治疗和预防炎症，特别是气道炎症或阻塞性疾病，例如哮喘治疗。首选化合物是新型联苯基吡啶、联苯基苯甲酰胺和联苯基苯基羧酸化合物。这些化合物是PDE 4同工酶活性的选择性抑制剂，同时也具有下调或抑制TNF-α释放的作用。
• Triaryl compounds
  申请人：Novartis AG

  公开号：US06288092B1

  公开（公告）日：2001-09-11

  (4-oxy-3-(aryl)phenyl)pyridine compounds, in free or acid addition salt form, are useful as pharmaceuticals for treatment and prophylaxis of inflammation, particularly inflammatory or obstructive diseases of the airways, e.g. for asthma therapy. Preferred compounds are novel biphenyl pyridines, biphenyl benzamides and biphenyl phenylcarboxy compounds. The compounds are selective inhibitors of PDE 4 isoenzyme activity and also act to down regulate or inhibit TNF-&agr; release.

  (4-氧代-3-(芳基)苯基)吡啶类化合物，以自由或酸盐形式，可用作药物治疗和预防炎症，特别是呼吸道的炎症或阻塞性疾病，例如哮喘治疗。优选的化合物是新型联苯基吡啶、联苯基苯甲酰胺和联苯基苯甲酸类化合物。这些化合物是PDE 4同工酶活性的选择性抑制剂，同时也具有下调或抑制TNF-α释放的作用。
• Chromium-Catalyzed Reductive Cleavage of Unactivated Aromatic and Benzylic C–O Bonds
  作者：Meiming Luo、Xiaoming Zeng、Shuqing Yuan、Liang Ling、Jinghua Tang

  DOI：10.1055/a-1507-6419

  日期：2021.9

  Reductive cleavage of aromatic and benzylic C–O bonds by chromium catalysis is reported. This deoxygenative reaction was promoted by low-cost CrCl2 precatalyst combined with poly(methyl hydrogen siloxane) as the mild reducing agent, providing a strategy in forming reduced motifs by cleavage of unactivated C–O bonds. A range of functional groups such as bromide, chloride, fluoride, hydroxyl, amino,

  据报道，铬催化还原性裂解芳香族和苄基 C-O 键。这种脱氧反应由低成本的 CrCl2 预催化剂与作为温和还原剂的聚（甲基氢硅氧烷）结合促进，提供了一种通过裂解未活化的 C-O 键形成还原基序的策略。一系列的官能团如溴、氯、氟、羟基、氨基和烷氧基羰基可以保留在还原过程中。
• Large-Scale Negishi Coupling as Applied to the Synthesis of PDE472, an Inhibitor of Phosphodiesterase Type 4D
  作者：Paul W. Manley、Murat Acemoglu、Wolfgang Marterer、Werner Pachinger

  DOI：10.1021/op025615q

  日期：2003.5.1

  5-[2-Methoxy-5-(4-pyridinyl)phenyl]-2,1,3-benzoxadiazole (PDE472) is a selective inhibitor of the phosphodiesterase PDE4D isoenzyme, which is a recognised drug target for the treatment of asthma. Different synthetic routes to PDE472 were investigated, and the research synthesis was optimised to prepare a phase I batch on pilot-plant scale with the focus on the elimination or minimization of inherent process risks. An important refinement of the key Negishi aryl-aryl coupling involved preforming the arylpalladium complex, which was then added to the arylzinc intermediate. Residual palladium was removed from PDE472 via crystallization of the hemi-maleate salt, which afforded drug-substance containing < 2 ppm Pd.