5,5'-dibromo-2'-chloro-3,4-dihydro-1H-[4,4']bipyridinyl-2-one | 1227402-58-5

• 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: 5,5'-dibromo-2'-chloro-3,4-dihydro-1H-[4,4']bipyridinyl-2-one
• 英文别名: 5-bromo-4-(5-bromo-2-chloropyridin-4-yl)-3,4-dihydro-1H-pyridin-2-one
• CAS: 1227402-58-5
• 化学式: C₁₀H₇Br₂ClN₂O
• 分子量: 366.439
• InChiKey: FEYLACBXUVKAJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴-2-氯吡啶 在 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以8%的产率得到2,2'-dichloro-5,5'dibromo-4,4'-bipyridine
  参考文献：
  名称：

  Synthesis of Polyhalogenated 4,4′-Bipyridines via a Simple Dimerization Procedure

  摘要：

  Polyhalogenated 4,4'-bipyridines were conveniently synthesized in a single step starting from dihalo-pyridines. A mechanism was proposed on the basis of experiments performed with 2-chloro-5-bromopyridine I a. 2-Chloro-4-lithio-5-bromopyridine A1 was produced via ortholithiation of la by using either LDA or t-BuLi bases. When LDA was used, chiller 3a containing two chlorines and two bromine atoms was formed predominantly accompanied by several byproducts whose structure and mechanism of formation are discussed. In the case of t-BuLi, although the major product was 2-chloropyridine 7, a new pyridone product 8 was formed that is probably the result of the dihydropyridine intermediate hydrolysis. The dimerization procedure involving LDA was employed to prepare a large number of halogenated 4,4'-bipyridines in moderate to good yields. In some specific cases, halogenated 3,4' and 2,4'-bipyridines were obtained in lower yields and their structures were unambiguously assigned by X-ray diffraction analysis.

  DOI：

  10.1021/jo100152e

文献信息

• Synthesis of Polyhalogenated 4,4′-Bipyridines via a Simple Dimerization Procedure
  作者：Mohamed Abboud、Victor Mamane、Emmanuel Aubert、Claude Lecomte、Yves Fort

  DOI：10.1021/jo100152e

  日期：2010.5.21

  Polyhalogenated 4,4'-bipyridines were conveniently synthesized in a single step starting from dihalo-pyridines. A mechanism was proposed on the basis of experiments performed with 2-chloro-5-bromopyridine I a. 2-Chloro-4-lithio-5-bromopyridine A1 was produced via ortholithiation of la by using either LDA or t-BuLi bases. When LDA was used, chiller 3a containing two chlorines and two bromine atoms was formed predominantly accompanied by several byproducts whose structure and mechanism of formation are discussed. In the case of t-BuLi, although the major product was 2-chloropyridine 7, a new pyridone product 8 was formed that is probably the result of the dihydropyridine intermediate hydrolysis. The dimerization procedure involving LDA was employed to prepare a large number of halogenated 4,4'-bipyridines in moderate to good yields. In some specific cases, halogenated 3,4' and 2,4'-bipyridines were obtained in lower yields and their structures were unambiguously assigned by X-ray diffraction analysis.