2-n-butyl-1,1,3,3-tetramethyl-4-hydroxypiperidinium iodide | 140176-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2-n-butyl-1,1,3,3-tetramethyl-4-hydroxypiperidinium iodide
• CAS: 140176-35-8
• 化学式: C₁₃H₂₈NO*I
• 分子量: 341.276
• InChiKey: RQGXCGLJJHLNID-FXMYHANSSA-M

反应信息

• 作为产物：
  描述：

  2-n-butyl-1,3,3-trimethyl-4-piperidinol 、 碘甲烷 以 乙醚 为溶剂， 反应 24.0h， 生成 2-n-butyl-1,1,3,3-tetramethyl-4-hydroxypiperidinium iodide
  参考文献：
  名称：

  Synthesis of inhibitors of 2,3-oxidosqualene-lanosterol cyclase: conjugate addition of organocuprates to N-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone.

  摘要：

  Synthesis of ammonium ion analogues of the first cationic intermediate, 5, presumed to be formed during the cyclization of 2,3-oxidosqualene by 2,3-oxidosqualene-lanosterol cyclase are reported. The required 2,3-substituted-4-piperidinols are prepared by conjugate addition of higher order alkyl (2-thienyl)(cyano)cuprates to 1-(carbobenzyloxy)-3-carbomethoxy-5,6-dihydro-4-pyridone. The nitrogen protecting group (carbobenzyloxy) is key to the synthesis in that it allows the conjugate addition to proceed in high yield and is easily converted to the required N-methyl group in the final products. The key terpenoid side chain appended to C-2 of the piperidinols was constructed from homofarnesyl bromide and 1,5-difunctionalized homoisopentenyl derivatives prepared by zirconium-catalyzed carboalumination of protected 1-butyn-4-ol.

  DOI：

  10.1021/jo00036a008