4-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-2,6-dichloro-3-methyl-pyridine | 138944-47-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-2,6-dichloro-3-methyl-pyridine
• CAS: 138944-47-5
• 化学式: C₁₆H₂₇Cl₂NOSi
• 分子量: 348.388
• InChiKey: YWNPQFOXTCUQJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  396.1±42.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  22.12
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 、 3,5-二氯-6-甲基-1,4-噁唑-2-酮 反应 20.0h， 以17%的产率得到4-[4-(tert-Butyl-dimethyl-silanyloxy)-butyl]-2,6-dichloro-3-methyl-pyridine
  参考文献：
  名称：

  An approach to acyclo-1-deazathymidine c-nucleosides via 3,5-dichloro-6-methyl-2H-1,4-oxazin-2-one.

  摘要：

  An approach to the synthesis of acyclo-1-deazathymidine nucleosides is described. Diels-Alder reaction of 3,5-dichloro-6-methyl-2H-1,4-oxazin-2-one with acetylenic compounds 4 and 5 yielded the 3-[(tetrahydropyran-2-yl)oxy]methyl- and 3-bromomethyl-5-methyl-2,6-dichloropyridine intermediates 7 and 8. The bromomethyl group of compound 8 underwent easy substitution with the appropriate nucleophiles, permitting the introduction of acyclo sugar moieties. The resulting 3-substituted 2,6-dichloro-5-methyl pyridines 9a,b - precursors for some acyclo pyridine-C-nucleosides - were treated with sodium phenylmethoxide to afford 2,6-dibenzyloxpyridines 10a,b. Debenzylation using a palladium-strontium carbonate catalyst gave the unstable C-nucelosides 2a,b of the 6-hydroxy-1-H-pyridin-2-one type. A stable 6-hydroxy-1-H-pyridin-2-one 2c, exempt from benzylic oxygen, was obtained via cycloaddition of THP-protected 6-hydroxy-1-hexyne.

  DOI：

  10.1016/s0040-4020(01)96055-7