4-(6-methoxy-2-methylpyridin-3-yl)octa-1,7-dien-4-ol | 875758-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(6-methoxy-2-methylpyridin-3-yl)octa-1,7-dien-4-ol
• 英文别名: 4-(6-Methoxy-2-methylpyridin-3-yl)octa-1,7-dien-4-ol
• CAS: 875758-00-2
• 化学式: C₁₅H₂₁NO₂
• 分子量: 247.337
• InChiKey: DRHNDOUUEQRFQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-(6-methoxy-2-methylpyridin-3-yl)octa-1,7-dien-4-ol 在 Grubbs catalyst first generation N,N-二甲基丙烯基脲 、 叔丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(6-methoxy-2-(phenylselenylmethyl)pyridin-3-yl)cyclohex-3-en-1-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
• 作为产物：
  描述：

  6-甲氧基-2-甲基-(9CI)-3-吡啶羧醛 在 吡啶 、 戴斯-马丁氧化剂 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-(6-methoxy-2-methylpyridin-3-yl)octa-1,7-dien-4-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

文献信息

• Synthesis of the Bicyclo[3.3.1]nonane Core of Huperzine A and Novel Pyridine-Fused Tricycles by Cyclisation of Pyridine-Based Radicals
  作者：Vittorio Caprio、Jarrod Ward

  DOI：10.3987/com-08-s(d)48

  日期：——

  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.