1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)-3-(1-(triethylsilyloxy)cyclohex-3-ene) | 1161754-02-4

• 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: 1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)-3-(1-(triethylsilyloxy)cyclohex-3-ene)
• 英文别名: Triethyl-[1-[6-methoxy-2-(phenylselanylmethyl)pyridin-3-yl]cyclohex-3-en-1-yl]oxysilane
• CAS: 1161754-02-4
• 化学式: C₂₅H₃₅NO₂SeSi
• 分子量: 488.604
• InChiKey: WGPLDVZOJHIWJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)-3-(1-(triethylsilyloxy)cyclohex-3-ene) 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 6.5h， 以73%的产率得到1-(triethylsilyloxy)-5-methoxy-6-azatricyclo[7.3.1.0(2,7)]trideca-2,4,6-triene
  参考文献：
  名称：

  Synthesis of the Bicyclo[3.3.1]nonane Core of Huperzine A and Novel Pyridine-Fused Tricycles by Cyclisation of Pyridine-Based Radicals

  摘要：

  The cyclisation of 3-pyridyl radicals and (2-pyridyl)methyl radicals, generated from (pyridyl)cyclohexenols 5 to 8, has been examined as part of a model study directed towards the synthesis of huperzine A. The 3-pyridyl radical, generated from 3-bromopyridine 5, undergoes 5-exo-trig cyclisation to give hexahydroindenopyridine 10. Related pyridine-fused tricycle 12 is formed by 5-exo-trig cyclization of the (2-pyridyl)methyl radical derived from selenide 7b, while the radicals generated from selenides 8b and 19 undergo 6-exo-trig cyclisation to give the bicyclo[3.3.1]nonane core of huperzine A.

  DOI：

  10.3987/com-08-s(d)48
• 作为产物：
  描述：

  1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)cyclohex-3-en-1-ol 、 三乙基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以63%的产率得到1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)-3-(1-(triethylsilyloxy)cyclohex-3-ene)
  参考文献：
  名称：

  Synthesis of the Bicyclo[3.3.1]nonane Core of Huperzine A and Novel Pyridine-Fused Tricycles by Cyclisation of Pyridine-Based Radicals

  摘要：

  The cyclisation of 3-pyridyl radicals and (2-pyridyl)methyl radicals, generated from (pyridyl)cyclohexenols 5 to 8, has been examined as part of a model study directed towards the synthesis of huperzine A. The 3-pyridyl radical, generated from 3-bromopyridine 5, undergoes 5-exo-trig cyclisation to give hexahydroindenopyridine 10. Related pyridine-fused tricycle 12 is formed by 5-exo-trig cyclization of the (2-pyridyl)methyl radical derived from selenide 7b, while the radicals generated from selenides 8b and 19 undergo 6-exo-trig cyclisation to give the bicyclo[3.3.1]nonane core of huperzine A.

  DOI：

  10.3987/com-08-s(d)48