1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)cyclohex-2-en-ol | 875757-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)cyclohex-2-en-ol
• 英文别名: 1-[6-Methoxy-2-(phenylselanylmethyl)pyridin-3-yl]cyclohex-2-en-1-ol
• CAS: 875757-95-2
• 化学式: C₁₉H₂₁NO₂Se
• 分子量: 374.341
• InChiKey: JRKHKSAYXDJVJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)cyclohex-2-en-ol 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97%的产率得到2-methoxy-5,6,7,8,8a,9-hexahydroindeno[2,1-b]pyridine-4b-ol
  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：

  2-甲氧基-5-溴-6-甲基吡啶 在 正丁基锂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)cyclohex-2-en-ol
  参考文献：
  名称：

  A radical mediated approach to the core structure of huperzine A

  摘要：

  The synthesis of the core structure of huperzine A by cyclisation of 2-pyridylmethyl radicals is described. (2-Methylpyridin-3-yl)cyclohexenols are directly selenated at the benzylic position by deprotonation/selenation and the products undergo either 5-exo-trig or 6-exo-trig radical cyclisations giving access to hexahydroindenopyridines and the bicyclo[3.3.1]nonane core of huperzine A, respectively. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.037