4-(2,6-dichloro-5-methylpyridin-3-yl)butan-1-ol | 138944-45-3

• 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: 4-(2,6-dichloro-5-methylpyridin-3-yl)butan-1-ol
• CAS: 138944-45-3
• 化学式: C₁₀H₁₃Cl₂NO
• 分子量: 234.125
• InChiKey: DLLUHNIAQJWYFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.12
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(2,6-dichloro-5-methylpyridin-3-yl)butan-1-ol 在 Dowex 50WX₈(H+) 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 2.0h， 生成 2,6-dibenzyloxy-3-(4-hydroxybutyl)-5-methylpyridine
  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
• 作为产物：
  描述：

  6-(叔-丁基二甲基硅烷基氧基)-1-己炔 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 生成 4-(2,6-dichloro-5-methylpyridin-3-yl)butan-1-ol
  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

文献信息

• An approach to acyclo-1-deazathymidine c-nucleosides via 3,5-dichloro-6-methyl-2H-1,4-oxazin-2-one.
  作者：Lieven Meerpoel、Suzanne M. Toppet、Frans Compernolle、Georges J. Hoornaert

  DOI：10.1016/s0040-4020(01)96055-7

  日期：1991.1

  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.