(4aR,14bR)-11-methoxy-1,2,3,4,4a,5,9,14-octahydro-6H,8H-pyrido[3,4-b:1,2-i']diindol-6-one | 1253404-41-9

• 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: (4aR,14bR)-11-methoxy-1,2,3,4,4a,5,9,14-octahydro-6H,8H-pyrido[3,4-b:1,2-i']diindol-6-one
• 英文别名: (1R,16R)-7-methoxy-3,13-diazapentacyclo[11.7.0.01,16.02,10.04,9]icosa-2(10),4(9),5,7-tetraen-14-one
• CAS: 1253404-41-9
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: OGJREAXFJDVJKM-CWTRNNRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-甲氧基色胺 、 2-环己酮乙酸乙酯 在 (R)-3,3'-bis-(triphenylsilyl)octahydrobinolphosphoric acid 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 11-methoxy-1,2,3,4,4a,5,9,14-octahydro-6H,8H-pyrido[3,4-b:1,2-i']diindol-6-one 、 (4aR,14bR)-11-methoxy-1,2,3,4,4a,5,9,14-octahydro-6H,8H-pyrido[3,4-b:1,2-i']diindol-6-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).