(5aR,15bR)-2,3,4,5,5a,6,10,15-octahydro-9H-cyclohepta[1,8a]indolizino[8,7-b]indol-7(1H)-one | 1253404-37-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (5aR,15bR)-2,3,4,5,5a,6,10,15-octahydro-9H-cyclohepta[1,8a]indolizino[8,7-b]indol-7(1H)-one
• 英文别名: (1R,16R)-3,13-diazapentacyclo[11.8.0.01,16.02,10.04,9]henicosa-2(10),4,6,8-tetraen-14-one
• CAS: 1253404-37-3
• 化学式: C₁₉H₂₂N₂O
• 分子量: 294.396
• InChiKey: QMGYAIWOPGSBAC-BFUOFWGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  色胺 、 2-Oxo-cycloheptan-essigsaeure 在 (R)-3,3'-bis-(triphenylsilyl)octahydrobinolphosphoric acid 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 (5aS,15bS)-2,3,4,5,5a,6,10,15-octahydro-9H-cyclohepta[1,8a]indolizino[8,7-b]indol-7(1H)-one 、 (5aR,15bR)-2,3,4,5,5a,6,10,15-octahydro-9H-cyclohepta[1,8a]indolizino[8,7-b]indol-7(1H)-one
  参考文献：
  名称：

  Direct Enantioselective Brønsted Acid Catalyzed N-Acyliminium Cyclization Cascades of Tryptamines and Ketoacids

  摘要：

  A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with gamma- and delta-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).

  DOI：

  10.1021/ol101651t

文献信息

• Direct Enantioselective Brønsted Acid Catalyzed <i>N</i>-Acyliminium Cyclization Cascades of Tryptamines and Ketoacids
  作者：Chloe A. Holloway、Michael E. Muratore、R. lan Storer、Darren J. Dixon

  DOI：10.1021/ol101651t

  日期：2010.11.5

  A direct enantio- and diastereoselective N-acyliminium cyclization cascade through chiral phosphoric acid catalyzed condensation of tryptamines with gamma- and delta-ketoacid derivatives to provide architecturally complex heterocycles has been developed. The reaction is technically simple to perform, atom-efficient, and broad in scope. Employing 10 mol % of (R)-BINOL derived chiral phosphoric acids in refluxing toluene allowed the polycyclic product materials to be generated in good yields (53-99%) and moderate to high enantioselectivities (68-98% ee).