6-溴-4-甲氧基-2,2'-联吡啶 | 205052-93-3

• 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: 6-溴-4-甲氧基-2,2'-联吡啶
• 英文名称: 6-bromo-4-methoxy-2,2'-bipyridine
• 英文别名: 2-bromo-4-methoxy-6-pyridin-2-ylpyridine
• CAS: 205052-93-3
• 化学式: C₁₁H₉BrN₂O
• 分子量: 265.109
• InChiKey: LCSPTQXSTGZSGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-溴-4-甲氧基-2,2'-联吡啶 在 吡啶 、 正丁基锂 、 四甲基乙二胺 、 盐酸羟胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 为溶剂， 反应 16.25h， 生成 (2E)-4-甲氧基-3-甲硫基-2-(亚硝基亚甲基)-6-(2-吡啶基)-1H-吡啶
  参考文献：
  名称：

  First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A

  摘要：

  Caerulomycins produced by Streptomyces caeruleus, and collismycins more recently isolated from Streptomyces species, are bipyridinic molecules endowed with antibiotic and cytotoxic activities. The first syntheses of caerulomycin E (1), as well as new syntheses of caerulomycin A (2), are reported. Methodologies involving efficiently controlled reactions such as metalation and cross-coupling reactions have been developed from 2,2'-bipyridine. The functionalization at C-6 could be achieved by metalation of 2,2'-bipyridine N-oxides 5 and 12. 6-Halo-4-methoxy-2,2'-bipyridines (6, 10, 11) became key-molecules of these different pathways, and further functionalization at C-5 allowed the first syntheses of collismycins A (3) and C (4).

  DOI：

  10.1021/jo972022i
• 作为产物：
  描述：

  2,2′-二吡啶基 N-氧化物 在 硫酸 、 三溴化磷 、 potassium nitrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 氯仿 为溶剂， 反应 5.0h， 生成 6-溴-4-甲氧基-2,2'-联吡啶
  参考文献：
  名称：

  First Syntheses of Caerulomycin E and Collismycins A and C. A New Synthesis of Caerulomycin A

  摘要：

  Caerulomycins produced by Streptomyces caeruleus, and collismycins more recently isolated from Streptomyces species, are bipyridinic molecules endowed with antibiotic and cytotoxic activities. The first syntheses of caerulomycin E (1), as well as new syntheses of caerulomycin A (2), are reported. Methodologies involving efficiently controlled reactions such as metalation and cross-coupling reactions have been developed from 2,2'-bipyridine. The functionalization at C-6 could be achieved by metalation of 2,2'-bipyridine N-oxides 5 and 12. 6-Halo-4-methoxy-2,2'-bipyridines (6, 10, 11) became key-molecules of these different pathways, and further functionalization at C-5 allowed the first syntheses of collismycins A (3) and C (4).

  DOI：

  10.1021/jo972022i

文献信息

• Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines
  作者：Vincent K. Duong、Alexandra M. Horan、Eoghan M. McGarrigle

  DOI：10.1021/acs.orglett.0c03048

  日期：2020.11.6

  arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl

  开发了具有良好官能团耐受性的吡啶基硫醚的S选择性芳基化反应。为了证明其合成实用性，将所得吡啶基yl盐用于可扩展的无过渡金属偶联方案中，得到具有广泛官能团耐受性的官能化联吡啶。该模块化方法允许从可商购的吡啶基卤中选择性引入官能团，从而提供对称和不对称的2,2'-和2,3'-联吡啶。该方法的迭代应用使得能够合成具有三种不同吡啶组分的官能化的吡啶。
• Synthesis of Bis-heteroaryls Using Grignard Reagents and Pyridylsulfonium Salts
  作者：Alexandra M. Horan、Vincent K. Duong、Eoghan M. McGarrigle

  DOI：10.1021/acs.orglett.1c03379

  日期：2021.12.3

  reported ligand-coupling reactions of Grignard reagents with pyridylsulfonium salts. The method has wide functional group tolerance and enables the formation of bis-heterocycle linkages, including 2,4′-, 2,3′-, and 2,2′-bipyridines, as well as pyridines linked to pyrimidines, pyrazines, isoxazoles, and benzothiophenes. The methodology was successfully applied to the synthesis of the natural products caerulomycin

  本文报道了格氏试剂与吡啶基锍盐的配体偶联反应。该方法具有广泛的官能团耐受性，能够形成双杂环键，包括 2,4'-、2,3'-和 2,2'-联吡啶，以及与嘧啶、吡嗪、异恶唑连接的吡啶，和苯并噻吩。该方法成功地应用于天然产物 caerulomycin A 和 E 的合成。
• USE OF COLLISMYCIN AND DERIVATIVES THEREOF AS OXIDATIVE STRESS INHIBITORS
  申请人：Martinez Gil Ana

  公开号：US20100048635A2

  公开（公告）日：2010-02-25

  The present invention relates to the use of Collismycin and derivatives thereof as inhibitors of oxidative stress in cells and their use for the preparation of medicaments for the treatment and/or prevention of oxidative stress-induced diseases or conditions, especially neurodegenerative diseases, such as Alzheimer's Disease and Parkinson's Disease.

  本发明涉及使用Collismycin及其衍生物作为细胞内氧化应激的抑制剂，以及它们用于制备治疗和/或预防氧化应激引起的疾病或病状的药物，尤其是神经退行性疾病，如阿尔茨海默病和帕金森病。
• Use of Collismycin and Derivatives Thereof as Oxidative Stress Inhibitors
  申请人：Martinez Gil Ana

  公开号：US20080275088A1

  公开（公告）日：2008-11-06

  The present invention relates to the use of Collismycin and derivatives thereof as inhibitors of oxidative stress in cells and their use for the preparation of medicaments for the treatment and/or prevention of oxidative stress-induced diseases or conditions, especially neurodegenerative diseases, such as Alzheimer's Disease and Parkinson's Disease.

  本发明涉及使用Collismycin及其衍生物作为细胞内氧化应激抑制剂及其用于制备治疗和/或预防氧化应激引起的疾病或症状的药物，特别是神经退行性疾病，如阿尔茨海默病和帕金森病。
• Use of collismycin and derivatives thereof as oxidative stress inhibitors
  申请人：Neuropharma S.A.

  公开号：EP1749552A1

  公开（公告）日：2007-02-07

  The present invention relates to the use of Collismycin and derivatives thereof as inhibitors of oxidative stress in cells and their use for the preparation of medicaments for the treatment of oxidative stress-induced diseases or conditions, specially neurodegenerative diseases, such as Alzheimer's Disease and Parkinson's Disease.

  本发明涉及科利霉素及其衍生物作为细胞氧化应激抑制剂的用途，以及它们用于制备治疗氧化应激引起的疾病或病症的药物，特别是神经退行性疾病，如阿尔茨海默氏症和帕金森氏症。