2-溴-4-硝基-6-(2-吡啶基)吡啶1-氧化物 | 205052-97-7

• 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-溴-4-硝基-6-(2-吡啶基)吡啶1-氧化物
• 英文名称: 6-bromo-4-nitro-2,2'-bipyridine 1-oxide
• 英文别名: 6-bromo-4-nitro-2,2'-bipyridine N-oxide；6-Bromo-4-nitro-2,2'-bipyridine-1-oxide；2-bromo-4-nitro-1-oxido-6-pyridin-2-ylpyridin-1-ium
• CAS: 205052-97-7
• 化学式: C₁₀H₆BrN₃O₃
• 分子量: 296.08
• InChiKey: DKAHQFJOSMKPIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-溴-4-硝基-6-(2-吡啶基)吡啶1-氧化物 在 吡啶 、 正丁基锂 、 四甲基乙二胺 、 盐酸羟胺 、 三溴化磷 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 氯仿 为溶剂， 反应 4.5h， 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 、 potassium nitrate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 20.75h， 生成 2-溴-4-硝基-6-(2-吡啶基)吡啶1-氧化物
  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

• An Efficient, Easy Route for the Synthesis of 2,2′:6′,2′′-Terpyridine 1′-Oxides
  作者：Reza-Ali Fallahpour、Markus Neuburger

  DOI：10.1002/1099-0690(200105)2001:10<1853::aid-ejoc1853>3.0.co;2-s

  日期：2001.5

  conditions of the Stille coupling reaction. Derivatives of 2,2′-bipyridine 1-oxides as well as 2,2′:6′,2′′-terpyridine 1′-oxides were synthesised. Oxidation of 2,2′:6′,2′′-terpyridine 1′-oxide with m-CPBA gave 2,2′:6′,2′′-terpyridine 1,1′-dioxide. The crystal structures of 4-nitro-6-bromo-2,2′-bipyridine 1-oxide and 2,2′:6′,2′′-terpyridine 1,1′-dioxide were determined by X-ray structure analysis.

  2,6-二溴吡啶N-氧化物和4-硝基-2,6-二溴吡啶N-氧化物在Stille偶联反应条件下用三丁基(吡啶-2-基)锡烷处理。合成了 2,2'-联吡啶 1-氧化物以及 2,2':6',2''-三联吡啶 1'-氧化物的衍生物。用 m-CPBA 氧化 2,2':6',2''-三联吡啶 1'-氧化物得到 2,2':6',2''-三联吡啶 1,1'-二氧化物。通过X射线结构分析确定了4-硝基-6-溴-2,2'-联吡啶1-氧化物和2,2':6',2''-三联吡啶1,1'-二氧化物的晶体结构。