6-碘-4-甲氧基-2,2'-联吡啶 | 205052-94-4

• 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-碘-4-甲氧基-2,2'-联吡啶
• 英文名称: 6-iodo-4-methoxy-2,2'-bipyridine
• 英文别名: 2-iodo-4-methoxy-6-pyridin-2-ylpyridine
• CAS: 205052-94-4
• 化学式: C₁₁H₉IN₂O
• 分子量: 312.11
• InChiKey: SBTZWWMXVLIIQU-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  404.9±45.0 °C(Predicted)
• 密度：
  1.666±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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-碘-4-甲氧基-2,2'-联吡啶 在 正丁基锂 、 四甲基乙二胺 、 diclazuril 、 重水 作用下， 以 乙醚 、 正己烷 、 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到6-deuterio-4-methoxy-2,2'-bipyridine
  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 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 三溴化磷 、 potassium nitrate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 6.25h， 生成 6-碘-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