1-((1R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]oct-2-en-2-yl)-propan-1-one | 152668-77-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-((1R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]oct-2-en-2-yl)-propan-1-one
• 英文别名: 1-[(1R,5S)-8-Methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl]-1-propanone；1-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-2-en-2-yl]propan-1-one
• CAS: 152668-77-4
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: NBLPKIOUMFCZNO-PSASIEDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  8-<(1,1-dimethylethoxy)carbonyl>-2-propionyl-8-azabicyclo<3.2.1>octa-2-ene 在 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.08h， 生成 1-((1R,5S)-8-Methyl-8-aza-bicyclo[3.2.1]oct-2-en-2-yl)-propan-1-one
  参考文献：
  名称：

  Enantioselective Synthesis of Functionalized Tropanes by Rhodium(II) Carboxylate-Catalyzed Decomposition of Vinyldiazomethanes in the Presence of Pyrroles

  摘要：

  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.

  DOI：

  10.1021/jo961920w

文献信息

• 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.