[(6-methoxypyridin-3-yl)methyl]dimethylamine | 162475-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(6-methoxypyridin-3-yl)methyl]dimethylamine
• 英文别名: 1-(6-methoxypyridin-3-yl)-N,N-dimethylmethanamine
• CAS: 162475-78-7
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: CZKXHBGVGPQOCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  25.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(6-methoxypyridin-3-yl)methyl]dimethylamine 在 三甲基氯硅烷 、 sodium iodide 作用下， 以 乙腈 为溶剂， 以68%的产率得到5-[(dimethylamino)methyl]-3H-pyridin-2-one
  参考文献：
  名称：

  Synthesis of huperzine A, its analogs, and their anticholinesterase activity

  摘要：

  Huperzine A is a new alkaloid isolated from the club moss Huperzia serrata (Thunb.) Trev., a Chinese folk medicine. This alkaloid exhibits potent activity as an inhibitor of acetylcholinesterase. Consequently, the compound is presently being investigated in China for the treatment of individuals suffering from various forms of memory impairment including Alzheimer's dementia. Details of the total synthesis of (+/-)-huperzine A are described as well as the preparation of a variety of huperzine analogues including its presumed pharmacophore. The extent of these new compounds to inhibit acetylcholinesterase is presented along with a discussion of the effects of the structural changes on biological activity.

  DOI：

  10.1021/jo00015a014
• 作为产物：
  描述：

  2-甲氧基吡啶 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 20.75h， 生成 [(6-methoxypyridin-3-yl)methyl]dimethylamine
  参考文献：
  名称：

  二丁基（异丙基）镁酸锂（1-）和氯化锂通过卤素-镁交换进行非低温合成功能化的2-甲氧基吡啶

  摘要：

  使用二丁基（异丙基）镁酸锂（1-）和相应的溴或碘类似物制备在3-，5-或6-位官能化的2-甲氧基吡啶和在3-位官能化的2,6-二甲氧基吡啶。非低温条件下的氯化锂。根据在两种镁酸盐之间的选择以及反应介质中氯化锂的存在与否，对程序进行了优化。 吡啶-镁-锂-有机金属试剂

  DOI：

  10.1055/s-0031-1289687

文献信息

• Efficient Synthesis of 5-Functionalised 2-Methoxypyridines and their Transformation to Bicyclic δ-Lactams, both Accessed Using Magnesium ‘Ate’ Complexes as Key Reagents
  作者：Jacek Sośnicki

  DOI：10.1055/s-0029-1217733

  日期：2009.9

  Simple and efficient synthesis of 5-functionalised ­2-methoxypyridines from 5-bromo-2-methoxypyridine using ­[n-Bu3Mg]Li performed in noncryogenic conditions is described. Application of 5-functionalised 2-methoxypyridines in the synthesis of 1-substituted 3,6,9,9a-tetrahydroquinolizin-4-ones and 3,5,8,8a-tetrahydro-1H-quinolin-2-ones via allylation of the corresponding 5-functionalised N-allyl(or benzyl)pyridin-2-ones using ­[allyln-Bu2Mg]Li followed by ring-closing metathesis is presented.

  介绍了在非致冷条件下使用[n-Bu3Mg]Li 从 5-溴-2-甲氧基吡啶简单而高效地合成 5-官能化 2-甲氧基吡啶的过程。介绍了使用[烯丙基-Bu2Mg]Li 通过烯丙基化相应的 5-官能化 N-烯丙基（或苄基）吡啶-2-酮，然后进行闭环偏析，将 5-官能化 2-甲氧基吡啶应用于合成 1-取代的 3,6,9,9a-四氢喹嗪-4-酮和 3,5,8,8a-四氢-1H-喹啉-2-酮。
• Noncryogenic Synthesis of Functionalized 2-Methoxypyridines by Halogen-Magnesium Exchange Using Lithium Dibutyl(isopropyl)magnesate(1-) and Lithium Chloride
  作者：Jacek Sośnicki、Łukasz Struk

  DOI：10.1055/s-0031-1289687

  日期：2012.3

  corresponding bromo or iodo analogues by using lithium dibutyl(isopropyl)magnesate(1-) and lithium chloride under noncryogenic conditions. The procedure was optimized in terms of the choice between two magnesates and the presence or absence of lithium chloride in the reaction medium. pyridines - magnesium - lithium - organometallic reagents

  使用二丁基（异丙基）镁酸锂（1-）和相应的溴或碘类似物制备在3-，5-或6-位官能化的2-甲氧基吡啶和在3-位官能化的2,6-二甲氧基吡啶。非低温条件下的氯化锂。根据在两种镁酸盐之间的选择以及反应介质中氯化锂的存在与否，对程序进行了优化。 吡啶-镁-锂-有机金属试剂
• Synthesis of huperzine A, its analogs, and their anticholinesterase activity
  作者：Alan P. Kozikowski、Yan Xia、E. Rajarathnam Reddy、Werner Tuckmantel、Israel Hanin、X. C. Tang

  DOI：10.1021/jo00015a014

  日期：1991.7

  Huperzine A is a new alkaloid isolated from the club moss Huperzia serrata (Thunb.) Trev., a Chinese folk medicine. This alkaloid exhibits potent activity as an inhibitor of acetylcholinesterase. Consequently, the compound is presently being investigated in China for the treatment of individuals suffering from various forms of memory impairment including Alzheimer's dementia. Details of the total synthesis of (+/-)-huperzine A are described as well as the preparation of a variety of huperzine analogues including its presumed pharmacophore. The extent of these new compounds to inhibit acetylcholinesterase is presented along with a discussion of the effects of the structural changes on biological activity.