1-(6-Methoxy-2-methylpyridin-3-yl)cyclohex-2-en-1-ol | 156094-75-6

• 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-methylpyridin-3-yl)cyclohex-2-en-1-ol
• CAS: 156094-75-6
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: GKTZTMXNJFEQKJ-UHFFFAOYSA-N

物化性质

• 沸点：
  346.2±42.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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-methylpyridin-3-yl)cyclohex-2-en-1-ol 在 偶氮二异丁腈 、 三正丁基氢锡 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.0h， 生成 2-methoxy-5,6,7,8,8a,9-hexahydroindeno[2,1-b]pyridine-4b-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：

  2-羟基-6-甲基吡啶 在 氢氧化钾 、 正丁基锂 、 四乙基氯化铵 、 溴 、 silver carbonate 、 potassium bromide 作用下， 以 氯仿 为溶剂， 反应 60.42h， 生成 1-(6-Methoxy-2-methylpyridin-3-yl)cyclohex-2-en-1-ol
  参考文献：
  名称：

  Functionalisation of 2-Methoxy-6-methylpyridine

  摘要：

  Selective bromination of 2-methoxy-6-methylpyridine 2 afforded 5-bromo-2-methoxy-6-methylpyridine 8. Deprotonation of this pyridine derivative in benzylic position or lithium-bromine exchange allowed the regio-selective introduction of various electrophiles.

  DOI：

  10.1080/00397919408011740

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.