2-(3,5-dimethylbenzyl)-3-methylpyridine 1-oxide | 1151985-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3,5-dimethylbenzyl)-3-methylpyridine 1-oxide
• 英文别名: 2-[(3,5-Dimethylphenyl)methyl]-3-methyl-1-oxidopyridin-1-ium；2-[(3,5-dimethylphenyl)methyl]-3-methyl-1-oxidopyridin-1-ium
• CAS: 1151985-86-2
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: AYWOALJYODVCNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2,3-二甲基吡啶-N-氧化物 、 3,5-二甲基溴苯 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以90%的产率得到2-(3,5-dimethylbenzyl)-3-methylpyridine 1-oxide
  参考文献：
  名称：

  Catalyst and base controlled site-selective sp2 and sp3 direct arylation of azine N-oxides

  摘要：

  Site-selective direct arylation of both sp(2) and sp(3) sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner The sp arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and. rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement of the base in the mechanism of these reactions. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2008.12.004

文献信息

• Catalyst and base controlled site-selective sp2 and sp3 direct arylation of azine N-oxides
  作者：Derek J. Schipper、Louis-Charles Campeau、Keith Fagnou

  DOI：10.1016/j.tet.2008.12.004

  日期：2009.4

  Site-selective direct arylation of both sp(2) and sp(3) sites on azine N-oxide substrates is described. The arylation reactions are carried out in either a divergent manner or a sequential manner The sp arylation reaction is applied to the synthesis of the natural products, papaverine and crykonisine, and. rationale for low reactivity of electron-deficient aryl halides is provided. Mechanistic investigations point toward the intimate involvement of the base in the mechanism of these reactions. (C) 2008 Published by Elsevier Ltd.