(4R)-2-methylenyl-4-methyl-6-cyanoquinolizidine | 852520-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹嗪类
• 英文名称: (4R)-2-methylenyl-4-methyl-6-cyanoquinolizidine
• 英文别名: (4S,6R)-6-methyl-8-methylidene-1,2,3,4,6,7,9,9a-octahydroquinolizine-4-carbonitrile
• CAS: 852520-69-5
• 化学式: C₁₂H₁₈N₂
• 分子量: 190.288
• InChiKey: OUXHGPZCNODMOL-LWALXPGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4R)-2-methylenyl-4-methyl-6-cyanoquinolizidine 在 sodium cyanoborohydride 作用下， 以 乙腈 为溶剂， 以86%的产率得到(R)-4-Methyl-2-methylene-octahydro-quinolizine
  参考文献：
  名称：

  Cascade Iminium Ion Reactions for the Facile Synthesis of Quinolizidines. Concise Syntheses of (±)-Epilupinine and (−)-Epimyrtine

  摘要：

  Several novel cascade processes have been designed and developed that involve sequential reactions of imines and iminium ions to form substituted quinolizidine ring systems in a single step from simple and readily available starting materials. The utility and promise of these cascade reactions is evident from their application to extraordinarily concise syntheses of the representative quinolizidine alkaloids epilupinine and (-)-epimyrtine.

  DOI：

  10.1021/ol050544b
• 作为产物：
  描述：

  (R)-4-(trimethylsilylmethyl)pent-4-en-2-amine 在 4 A molecular sieve 、 三氟乙酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 (4R)-2-methylenyl-4-methyl-6-cyanoquinolizidine
  参考文献：
  名称：

  Cascade Iminium Ion Reactions for the Facile Synthesis of Quinolizidines. Concise Syntheses of (±)-Epilupinine and (−)-Epimyrtine

  摘要：

  Several novel cascade processes have been designed and developed that involve sequential reactions of imines and iminium ions to form substituted quinolizidine ring systems in a single step from simple and readily available starting materials. The utility and promise of these cascade reactions is evident from their application to extraordinarily concise syntheses of the representative quinolizidine alkaloids epilupinine and (-)-epimyrtine.

  DOI：

  10.1021/ol050544b

文献信息

• Cascade Iminium Ion Reactions for the Facile Synthesis of Quinolizidines. Concise Syntheses of (±)-Epilupinine and (−)-Epimyrtine
  作者：Shawn M. Amorde、Andrew S. Judd、Stephen F. Martin

  DOI：10.1021/ol050544b

  日期：2005.5.1

  Several novel cascade processes have been designed and developed that involve sequential reactions of imines and iminium ions to form substituted quinolizidine ring systems in a single step from simple and readily available starting materials. The utility and promise of these cascade reactions is evident from their application to extraordinarily concise syntheses of the representative quinolizidine alkaloids epilupinine and (-)-epimyrtine.