(2S,3R,6S)-3-allyl-1-benzyl-2-methyl-6-(2-phenyl-1,3-dithian-2-yl)-1,2,3,6-tetrahydropyridine | 1254974-52-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R,6S)-3-allyl-1-benzyl-2-methyl-6-(2-phenyl-1,3-dithian-2-yl)-1,2,3,6-tetrahydropyridine
• 英文别名: (2S,3R,6S)-1-benzyl-2-methyl-6-(2-phenyl-1,3-dithian-2-yl)-3-prop-2-enyl-3,6-dihydro-2H-pyridine
• CAS: 1254974-52-1
• 化学式: C₂₆H₃₁NS₂
• 分子量: 421.671
• InChiKey: LWAZUYMHDJYZAI-PWWKTKHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-phenyl-1,3-dithiane magnesium bromide 、 3-allyl-1-benzyl-2-methyl-2,3-dihydropyridinium trifluoromethanesulfonate 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 (2S,3R,6S)-3-allyl-1-benzyl-2-methyl-6-(2-phenyl-1,3-dithian-2-yl)-1,2,3,6-tetrahydropyridine 、
  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).