9-benzyl-8-(iodomethyl)-10-methyl-9-azabicyclo[3.3.2]dec-2-ene | 1092407-86-7

• 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: 9-benzyl-8-(iodomethyl)-10-methyl-9-azabicyclo[3.3.2]dec-2-ene
• 英文别名: (1S,3R,4S,7S)-2-benzyl-7-(iodomethyl)-3-methyl-2-azabicyclo[2.2.2]oct-5-ene
• CAS: 1092407-86-7
• 化学式: C₁₆H₂₀IN
• 分子量: 353.246
• InChiKey: BLLPEOYXJQJAFY-MIGQKNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  9-benzyl-8-(iodomethyl)-10-methyl-9-azabicyclo[3.3.2]dec-2-ene 在 silver perchlorate 、 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以74%的产率得到(2R,3S)-3-allyl-1-benzyl-2-methyl-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines

  摘要：

  A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good yields and further derivatized to polysubstituted indolizidine.

  DOI：

  10.1021/ol8024605
• 作为产物：
  描述：

  9-benzoyl-8-(iodomethyl)-10-methyl-9-azabicyclo[3.3.2]dec-2-ene 在 三氟甲磺酸酐 、 二氢吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 以80%的产率得到9-benzyl-8-(iodomethyl)-10-methyl-9-azabicyclo[3.3.2]dec-2-ene
  参考文献：
  名称：

  Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines

  摘要：

  A new concerted silver ion-mediated Grob fragmentation process is described in which a 1,2-dihydropyridinium ion is formed and trapped in situ with Grignard reagents in a highly regio- and diastereoselective fashion. Using this methodology, 2,3,6-trisubstituted piperidines were synthesized in good yields and further derivatized to polysubstituted indolizidine.

  DOI：

  10.1021/ol8024605