2-bromo-6-phenylpyridine 1-oxide | 1097732-14-3

• 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
• 英文名称: 2-bromo-6-phenylpyridine 1-oxide
• 英文别名: 2-Bromo-6-phenylpyridine N-oxide；2-bromo-1-oxido-6-phenylpyridin-1-ium
• CAS: 1097732-14-3
• 化学式: C₁₁H₈BrNO
• 分子量: 250.095
• InChiKey: UQOUFKLOWWWXSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 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：
  25.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-苯基吡啶1-氧化物 在 四溴化碳 、 lithium tert-butoxide 作用下， 以 N,N-二甲基甲酰胺 、 间二甲苯 为溶剂， 反应 1.0h， 以56%的产率得到2-bromo-6-phenylpyridine 1-oxide
  参考文献：
  名称：

  A Simple Base-Mediated Halogenation of Acidic sp² C−H Bonds under Noncryogenic Conditions

  摘要：

  A new method has been developed for in situ halogenation of acidic Sp(2) carbon-hydrogen bonds in heterocycles and electron-deficient arenes. Either selective monohalogenation or one-step exhaustive polyhalogenation is possible for substrates possessing several C-H bonds that are flanked by electron-withdrawing groups. For the most acidic arenes, such as pentafluorobenzene, K3PO4 base can be employed instead of BuLi for metalation/halogenation sequences.

  DOI：

  10.1021/ol802411f

文献信息

• In Situ Generation and Trapping of Aryllithium and Arylpotassium Species by Halogen, Sulfur, and Carbon Electrophiles
  作者：Ilya Popov、Hien-Quang Do、Olafs Daugulis

  DOI：10.1021/jo9015369

  日期：2009.11.6

  A general method has been developed for in situ trapping of arylmetal intermediates by halogen, sulfur, ketone, and aldehyde electrophiles affording the functionalization of the most acidic position in arene Pentafluorobenzene, benzothiazole,and benzoxazole can be functionalized by using K3PO4 base. For less acidic arenes, tBuOLi base is required. Arenes with DMSO pK(a) values of 35 or less are reactive.
• A Simple Base-Mediated Halogenation of Acidic sp² C−H Bonds under Noncryogenic Conditions
  作者：Hien-Quang Do、Olafs Daugulis

  DOI：10.1021/ol802411f

  日期：2009.1.15

  A new method has been developed for in situ halogenation of acidic Sp(2) carbon-hydrogen bonds in heterocycles and electron-deficient arenes. Either selective monohalogenation or one-step exhaustive polyhalogenation is possible for substrates possessing several C-H bonds that are flanked by electron-withdrawing groups. For the most acidic arenes, such as pentafluorobenzene, K3PO4 base can be employed instead of BuLi for metalation/halogenation sequences.