(2-benzoyl-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-6-yl)methanol | 1072433-00-1

• 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-benzoyl-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-6-yl)methanol
• 英文别名: (2-benzoyl-3-methyl-2-azabicyclo[2.2.2]oct-7-en-6-yl)methanol；[(1S,3R,4S,7S)-7-(hydroxymethyl)-3-methyl-2-azabicyclo[2.2.2]oct-5-en-2-yl]-phenylmethanone
• CAS: 1072433-00-1
• 化学式: C₁₆H₁₉NO₂
• 分子量: 257.332
• InChiKey: AYRXSPALGJPRPF-NGFQHRJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2-benzoyl-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-6-yl)methanol 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以90%的产率得到9-benzoyl-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
• 作为产物：
  描述：

  methyl 2-[(E)-{[(1S)-1-(methoxymethyl)-2-methylpropyl]imino}(phenyl)methyl]-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-6-carboxylate 、 苯甲酰氯 在 aluminum (III) chloride 、 lithium aluminium tetrahydride 、 sodium hydroxide 、 水 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以10.7 g的产率得到(2-benzoyl-3-methyl-2-azabicyclo[2.2.2]oct-7-ene-6-yl)methanol
  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

文献信息

• Total Synthesis of (+)-Lepadin B: Stereoselective Synthesis of Nonracemic Polysubstituted Hydroquinolines Using an RC-ROM Process
  作者：Guillaume Barbe、André B. Charette

  DOI：10.1021/ja8068215

  日期：2008.10.22

  communication describes a new tandem metathesis reaction for which an RC-ROM mechanism was experimentally supported. This process was successfully applied to the synthesis of cis-fused polyhydroquinolines enabling a short stereoselective total synthesis of ent-lepadin B.

  该通讯描述了一种新的串联复分解反应，该反应在实验上支持了 RC-ROM 机制。该过程成功应用于顺式稠合聚氢喹啉的合成，实现了对ent-lepadin B的短立体选择性全合成。
• Silver Ion-Induced Grob Fragmentation of γ-Amino Iodides: Highly Stereoselective Synthesis of Polysubstituted Piperidines
  作者：Guillaume Barbe、Miguel St-Onge、André B. Charette

  DOI：10.1021/ol8024605

  日期：2008.12.4

  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.