1-[(1R,5S)-8-氮杂双环[3.2.1]辛-2-烯-2-基]乙酮 | 64603-83-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[(1R,5S)-8-氮杂双环[3.2.1]辛-2-烯-2-基]乙酮
• 英文名称: (-)-Norferruginine
• 英文别名: (1R,5S)-2-acetyl-8-azabicyclo<3.2.1>octa-2-ene；(-)-(1R,5S)-2-acetyl-8-azabicyclo[3.2.1]oct-2-ene；(-)-norferrugine；1-[(1R,5S)-8-azabicyclo[3.2.1]oct-2-en-2-yl]ethanone
• CAS: 64603-83-4
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: DYSCFNKIZDWMSK-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 1-[(1R,5S)-8-氮杂双环[3.2.1]辛-2-烯-2-基]乙酮 在 sodium cyanoborohydride 作用下， 生成 (-)-Ferruginine
  参考文献：
  名称：

  Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l-Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

  摘要：

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.

  DOI：

  10.1021/jo9515081
• 作为产物：
  描述：

  (1R,5S)-2-acetyl-8-<(1,1-dimethylethoxy)carbonyl>-8-azabicyclo<3.2.1>octa-2-ene 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 1-[(1R,5S)-8-氮杂双环[3.2.1]辛-2-烯-2-基]乙酮
  参考文献：
  名称：

  Enantiospecific Synthesis of (+)- and (−)-Ferruginine from l-Glutamic Acid. Synthesis of Tropanes via Intramolecular Iminium Ion Cyclization

  摘要：

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.

  DOI：

  10.1021/jo9515081

文献信息

• Wegge; Schwarz; Seitz, Pharmazie, 2000, vol. 55, # 10, p. 779 - 780
  作者：Wegge、Schwarz、Seitz

  DOI：——

  日期：——
• Enantiospecific Synthesis of (+)- and (−)-Ferruginine from <scp>l</scp>-Glutamic Acid. Synthesis of Tropanes <i>via</i> Intramolecular Iminium Ion Cyclization
  作者：Andrés S. Hernández、Adrian Thaler、Josep Castells、Henry Rapoport

  DOI：10.1021/jo9515081

  日期：1996.1.1

  Iminium ions, generated by decarbonylation of N-benzyl-5-[1-(methoxycarbonyl)-4-oxopentyl]-prolines, prolines, undergo intramolecular cyclization to afford 2,4-disubstituted tropanes in good yields. This transformation is also shown to be a stereospecific reaction. The value of these substituted tropanes has been demonstrated by functional group manipulation, leading to the enantiospecific synthesis of (+)-ferruginine, an alkaloid isolated from Darlinga ferruginea, and its unnatural enantiomer, (-)-ferruginine.
• Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles
  作者：Huw M. L. Davies、Julius J. Matasi、L. Mark Hodges、Nicholas J. S. Huby、Craig Thornley、Norman Kong、Jeffrey H. Houser

  DOI：10.1021/jo961920w

  日期：1997.2.1

  A series of enantiomerically enriched tropanes was synthesized by the rhodium(II) octanoate-catalyzed reaction of various N-BOC-protected pyrroles with vinyldiazomethanes. The overall 3 + 4 annulation occurs by a tandem cyclopropanation/Cope rearrangement. Asymmetric induction was best achieved in these transformations by using either (S)-lactate or (R)-pantolactone as a chiral auxiliary on the vinyldiazomethanes. Reactions carried out with the chiral catalyst tetrakis[N-( 4-tert-butylbenzenesulfonyl)-(L)-prolinato]dirhodium (2) provided moderate asymmetric induction, but also resulted in the formation of isomeric azabicyclooctane side products. The utility of the synthetic process was demonstrated through the asymmetric synthesis of(-)-anhydroecgonine methyl ester and (-)-ferruginine.