(2-benzyl-3-methyl-2-azabicyclo[2.2.2]oct-5-en-7-yl)methanol | 1254974-33-8

• 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: (2-benzyl-3-methyl-2-azabicyclo[2.2.2]oct-5-en-7-yl)methanol
• 英文别名: [(1R,3S,4R,6R)-2-benzyl-3-methyl-2-azabicyclo[2.2.2]oct-7-en-6-yl]methanol
• CAS: 1254974-33-8
• 化学式: C₁₆H₂₁NO
• 分子量: 243.349
• InChiKey: RGRKAYDOMZLBNN-QCEMKRCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸酐 、 (2-benzyl-3-methyl-2-azabicyclo[2.2.2]oct-5-en-7-yl)methanol 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 2-benzyl-3-methyl-6-((trifluoromethylsulfonyloxy)methyl)-2-azoniabicyclo[2.2.2]oct-7-ene trifluoromethanesulfonate
  参考文献：
  名称：

  Stereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyridines via Tf₂O-Mediated Grob Fragmentation: Access to Indolizidines (−)-209I and (−)-223J

  摘要：

  Herein we describe the gamma-amino hydroxide Grob fragmentation of the aza-bicyclo[2.2.2]octene 1 using triflic anhydride as the activating agent. The resulting dihydropyridinium ion can react with a wide variety of Grignard reagents, giving access to 2,3,6-trisubstituted tetrahydropyridines (2) with high regio- and stereoselectivities. This methodology has been applied to the short synthesis of natural indolizidines (-)-2091 (3) and (-)-223J (4).

  DOI：

  10.1021/jo1015344
• 作为产物：
  描述：

  (7-hydroxymethyl-3-methyl-2-aza-bicyclo[2.2.2]oct-5-en-2-yl)-phenyl-methanone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以86%的产率得到(2-benzyl-3-methyl-2-azabicyclo[2.2.2]oct-5-en-7-yl)methanol
  参考文献：
  名称：

  Stereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyridines via Tf₂O-Mediated Grob Fragmentation: Access to Indolizidines (−)-209I and (−)-223J

  摘要：

  Herein we describe the gamma-amino hydroxide Grob fragmentation of the aza-bicyclo[2.2.2]octene 1 using triflic anhydride as the activating agent. The resulting dihydropyridinium ion can react with a wide variety of Grignard reagents, giving access to 2,3,6-trisubstituted tetrahydropyridines (2) with high regio- and stereoselectivities. This methodology has been applied to the short synthesis of natural indolizidines (-)-2091 (3) and (-)-223J (4).

  DOI：

  10.1021/jo1015344

文献信息

• Stereoselective Synthesis of 2,3,6-Trisubstituted Tetrahydropyridines via Tf₂O-Mediated Grob Fragmentation: Access to Indolizidines (−)-209I and (−)-223J
  作者：Gérald Lemonnier、André B. Charette

  DOI：10.1021/jo1015344

  日期：2010.11.5

  Herein we describe the gamma-amino hydroxide Grob fragmentation of the aza-bicyclo[2.2.2]octene 1 using triflic anhydride as the activating agent. The resulting dihydropyridinium ion can react with a wide variety of Grignard reagents, giving access to 2,3,6-trisubstituted tetrahydropyridines (2) with high regio- and stereoselectivities. This methodology has been applied to the short synthesis of natural indolizidines (-)-2091 (3) and (-)-223J (4).