(5S,8R,8aS)-5-(2-chlorophenyl)-8-methyl-6-(3-methylbut-2-enyl)-3,5,6,7,8,8a-hexahydro-2H-pyrano[3,2-c]pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (5S,8R,8aS)-5-(2-chlorophenyl)-8-methyl-6-(3-methylbut-2-enyl)-3,5,6,7,8,8a-hexahydro-2H-pyrano[3,2-c]pyridine
• 英文别名: (5S,8R,8aS)-5-(2-chlorophenyl)-8-methyl-6-(3-methylbut-2-enyl)-2,3,5,7,8,8a-hexahydropyrano[3,2-c]pyridine
• 化学式: C₂₀H₂₆ClNO
• 分子量: 331.886
• InChiKey: ABSLZVHPFVGBIH-YSGRDPCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  三聚甲醛 、 (3E,5E)-4-((2-chlorophenyl)(3-methylbut-2-enylamino)methyl)hepta-3,5-dien-1-ol 在 D(+)-10-樟脑磺酸 、 sodium hydroxide 作用下， 以 乙腈 、 水 为溶剂， 反应 20.0h， 生成 (5S,8R,8aR)-5-(2-chlorophenyl)-8-methyl-6-(3-methylbut-2-enyl)-3,5,6,7,8,8a-hexahydro-2H-pyrano[3,2-c]pyridine 、 (5S,8R,8aS)-5-(2-chlorophenyl)-8-methyl-6-(3-methylbut-2-enyl)-3,5,6,7,8,8a-hexahydro-2H-pyrano[3,2-c]pyridine
  参考文献：
  名称：

  Convergent Synthesis of Piperidines by the Union of Conjugated Alkynes with Imines: A Unique Regioselective Bond Construction for Heterocycle Synthesis

  摘要：

  A two-step process is described for the union of aromatic imines, conjugated alkynes, and aldehydes that results in a stereoselective synthesis of highly substituted piperidines. This synthetic process has been made possible by defining a unique regioselective functionalization of conjugated alkynes that establishes a suitably functionalized substrate for subsequent heterocycle-forming cationic annulation. Given the flexibility of the coupling process, heterocycles can be accessed through a process that establishes up to four stereogenic centers and four fused rings.

  DOI：

  10.1021/ol902169k

文献信息

• Convergent Synthesis of Piperidines by the Union of Conjugated Alkynes with Imines: A Unique Regioselective Bond Construction for Heterocycle Synthesis
  作者：Ming Z. Chen、Glenn C. Micalizio

  DOI：10.1021/ol902169k

  日期：2009.11.5

  A two-step process is described for the union of aromatic imines, conjugated alkynes, and aldehydes that results in a stereoselective synthesis of highly substituted piperidines. This synthetic process has been made possible by defining a unique regioselective functionalization of conjugated alkynes that establishes a suitably functionalized substrate for subsequent heterocycle-forming cationic annulation. Given the flexibility of the coupling process, heterocycles can be accessed through a process that establishes up to four stereogenic centers and four fused rings.